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I’ll never forget the night I met Dara. Dara was a lot of firsts for me. My first older woman (I was 20, she was 27), my first black woman, and my first anal fucking experience.

My friends and I were out on a night on the town because I was headed off to Japan to teach English for a year. We headed out to this new bar that was getting a reputation for being a cougar bar. My friends dared me to see if I could get a genuine cougar but I’d already had my eyes on Dara the second we walked in the door. She was small and petite but with these amazing curves that made me think very dirty thoughts. Her ebony skin made her seem like only a shadow in the dimly lit bar but she had eyes that glowed with desired and lust - something I had never seen on a woman before.

I played it cool at first as I watched her on the dance floor with her friends. She really knew how to move and I was hoping that would carry on later in the night. The sway of her full hips had me hypnotized. I figured she had to come off the floor eventually so I stood near the beer girl and watched for her. When I saw her leave, I quickly paid for a cold one and headed towards her.

I caught her as she reached her table and put the beer in her hands. She eyed me up and down, grabbed my hand, and pulled me out onto the patio. The music was quieter so we began to talk and flirt.

It was only an hour later when we headed back to her downtown condo. Apparently she knew what she wanted and I was it. I had no clue that anal fucking was at the forefront of her mind.

The door was barely closed and we hadn’t even kissed yet before she was taking her clothes off. She pushed me against the wall and had my pants down around my ankles. She began to lick by balls and suck at my cock. I couldn’t believe how fast she got me hard and I’d never felt someone suck me off so well that it made me want to come within minutes.

She stopped just short though and without a word she led me to her room. She wasn’t a talker this woman - she was a do-er. She wasted no time pushing me to the bed, then straddling me. Her cunt was dripping wet and I watched my dick disappear in one swift movement, all the way to the balls, inside her. She rode me nice and slow at first. Then she got faster and faster. She was rubbing her clit like crazy and I thought she was going to cum, but suddenly she stopped.

She turned around so I could see that gorgeous ass and grabbed my dick. I thought she was going to slide it back into her pussy but she just rubbed it over her lips and then aimed it at her puckered little hole. First, just the head of my dick slipped in and I thought, “Holy shit - she’s going to fuck me with her ass!” And she did. Slowly but surely she pushed against my cock and took it all. I could believe that this hot ebony babe was into anal fucking!

It was fucking amazing. Her ass was tighter than anything I’d every felt. I had to concentrate hard on not cumming but I couldn’t help pumping her a little. She was pulling at her nipples and rubbing her clit again. She began riding my cock with her ass fast and she took it deep and I just couldn’t take it anymore. I knew that this anal fucking was NOT her first time! I came deep in her ass and she was right behind me with an orgasm that gripped my tool and sucked every last ounce of energy out of me.

She disappeared into the bathroom and I could hear her cleaning herself up. When she came out she kissed me on the cheek and thanked me. It was like anal fucking was second nature to her.

“Thanks hon. That was great. You fuck pretty good for a white boy. Do you need money for a cab?”

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I’d been after my girlfriend to have anal sex for months but she always turned me down – at least a dozen times. I guess the pressure was kinda getting to her because she told me she wanted to “take some time off.” That’s girl talk for, “I’m breaking up with you but I’m too chicken to do it properly.”

Well, I’ll be damned if not even a week later her best friend didn’t come to see me. Kathy had hung out with us lots and I’d always admired her hot little body. She was really cute and always wore clothes that showed off her figure.
She came into my place and told me how sorry she was that Brenda had broken up with me because she wouldn’t see me as often. Then, we chatted for awhile. Finally, she got to the point of why she was really there.

“You know, Brenda told me why you guys broke up.”

“Ya – you must think I’m a real ass.”

“No. I actually didn’t get it. I told her she should try it.”

“Ya? You ever tried it?”

She shook her head. “No. Remember when I was going out with that guy, Mike? I tried to get him to go there but he said that was for fags.”

My dick was starting to get hard just knowing that she was into anal sex and actually wanted it.

“He’s an idiot.”

“Ya.”

She was quiet for a moment.

Then she said, “But you know, since we’re both single…”

“What about Brenda?”

She smirked and came over and straddled my lap.

“I won’t tell if you don’t tell.”

“Not a word,” I promised as she slid her top over her head.

My hands went to those hot little tits right away. She was smaller than Brenda but who gave a shit – she was going to let me have anal sex with her!

I started sucking at her nipples and she got really squirmy on my lap, rubbing herself against my dick, which of course was rock hard by now.

I figured she was ready to get naked by now so I said, “C’mon. Let’s go into the bedroom.” She didn’t make any complaints and headed down the hall right away. Guess she wanted it as badly as I did.

She quickly removed her clothes and started to work on my cock. First a little hand work and then she started sucking. Her ass and pussy were right in front of my face so I started to finger her. She was already dripping wet and I had no problem sliding a couple fingers in there. She moaned with her mouth full of my dick so I added another one. She was moving back and forth over my hand and it looked great but I was watching her puckered hole. I brought my thumb up and started to rub it.

“Wait…”

Shit, I thought, she’s chickening out. No anal sex for me.

But she wasn’t. She reached over to the side of the bed where she’d dropped her purse. She came back with a little bottle of lube.

“Use this,” she said and went back to sucking my cock.

So, I squirted a healthy amount over her little rosebud, slid my finger back into her cunt and popped my thumb into her ass.

She muttered something over my cock but it didn’t sound like “stop” so I kept going. I pumped away at her juicy twat and her lubed up ass until I couldn’t stand it anymore.

“Kathy, c’mon. I’m going to cum and I want to get inside your ass.”

She sat up and smiled at me. Grabbing a condom from my bedside drawer, I slid it over my cock. I was hoping I’d last long enough to really enjoy it.

Kathy got on all fours in front of me and said, “Just remember to go slow ok?”

I slid into her pussy first. It felt damned good but I didn’t want to waste too much time there so I headed for the back door. I pressed the head against her tight ring and at first it wouldn’t give.

“Push harder,” she said.

I did and it was almost like a pop. She grunted really loudly, but she didn’t’ tell me to stop. I slid in a little more. Fuck, her ass was tight. With each stroke, I thrust a little deeper, a little harder. I couldn’t believe I was finally fulfilling my anal sex fantasy.

Her hand moved to her clit and began to rub. Although her face was buried in the pillow I was pretty sure I could hear her say, “Yes, yes…” and “Fuck…” over and over again. Pretty soon she was backing her ass up against my cock. I knew I couldn’t hold back for much longer so I was really glad when her body started shaking and her muscles started to clench around me. It was the greatest thing I’d ever felt. I kept pumping away into that hot tight space until I came harder than I had ever cum before.

Finally, I let my cock slide from her ass and we both collapsed.

“Promise you won’t tell Brenda that we had anal sex?”

I laughed. “Brenda who?”

She smiled.

“Does that mean we can do it again?”

Christmas is a time for fun and a time for presents and for all sorts of good cheer. It seems to put everyone in a good mood. But you know what it does to me? It makes me horny. While everyone else is getting excited about what they are going to have under the tree or the parties they are going to go to, I’m getting wet over the present I have under my skirt. Now, I have to decide who to give it to.

I haven’t decided who is going to be my annual Christmas fuck yet though. There’s this yummy girl that works on the third floor of my office that I’ve been going for coffee with. She swears she’s straight but…that’s just a challenge right? I happen to know that she’s aching for a good orgasm – her husband has forgotten what going down means apparently. How can a man not do that? The scent of a woman when she’s excited has got to be the most arousing smell in the world. I can practically feel my fingers sliding into her wet puss and hear her sigh. She’s got one of those voices that just turns me to mush.

But then there’s this you. Hmmm. You work in a building a couple blocks down from where I work and we kept running into each other at the Starbucks. And eventually we talked and that turned into exchanged emails and since then I’ve found out that we have something in common – a love for anal sex. You know, you’d think most guys are into that but some of them are just scared to go there. And it’s been awhile since I’ve met a guy that truly knows what he’s doing when he’s using the backdoor. You know what I mean girls – the kind of guy who isn’t afraid to take his time. A little finger play, a little tongue, a lot of tease – it just makes it so much better when you finally slides your cock into my ass nice and slow so that I can feel every inch of your flesh as it enters me.

I have been having this fantasy about you. I’ve been fantasizing that we are at the same bar for our Xmas parties and…well, let’s just skip right to the good part and say we head home early…together of course. A couple of drinks back at my place and things get nice and heated up. And pretty soon inhibitions are gone – along with the clothes. Everything except for the cute little Santa outfit under my clothes. Doesn’t matter that I still have the bra and panties on though because the first thing on my mind is your cock.

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I always like to start things off with a blowjob. There’s just something about the feeling of a man growing hard in your mouth. I love it. I love to see your excitement rise as I lick my tongue up and down your shaft, teasing you, taunting you almost with what you’re going to get. When I feel your pole start to twitch, that’s when I let you feel the heat of my mouth. I encompass just the head with my lips at first and I run my tongue all around the round tip. It’s so arousing to see you get excited when I do that and to feel your struggle to keep control. Then I take more of your cock into my mouth, slowly, until I’ve reached the base. And then it is just a matter of taking you as far as you can go without cumming. Sometimes I completely stop and just hold you as deeply in my mouth as I can handle and I use my tongue to drive you crazy, running it up and down the underside of your cock until you start to move your hips, wanting more.

But this isn’t just about you, you know. I need some pleasuring, too. I push you back on the couch and slowly remove the bra and panty set, leaving the stocking, heels and Santa hat on. I slide my hands over my breasts as I approach you and then straddle you. I want you inside me – but I want it my way. I pull your hands over your head so that you can’t touch me. I know you could escape if you wanted to but I know you won’t because you’ll be having too much fun. I let my breast run up the side of your face and let my nipple skim your cheek. Then I bring it closer to your mouth and you move your head so that you are suddenly sucking at it feverishly. It’s just a little bit rougher than I normally like but tonight I am so worked up that it just gets me hotter. I need more…

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With one hand still holding your arms above your head and my nipple still in your mouth, I reach between my legs and find your cock, still hard and waiting for some attention. I slide it inside my pussy and thrust my hips against you so that I take you all inside of me in one motion. Fuck – that feels so good. For a moment I just stay still, enjoying the feel of your teeth grating against my sensitive flesh and squeezing you dick inside my warm, wet walls. I begin to grind against you, rising and falling and pressing my clit against you. I have full intentions of making it last but my speed is rapidly increasing as I get more and more excited.

Suddenly you get excited and pull your hands away from mine. You grasp the flesh of my ass and thrust inside me. I know I am so close to coming and I really have been thinking about you fucking my ass for so long. I tell you I need more and you know just what I mean.

You position yourself behind me and I raise my leg so it rests on the back of the couch. As I feel the head of your cock rubbing against my puckered hole I begin to rub my clit. And then I feel that slight burn and push as the head of your dick slides past my anal ring. And inch by inch I feel you fill my ass. It’s the most erotic thing in the world and I sigh with complete lust as you pull your cock almost completely out and the back in again – faster this time. Soon, you’re driving your dick inside my ass with wild abandon. I’m frigging my clit and getting closer and closer to coming. But it isn’t until you reach up with one hand to find my breast again – and that hard little nipple that you tormented with your mouth earlier. As you fuck my ass your hand squeezes my breast and then you pinch the nipple – hard enough to make me lost my breath for a moment. As you twist and pull it is almost torturous – but in such a good way.

That’s when I totally lose it. Every muscle in my body clenches up as an orgasm rips through me. You can feel every shudder as I cum and with one last pinch, one last thrust, you’re right behind me.

Hmmm – so who should my Christmas fuck be this year?

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