“I know what I promised and I will try. You want my ass, don’t you?” Katie asked.

“Of course”, I replied.

“I’ve tried twice, with different guys. It just hurt and I made them stop. So, you can try, but I don’t know if I can do it”, she said.

“I wanted this day to be all about your pleasure, not pain. You have to trust me. I won’t hurt you. If you feel any pain at all, know that I will stop immediately. I will take things very slowly, that’s why it hasn’t been successful before, I suspect. Just hang in there with me and I will give you the most amazing orgasm of your life”, I told her.

I told Katie to lift her hips up and eased two pillows under her, lifting that beautiful ass up for me to play with. She was face down, mostly spread eagle, taking up most of the bed. That was ok, the place I wanted to be wasn’t covered and I moved to lie between her legs. I started kissing her left butt cheek, gently, very soft kisses. While I covered that cheek with my lips, I was running my hands up and down her back. Up the middle, down the sides; up the sides, down the middle. I then moved to her right cheek.

Eventually, my tongue emerged and I grazed her wonderful skin with it. Light touches, teasingly at first, then more forceful. I stopped massaging her back and used my hands to separate her cheeks. What a beautiful sight, I thought, as my cock once again began to stir.

As I lowered my chin to the bed, I noticed she was getting very wet again, her wetness was pushing the few remnants of my cum out to her perfect little lips. Gently grazing her slit, my tongue barely touched those smooth lips, licking upward towards her asshole. As I teasingly circled her cute little rosebud with my tongue, I felt her tense up. “Relax, just trust me”, I whispered.

“That just seems so intimate, so personal. No one has ever licked me there before”, Katie murmured.

I replied, “Just stay relaxed and enjoy it.” Keeping my tongue focused on teasing her ass, I reached for the small vibe. Turning it on very low, I started using it on her pussy lips, sliding it between her length wise. I turned it to penetrate her pussy and only slid about half way inside her.

She moaned softly. I don’t think she had the energy to make a louder sound. Leaving the vibe alone, I reached for her cheeks with both hands. Her tight pussy held the toy in place as I spread her ass so my tongue would have full access. I licked her hole, up and down, lubricating it with my saliva. Katie moaned again but didn’t move. A few licks later, I eased my tongue in her ass. Slowly and very gently, I started tongue fucking her ass.

She groaned with pleasure, as she found the strength to finally move. Katie moved her feet as wide as she could, leaving both of her holes wide open for my access. Each time my tongue went into her, I went a little further; widening her ass a little bit more with each stroke. I placed my hands on her butt cheeks, index fingers on the edge of her asshole, using them to spread her even more. When my tongue was worn out, I replaced it with my pinky finger. I had lubricated it well with my mouth and slowly worked it fully inside her.

Katie seemed to really be enjoying it, moaning and groaning. Her hole had relaxed somewhat around my finger. I reached down; removing the still slow buzzing vibe from her pussy, made sure it was well lubed, and very slowly started easing it inside her ass. It took a few minutes to work it in, stopping every quarter inch to make sure she wasn’t in any pain. Detecting none, I had most of it in and started fucking her with it.

Her pulse was increasing and her breathing was coming in shorter pants. Low, long moans and groans were now emitting from her. I fucked her until her ass muscles were as loose as they were going to get, probably about 10 minutes. Asking if she was ready to try some cock, she hissed, “Oh God, Yes”. 

Leaving the vibrator inside her, I raised up, placed my hands on her hips and brought her to her hands and knees.

I reached around and removed the pillows, grabbing the bottle of lube for myself. Quickly coating my entire shaft, I slowly removed the vibe and placed plenty of lube in and around her hole. I guided the head of my cock to her ass and began to enter her.

Easing the head inside her perfect ass, I stopped, letting her adjust to my cock. “Are you ok?” I asked.

“Almost perfect”, Katie replied. I slid more cock into her, stopping about half way, checking for any sign of discomfort. Detecting none, I continued slowly sliding my cock inside her until my balls were resting on her pussy. I was now fully and completely buried in her ass.

Stopping to make sure Katie was ok, I reveled in the moment. Dear God, if her pussy was Cadillac, being inside her ass was pure Rolls Royce! Being inside her, my cock felt like winning the Super Bowl and the Daytona 500 at the same time. If I had not cum 3 times already today, the simple act of thrusting my hard cock inside her ass would have made me spew cum right then, in one stroke.

“Are you comfortable?” I asked Katie.

Her breath was taken in short pants, but she managed to get out, “Oh my God! I feel so full, so complete. I never knew a cock in my ass could fell so good. Please, fuck me!” I was happy to comply with that request!

I pulled back and set a very slow, steady rhythm. I wanted this to last, but I knew an ass this great would milk me dry in no time. I fuck her wonderful ass for about 10 minutes, slowly increasing the speed of my thrusts. Katie’s ass cheeks were bouncing back and forth in sync with our moves. It was a beautiful sight. Knowing I was getting close, I reached for her shoulders and pulled her into a kneeling position. Now we were both kneeling on the bed, spooned, her beautiful ass resting on my hips, my cock buried inside her ass. I was only able to take short strokes, so I reached around with my right hand and found her clit. Damn, her pussy was dripping, that wonderful love juice was running down her inner thighs. It made me so fucking horny to know I had caused it. Spreading her lips with two fingers, my middle finger gently stroked her clit.

She was making sounds I had only heard a few times before. Every time she exhaled, “Uhh, uhh, uhh” Katie was about to cum, with a cock in her ass. Stroking her clit, making small circles with my very wet finger did it! “Oh FUCK, I’m CUMMING”. And she did.

The climax hit her like a baseball bat, her legs tried to shoot straight out. Luckily, I grabbed her waist and held her close to me. Each pulse hit her pussy and ass forcefully. About the third time her asshole contracted around my cock, I orgasmed. Hot, long streams of sperm were erupting from my cock, deposited into her ass. We were in perfect unison, her ass contracted, my cock pulsed, contraction, pulse. We both finally came down, orgasms subsided. My legs were killing me, so I eased her forward, my cock still inside her.

Once I was lying on top of her, I realized the wet spot on the bed had gotten much larger. I reached underneath her and found her clit once again. Holding my cock steady, not thrusting, I fingered her slit until she had another orgasm. The feeling of her ass muscles contracting around my now shrinking cock was pure heaven.

Katie was completely spent; face down, spread eagle on the bed. I removed my cock from fine ass and looked around. Sweet nectar from her pussy was halfway down her thighs. The wet spot on the bed was the size of a basketball. I quickly reached for the camera. My sticky cock cream was leaking out of her ass, running down those perfect pussy lips. Katie had bent and pulled her left leg up and I had a so perfect view. I snapped pictures until my cock was limp and most of my cum was visible.

I showered, woke Katie and she showered. I took photos of her in the shower. She got dressed and was ready to leave.

“I’ll talk to Jennifer; she’s going want you bad. And thank you for showing me anal, I had no idea it could be so good.” She turned and walked out, returning to her boyfriend……..