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The Best Ever

Category: Anal Sex
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I knew before it was over that I had to write this story, to cement the memory in my mind. To somehow make this surreal experience that once resided only in my darkest fantasies even more real. This was a once in a lifetime experience that’s simply too good to let fade with time. So here’s my story…

I met Isabella while competing in a sport we both love. She’s a stunningly beautiful blonde, about 5’10” and 145 pounds, with flawless skin and an ass to die for. She’s also smart and witty, with a million watt smile that draws people to her like bees to honey. We went to the same events and occasionally even competed against each other. Over time we grew close. Very close. We eventually started traveling together to competitions across the country. Her husband didn’t seem to mind and neither did my wife, so long as they weren’t expected to tag along. Neither of them cared much for our sporting endeavors and preferred that we do it without their attendance.

It was on one of these trips that the subject of sexual fantasies came up. Both our spouses we discovered were pretty staid in their sexual attitudes. Bella and I however? Not so much. We talked quite openly, but I held back. I wasn’t sure I wanted to share my deepest fantasies. I was afraid she would think me some sort of twisted freak. Eventually we even hooked up a couple of times, but ultimately decided that our friendship was too special to risk screwing it up with a complicated relationship. We still managed to talk about sex frequently though, and even shared amazing kisses. Her lips are like sunshine from heaven. They brighten even the darkest of days.

Once, when I was out of town for a work assignment, we were talking on the phone and the subject again came up about fantasies. I think she could tell I was withholding, and she wasn’t having that. Bella can be quite demanding and persistent. As she usually does, she got what she set her sights on. It took quite a while to spill my secret. I wasn’t sure if she’d understand, or even worse, be grossed out. I was very nervous about telling her, but she’s a great friend whom I trust implicitly, so I finally decided to let my secret out. I told her that one of my deepest and definitely unfulfilled fantasies was to have a woman take my ass.

Bella is a very open and progressive woman, but it was still a shock and relief to hear her say without skipping a beat, “Oh I could do that!” I was actually trembling inside as we discussed having her take me back there. She wasn’t just willing to help me realize a fantasy, she sounded downright enthusiastic about it. We made plans to do it for a few weeks later and the wait was excruciating.

Bella is a certified massage therapist and her hands are amazing. She can delight and torture at the same time. I swear they’re made of 49% demon, 51% angel. After an hour with her you have to pour yourself off the table. We decided that she would come over to my place to give a massage and we’d go from there. She laid the ground rules first, which included her being in control and that I couldn’t touch her. It was a tough thing to agree to, but well worth the compromise as I’d soon discover.

When Bella arrived she had me strip and lay on the bed. She massaged my back for about 45 minutes, which felt fantastic. She had stripped down to her sexy bra and boy cut panties. Watching her work on my back in the dressing mirror next to the bed was quite erotic. I was nervous and excited at the same time, but the massage helped calm me for what was to come. After the massage, she had me lay on my back on the towel with my head propped up on a pillow. There was a wet spot on the towel where my cock had been trapped during the massage. This did not escape Bella’s attention!

As she stripped out of her bra and panties, I once again marveled at how a 36 year old mother of two could have such a fantastic body. Her long, lithe frame is accentuated by small pert breasts, topped with delicate nipples that beg to be suckled. Her light caramel skin was glistening and begging for my fingertips, but that would have to wait for another day.

As we had discussed while preparing for my fantasy day, Bella was provided access to my toy bag. She opened it like a child opening a gift on Christmas Eve. She was surprised by my assorted collection of toys and quickly went about the task of placing them in the order she intended to use them. She was particularly taken with a glass popper, which I told her she could keep. Bella rewarded me with one of her classic displays of delight. She has a way of giggling, smiling broadly, tossing her head and rocking from side to side when she’s truly happy that’s one of the world’s great wonders.

With the preliminary business taken care of, Bella climbed between my legs with an impish grin on her face. Her well oiled hands massaged my groin for a few minutes while she teased me unmercifully, not that I needed it at that point. She eventually lowered her head and started using her mouth in a slow and deliberate manner at the crease between my thighs and scrotum.

Bella kept using her tongue to bathe my tender skin with slow, sensual flicks as she kept going lower and lower. She paid particular attention to the sensitive spot between my balls and my crack. After what seemed like forever, she raised my legs up over her shoulders and I could feel her hot breath on my ass. She gazed into my eyes with a look of pure lust, then gently started to swirl her tongue into my ass crack. She began slowly and softly, circling ever closer to my anus with each tender pass of her tongue. After what seemed like an eternity, I felt the tip of her hot pink tongue make contact with my rosebud. It was like an electric flash. I moaned audibly as the most exquisite sensation I’d ever felt emanated from my asshole and shot straight up my spine.

I could see her face over my rock hard cock and she had this sexy, devilish look in her eyes. Bella had discovered my secret desire, and now she had discovered its point of origin. I could tell I was in for the ride of my life as she settled in for the feast. Bella started deliberately, but before long she began to eat my ass with a hunger. I’d never really had a desire to go down on a woman’s ass before, but watching her dive in with such zeal made me reconsider. I knew from the many kisses we’d shared that she has an incredibly talented tongue, but this was off the scale.

Every time I thought it was the most incredible sensation I’d ever felt, she’d change what she was doing and it would get even better. She must have done that for about 5 minutes before she rose up with a grin on her face. In a voice that would melt stone, Bella told me to stroke my cock. I was dripping clear drops of pre-cum like I’d never seen before. I slowly started to stroke it and she resumed rimming my ass even more aggressively. Bella began forcing her long tongue deeper and deeper into my ass. It was heaven on earth. It felt like a white hot poker was drilling to my very core. I can only hope a woman feels that good when I go down on her. She was kneading my ass with her hands and prying my cheeks apart, trying to get so far into my ass with her mouth it was as if she were consuming me.

I was moaning and twisting from the indescribable pleasure Bella was giving me. I felt myself grab my legs and spread them upward so she would have even better access. I felt like a wanton slut who would do anything to feel this good forever. It felt incredibly submissive, yet utterly liberating at the same time. I was laid bare before her and she was obviously reveling in my predicament.

Eventually, Bella’s fingers began circling my anus. There were butterflies in my stomach as I pondered the fact that she was about to penetrate me where no one else had been before. After about 10 minutes of this torture, she took my cock in her mouth and sucked me deeply as she gently slid her index finger into my ass.

She slowly worked her finger into my ass, being careful to not scratch me with her beautifully manicured nail. I was gripping the sheets and going wild. When she had her finger fully lodged in my ass, she turned her hand over and drew her fingertip across my prostate. I almost came off the bed! She knew she had found my on button, so she sat back and worked it. After a few minutes, I told her to use some lube as her saliva was starting to dry up. She grabbed the bottle of lube and theatrically dripped it onto my ass while she slowly withdrew her finger. Her devilish smile told me I was in for more.

Once she had massaged the lube in, she really started working my ass with her finger. I was clawing the sheets and moaning “More…” At that point Bella pressed a second finger into my ass. I could feel the extra pressure stretching my anus and it was part pain, yet pure pleasure. She was watching my cock intently and began working my prostate over really good. My cock was running a steady stream of pre-cum. She found a way to stroke my prostate that was like moon-walking your index and middle finger across a table, back and forth in a rubbing motion. She began milking my prostate with her fingers until white, hot cum started pouring out onto my stomach.

This turned her on like no tomorrow and she really started banging my ass with her fingers. I was going out of my mind. The feeling was otherworldly! I was moaning, clawing and panting. It felt like I was turning inside out and Bella loved every second of it. Throughout this she had a look on her face like it was the best thing she’d ever done. Her obvious enthusiasm amped the intensity level to the max.

She finally turned her fingers upwards towards my prostate and started stroking my cock with her other hand. She soon had a good rhythm going. I would raise my ass off the bed and her fingers would slide mostly out of my ass as my cock stroked into her hand. This would make my ass cheeks clench as if they were desperately grasping for her fingers to stay inside. As I drove my ass back down, it would impale me on her fingers as her hand up-stroked my cock. That’s when she started saying “Cum for me” over and over in a voice that was the most sensual thing I’ve ever heard in my life.

My ass was slamming up and down on her fingers like a jackhammer. I began the longest, most torturous ascent to climax I’ve ever felt. It seemed to take forever as Bella chanted “Cum for me” again and again in the softest, sexiest voice on earth. I was literally out of my mind as I reached the top and came in her hand in the most intense orgasm ever. I was dizzy and my head was spinning. It seemed to last twice as long as ever before. I was sweating, panting, groaning and out of breath. I was literally spent. I collapsed in a heap as she slowly slid her fingers out of my well used ass.

When I opened my eyes, she was grinning like a Cheshire cat. Bella had the nerve to ask “Well, how was it?” I was too spent to even respond. She got up, came over next to my head and grabbed my wrist. She said “Just in case you were wondering if I enjoyed it as much as you…” and drew my index and middle fingers across her soaking wet pussy. She bathed them in her nectar. I smelled my fingers and sucked her juices, which was pure ecstasy.

I tried to get her to let me return the favor, but she refused. She said this was her fulfilling my fantasy and she didn’t want to do more than that. We never even made it to the toys. What she did with her mouth and fingers was more than enough. We got dressed and I took her to lunch. She grinned throughout the entire meal. She asked me if I had any other unfulfilled fantasies, and my mind immediately began to consider the possibilities.

I don’t know when or if we’ll ever do it again. Even if we don’t, it was the fantasy of a lifetime, come true. I still marvel at what I’ve done to deserve such an angel in my life. My friend, my Bella, my Goddess, she’s truly one of a kind!

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