On the Side Helped With Her Backside (A)

This post is about anal sex (A).


Earlier in the summer, Kate and I moved gradually towards my dreams of absolute buttfucking blissfulness.  My tiny little 4’8” Asian angel is quite sensitive. To say her beautiful, deep brown o-ring is exceptionally tight would be quite the understatement.

As the weeks passed, we made slow progress, measured in millimeters, penetrating only slightly deeper into her sweet rectum.  I knew the whole process had tested her comfort zone. I continually looked for any information I could find that might make the process more comfortable.

Watching videos and reading articles from sexologists online helped a lot. It seemed fucking her ass while spooning sideways, or even missionary, could be more comfortable than taking her from behind. It seemed logical that the body positioning of spooning would naturally limit the depth of penetration. This was certainly true compared to drilling her full-on from behind.  When I discussed this with Kate, she was all for giving it a go that night.

We proceeded through our normal rituals.  I started by rubbing a mild numbing agent on the outside of her anus, giving it five minutes to kick in.  Then I inserted my index finger, slowly thrusting in and out while making circular motions into her tunnel of joy.  Next, I moved up to my middle finger and repeated the same slow, thrusting circular motions into her asshole. (Being understandably skittish, Kate has not wanted me to put two fingers into her simultaneously.)

Our smaller dilator is about four inches long and an inch wide. I lubed it with a thick, water-based lube, and a 2% lidocaine numbing agent.  That amount of lidocaine does a nice job of taking the edge off, ever so slightly. It’s not so strong that Kate would not feel any tearing or other concerns. This has never been an issue.

After five minutes, I put in a dilator about an inch longer and a quarter inch wider.  Her sphincter always puts up a little fight as I penetrate her ass with this one. I noticed this getting ever so slightly easier over time, much to my delight.  After ten minutes with that dilator in, I gently withdrew it, and checked for signs of “biological material.” Finding none, I knew her ass was ready to get fucked.

To prepare for the main event, Kate dropped off the bed to her knees and took my cock into her mouth. She bobbed her head back and forth, wetting my dick and taking it continually further into her mouth. I reached around behind her to grasp the back of her head and pulled her head down my cock. Gently but completely, I thrust it into the depths of her throat.  With some slow little mini-thrusts, I was hard enough to fuck her ass within just a few seconds. 

Kate crawled onto the bed and held onto our loveseat at the bottom of the bed. She was on her left side, her knees bent a little upward, and her beautiful, round badonkadonk looking right at me.  I pumped four full pumps of the lube into my hand and slathered up the length of my cock. Obviously, it was important to make sure it was more than sufficiently wet.  Kate’s comfort is always paramount. 

I jumped up into the bed behind her and inserted my middle finger into her tight little asshole. Again, I slowly thrust in and out with circular motions.  Eager to try this new way to lovingly invade my soulmate, I pressed my cock head into her o-ring. As I increased my pressure, her sphincter began to accept its inevitable fate; my cock slowly eased into her tight asshole.

It was a little bit of a task to adjust to this new position of lying on my left side. Still, I pressed ever so slightly deeper, little by little, into her rectum.  As my movements lengthened, her inner sphincter relaxed nicely. I slowly picked up the pace of my thrusting.

“This is the best yet,” said Kate. I felt the excitement of her beginning to enjoy my intrusion into her backside.

“Push it deeper inside of me,” she said. This was the first time I had ever been directed to do such a thing. To say I was happy to oblige her would be the understatement of all time.

“Push it all the way into me,” Kate moaned softly, and I realized I was living in a glorious dream.

I moved with stronger thrusting into her rectum, and I heard her gasp, feeling her body twitch a little.  While backing off a little, I was still pumping in and out of her. The feel of this previously uncharted rectal territory had to be savored.  I continued for a couple more minutes of slow-to-moderate-paced incredible ass fucking.

My climax neared, and I told Kate I was about to cum. I released my sperm to swim into the depths of the newly-stretched portions of her digestive tract. I also got vocal with some primal groaning, savoring the incredible feeling of pumping my cum into my lovely wife.  Kate began to giggle, always amused at what she calls my “antics” during orgasm. But it is just me freely letting myself go.

I pulled tightly against Kate and held her close for several minutes, softly kissing the back of neck.  My cock had gone limp and slid out of the warm caress of her rectum.  Eventually we got up and started moving, grabbing some water we had on our dresser.  I asked Kate how she liked her ass fucking this time.

“Oh, that was a 9 out of 10.  It was fantastic.” she replied.

Undoubtedly, Kate had been providing me with her ass for my pleasure and benefit.  I don’t know how the entire process had been for her, but I know it was uncomfortable at first for sure.  For the first time, I could tell from her body language and conversation that she unquestionably enjoyed getting her ass fucked that night.  That filled me with excitement, knowing I would almost certainly have many future instances of reliving that rectal reaming.

In fact, she shortly thereafter hopped up onto our bed, spread her ass cheeks wide open and pointed towards me, and asked me if she could have a second round.  I knew Kate was being a little cock tease, as I was pretty sure I wasn’t capable of getting hard again in such short order.  While looking at her beautiful but gooey, sloppy (thanks to me) brown rosebud, nothing would have pleased me more than another round of tender, loving sodomizing my precious bride, but I didn’t think I could make it happen.

“You like your cock up this Philippine ass?” she playfully asked me in her soft, sensual voice. She continued with more of her theater, as she was in such a giddy mood.  We are huge fans of war movies, something Kate enjoys from her new culture.  

“Hey baby, you got girlfriend ‘Merica?  Me so horny.  Me love you long time.” she said, now back on her feet, and we howled laughing at her rendition of the classic funny scene from “Full Metal Jacket.”  Despite being an Asian woman, Kate is definitely not politically correct or highly sensitive at humor that might offend some others.

Hoping to turn the joke on her and muster another entrance into her exit, I grabbed a pump of lube and stroked my messy cock to see if I could revive it. I soon had to accept defeat and hope for another day.  Maybe someday I’ll manage to be up, physically, for a round two and reach previously unknown depths in her rectum.  Based on her reaction, when that day comes, maybe she will love two helpings of ass fucking almost as much as I will.

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13 replies
    • Alan Adventurous says:

      Thank you KingdomMan. Anal with Kate has been a marathon and not a sprint.

      Also, I only realized a couple days ago that you're back here posting. I don't managed to get on the site each day. I hope and pray all is going well with you these days. 🙂

    • Alan Adventurous says:

      Sorry KingdomMan, that was LovingMan that had the health issue/scare. I see he's back posting now. I got mixed up… Must be confused and already thinking about mischief with Kate tonight. LOL

  1. catholicguy says:

    Loved this story. This quote hit really close to home, “I also got vocal with some primal groaning, savoring the incredible feeling of pumping my cum into my lovely wife.”

    • Alan Adventurous says:

      Thank you. I'm a firm believer in letting yourself go and enjoying every bit of the bliss one has been blessed with.

  2. LovelyLonelyLady says:

    Hot story! I'm so glad that you show such patience as you experiment with anal, and your wife is willing and eager to try new things. She sounds like a wonderful lady. And I love it that she's not politically correct! We need more of that.

    • Alan Adventurous says:

      Thank you LLL. I hit the lottery with my bride to be sure. I tell her the same about me, every now and then. 🙂 Hard to believe two people that weren't particularly looking could find each other and be so perfect for each other.

      I also love her lack of political correctness. LOL

    • Alan Adventurous says:

      Well, if you're inclined to be a backdoor man like myself, hopefully you won't be a novice much longer. 🙂

      Nothing gets my pole standing up more promptly than when Kate gives me the greenlight for her asshole. Though I love everything in our sex life, anal sex is certainly my favorite. When she was first willing to give it a go, we tried to make it happen in short order and I just about had to peel her off the ceiling. Rarely is it tolerable to fully penetrate right out of the gate, so plan on patience to loosen and relax. All the best.

    • RevRoberto says:

      Latinas definitely have an understanding of anal but we haven’t talked about it in so long and then with kids running around the house, we rarely have that kind of alone time for patient experimentation. But I noticed my wife being a lot more ass-centric lately. She recently changed out all her underwear for thongs except when she is on her period. So she definitely has my wheels spinning again.

    • Alan Adventurous says:

      Rev, it wasn't until recent years that I heard how many Latina women are usually open to at least trying anal. Strangely enough, I ended up with a Filapina, whose culture does not often practice anal. While I definitely found my soulmate and she has broadened her horizons in the bedroom, the younger me would have probably been looking towards Latina women in my earlier days had I known.

      We have one daughter, almost two and we're really hoping to have one, if not two, more kids. Not sure how things will be impacted in the years ahead. If you're both willing to give it a go, work with fingers and buttplug play to ease into things, and when the opportunity finally presents itself perhaps you'll be ready for it. Nice to hear on the thongs, so maybe you'll be in luck. All the lingerie I buy Kate is always open crotch and I make sure it allows me to "dock the submarine" in "either port" shall we say. 🙂

    • Giants05 says:

      I agree this was a super hot story Rev. I can relate rev where my wife has become just like yours a lot more ass centric. Just like your wife mine went to all thongs and strings and I think it is so hot.

      Alan I agree anytime I get green light for anal I get so hard. Usually it's after she has an intense orgasm. And yes it's a marathon and not a sprint. This story yesterday certainly encouraged a nice Valentine's day ass fucking at my wife's request

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