Double Your Pleasure Ch. 01

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Mature lady experiences anal sex twice consecutively...
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Part 1 of the 2 part series

Updated 06/08/2023
Created 08/04/2017
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After numerous discussions over the years, my husband and I finally decided to take the plunge to satisfy one of our mutual fantasies. That being for hubbie to watch and photograph someone ass-fucking yours truly and for me to experience anal sex twice consecutively.

Before I continue with my story I should clarify a few things. When it comes to cocks, bigger isn't always better in spite of what many may think. Hubbie's cock is a good 8 inches when fully erect, but unfortunately a cock that long can be problematic when having vaginal intercourse. Quite often it would, or does, bang against my uterus, which can be painful and ruin a good sex session. As often as we tried, it hitting against my uterus would happen in spite of our best efforts to avoid it. So much so that I very often found myself avoiding intercourse.

After years of frustration, hubbie suggested we substitute anal intercourse for vaginal. By then I figured nothing ventured, nothing gained. The first few times were uncomfortable for yours truly, but the more we did it anally, the more I enjoyed it. Eventually it opened up a whole new world for me in many ways. Now any sex we have that ends with intercourse is almost always anal. I enjoy anal so much so that I often orgasm when hubbie fucks me in the ass. Vaginal intercourse is rare for us now. Between oral (which we always enjoy) and anal, our sex life has taken a turn for the better.

Which brings me back to my story. And so you'll know, we're both mature adults. Of which has a lot to do with our desire to fulfill some of our fantasies that we never thought of doing when younger.

With that said, the fulfilling of our above mentioned fantasy took place rather easily when one of our mutual friends agreed to the proposition and who is a couple years younger than us.

Once we got together at our home, and after a few drinks and some small talk, we decided it was time to get down to the "dirty deed" so to say. We relocated to the bedroom where we quickly undressed. Albeit somewhat nervously on my part.

Once naked it was obvious both hubbie and our friend David were already "excited" as both their cocks were all but fully erect. Both were quite enlarged, although not fully hard. Think of an engorged cock that's still somewhat limp in that both their swollen penises hung down between their legs instead of straight out upright.

Plus there was a distinct difference between hubbie and David's cocks. Hubbie's, as previously mentioned is long, a good 8 inches when fully erect, slender with a big cockhead...plus he's not circumcised. David isn't circumcised either, but his cock is shorter than hubbie's by a few inches. The big difference is what David's cock lacked in length it made up for in girth. Maybe twice as large around as hubbie's. Very fat, and it was most definitely going to be the fattest cock to do me in the ass.

I should also mention that David's cockhead is smaller and cone shaped, which unlike hubbie's large cockhead would be able to penetrate one's asshole more easily. It actually looked like it was made for anal. Pointed tip and it increased in girth down along the shaft to the base where it is larger in diameter by a third than just below the cockhead. If I was going to design an anal dildo it would mimic David's cock exactly. Bottom line, I couldn't have asked for two distinctly different cocks to do me in the ass and was looking forward to how David's would feel.

I was so fascinated by David's fat cock that I asked him if I could suck it. Never had such a short fat cock in my mouth. Which by the way is my second favorite thing to do...suck cock.

"Sure" he said..."I've been fantasizing about you sucking my cock for as long as I've known you. Please do if Walter doesn't mind."

After looking at hubbie who nodded his approval I got down on my knees and took David's cock in my mouth. Only the cockhead at first after I gently pushed back the foreskin to expose it, which I then gently sucked and tongued until his cock became rock hard. Then I began mouth fucking it and found with a bit of effort I could easily take all of it in my mouth because of its short length. Although it was quite a mouthful girth wise.

After a few minutes of steady mouth-fucking I sensed David was enjoying it too much by his muted moans and the pressure he was applying to the back of my head with his hands as I took it deep in my mouth. Since he seemed about ready to cum I released him and explained I wanted to save his cumload for my ass. I didn't want it deposited in my mouth or on my face. At least not now. Although disappointed he fully understood, but did say that hopefully there would be a time where I would suck his cock from start to finish. Which I agreed to do since he was nice enough to help us fulfill our fantasy.

I then positioned myself on the bed on my knees and elbows. With my legs spread and my asshole fully exposed both hubbie and David began taking turns licking & tonguing it. From the sounds they were making it was easy to surmise they were both enjoying my asshole as much as I was being pleasured from them licking and tonguing it.

Once my asshole was well lubricated from saliva there was a short pause before I felt hubbie's cockhead pushing against and then entering my asshole. Once his cockhead was fully inserted he began humping ever so slowly while penetrating and inch or so deeper on each forward thrust until nearly all 8 inches of his long cock was buried in my ass. Then he proceeded to fuck me with a steady in & out motion and long deep strokes. It didn't take long before I felt his cock get extra hard and begin to throb ever so slightly. A sure sign he's about to cum.

While this was happening I could see David over to the side intently man-handling his cock while watching hubbie pumping his in & out of my asshole. The look on David's face was amazing, it was like he was high on grass...very glassy-eyed like he was in a daze.

He explained afterwards it was the first time he ever watched someone getting ass-fucked in person. "It was such a huge turn-on...more so than I ever expected. I had all I could do to not cum while watching Walter's long cock fucking your luscious asshole. Maybe one day I could watch Walter do my wife in the ass."

Side note; little did any of us know at the time it would actually happen, and sooner than we thought.

Next thing I knew hubbie's grip on my butt cheeks tightened as he shoved his cock in so deep his balls slapped against my pussy. Just when he did a big stream of hot cum exploded deep in my ass. Not one cum stream, but multiple ones that were perfectly timed with my own orgasm that resulted in a number of cunt farts.

David with cock in-hand blurted out..."Wow! I never heard a cunt make noises like that when being ass-fucked. You must really be enjoying it Lacey!"

After hubbie fully drained his hot load in me he told David to get ready so he could shove his cock in my ass before any of his cum seeped out. With that said, hubbie withdrew his now semi-limp dick and no sooner than he did David took his place and shoved his fat cock in my now well lubricated asshole.

After being fucked by hubbie's long but slender cock, David's exceptionally fat cock felt truly awesome because of the difference in girth. Especially when he fully inserted it and the wide base of his cock would stretch my sphincter muscles to the limit. A tad painful at first, but in an enjoyable way. And no way could I have taken David's cock before hubbie...just too fat to have been the first to do me in the ass between the two.

Unfortunately David became so aroused from watching hubbie ass-fucking me that it didn't take long before he was ready to cum. Unlike hubbie with a steady slow rhythm, David was more like a jack hammer pounding away against my ass. Like a teenager getting his first piece of ass. Or else he was just overly excited about being able to fuck my "luscious" asshole as he called it. Either way...hubbie had to tell him more than once to slow down so he could get some pictures of his cock embedded in my asshole. But I wasn't complaining, his fat cock felt soooo good slamming in & out of my asshole.

All of a sudden David let out a loud moan and the next thing I knew his cock was gushing loads of hot cum inside me. It felt like a popped bottle of champagne. Biggest cumload I ever took in my ass. Seemed simply huge in terms of the volume of cum that erupted from his cock.

I didn't know at the time, but his cumloads are usually always big. I just assumed it was a bigger load than normal from being overly aroused and/or he hadn't ejaculated in a while. Little did I know David is one of those true cum masters, and on any given day would put most men to shame with the amount of cum he routinely generates.

Once fully drained David withdrew his shrinking cock from my ass and then I heard hubbie say he needed to get a photo of the huge anal gape I had. Claims he never saw me with such a big gape, which was from either being double ass-fucked, or most likely from David's insanely fat cock. Then as the gape closed they both stood back to watch their collective cumloads seep out of my asshole. Once it started the cum oozed out for what seemed like 10 minutes. All of which formed a big puddle of semen on the bed sheet as it steadily flowed out and dripped down and off my pussy lips.

While we were cleaning up afterwards, David mentioned he couldn't be more pleased that we asked him to be the one to help make our fantasy a reality. He then explained that he and his wife rarely ever have anal sex because of his cock being as fat as it is and his wife having a very tight asshole. The two were just not compatible for enjoyable anal sex, which as a result they don't do often. Much to their displeasure.

So it goes without saying, that fucking me in the ass was extremely pleasurable for him since my asshole accommodated his fat cock so easily. I explained that as often as Walter ass-fucks me it's not surprising that I could. In ending he said he hoped it wouldn't be his last.

The End.

PS...Trust me when I say, while a good ass-fucking feels wonderful...a double ass-fucking is simply terrific. No way to describe it, especially when the second cock is significantly fatter than the first. David's fat cock definitely "kicked it up a notch." It was mind blowing. Anyone that enjoys being fucked in the ass should most definitely entertain doing a double...of which this first one won't be my last.

PSS...hubbie got some terrific pics of David ass-fucking me, which we view often. Sometimes together while we mutually masturbate, or hubbie does while I suck his cock. David also has a set on his computer, which he often masturbates to when viewing them.

Next chapter from will be when I suck David's cock till fruitation. Then another detailing the time David's wife joins us for a terrific foursome.

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16 Comments
Kicker73Kicker735 months ago

Excellent rewrite!

Marklynda2Marklynda28 months ago

Interesting that she doesn't want a shorter dick to truly experience enjoyable vaginal sex. A great start to what promises to be a well thought out and written story. I look forward to reading the next chapter. As this is my first foray into your writing and the first story you posted here I have added you to my favorites list. I appreciate your and your Muse's imagination (memories?) and abilities to bring it to your story. Thank you for sharing your vision and talents.

AnonymousAnonymousabout 1 year ago

Taking this as a true story, the writer advises that a long penis can cause pain if the penis can reach a depth of her uterus. I fear I could have done this to one woman, but she loved the oral I gave her. I thought if the writer liked oral, she wouls tell us about that. As it is, she may tell us about threesome with her being done by both men simultaneously.

chytownchytownover 3 years ago
A HOT AZZ Read****

Thanks for sharing.

AnonymousAnonymousover 4 years ago
Years ago......

Starting about 17 years ago I had the good fortune to be invited to be the 3rd wheel in a long term threesome with my work buddy and his girlfriend. She was another mature lady who loved ass fucking and like the 2 guys in this story, he was the smaller of the 2 of us guys so usually he had her backside first, but not always. She also loved double vaginal sex, now that was one tight fit but VERY pleasurable for all.

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