Long time lurker, first time poster. Skip to the honeymoon part for the point of the story and the more detail.
We have been together for six and a half years now, and just recently married. She is 5'4", brunette, lusciously curvy with an ass to die for. I am 5'10" average build, broad shoulders, nothing too wild. We began our relationship her as a virgin with very little experience, and myself who had sex about three times with a past girlfriend.
Throughout the start of our relationship, we began to slowly explore our sexual boundaries. It started as usual with groping, teasing, leading to oral and eventually we did the dirty. This opened up a whole new side of both of us as we were constantly horny and in need of each other. Three, four and five times a day and we had to stop just because we were so sore. We talked about each others fantasies, and mine being the standard for a guy – anal, facial, swallow, etc.; and hers being on the conservative side – back seat of the car, different places in the house, the most elaborate of wanting to be in a tent outside. We started to slowly satisfy each others desires albeit, rather clumsy.
The time came for my fantasy of anal to be tested, and while she was reserved about it, we agreed to try it in the shower "just in case". Nothing could deter me at this point and I was determined to have this be a successful attempt. Boy, was I wrong.
We entered the shower and began slowly kissing and fondling each other trying to get in the right mind set. Finally, the moment presented itself. I grabbed the lube, lathered up my cock and her asshole as she bent forward and allowed the warm shower water to run over and down her back. Slowly I slipped the head of my cock into the opening of her ass. This glorious moment I will remember forever, and in one swift movement I eased it passed the tightened muscle and watched it swallow my cock whole. I made sure she was okay at this point as she seemed uncomfortable, but she motioned to keep going in what I assume were hopes of it becoming satisfying. Slowly I worked back and forth, all the while paying attention to her body. I would hit certain spots and make her back arch, or could feel her tighten her muscles. Eventually it took its toll on her and she insisted we stop. I was in ecstasy even though I had the balls as blue as the deepest ocean.
From this event, she said that she did not like anal as much as she had hoped and I thought for sure that my new found fetish was all but squashed. Occasionally, when we would spoon, I would rub the head of my cock on her asshole and she would push back slightly to create some pressure on my member. This usually sent me to the edge and I could not contain myself, and on more then one occasion we had to change the bed sheets. Her constant teasing was probably because she knew what it did for me, but it also kept me with an insatiable appetite to have her ass once more.
Throughout the next couple years and eventually through our engagement, we tried a couple more times to no avail – maybe it wasn't enough lube, or the wrong angle, or I got too excited and went half mast after emptying a load on her ass cheeks. But then she received this gift from a friend that is a glass blown ring holder for when she takes a shower or what not. Just a novelty item if you ask me, but a nice decoration none-the-less. In my fruitless attempts at planting the seed of trying anal again, I mentioned that it looked like a butt plug. Surprisingly enough, she took the hint and in the most seductive way possible she said, "Why don't we get one"? I felt like I just had hot adrenaline pumped through my veins as I turned beet red, and my heart was racing. I flew through the house to grab my iPad and started browsing the interwebs for butt plugs of all kinds. She eventually came and sat next to me and we perused the online shopping centers looking for the right one. She was unabashedly excited about which one to get, and I couldn't help but wonder if she had researched this herself. We finally picked one and it arrived within a few days.
The first night we tried using this was an utter failure and it ended with it hurting too bad for us to continue. After some discussion of what I shouldn't do, we attempted this again and had great success. With the toy lodged in her ass, I began to satisfy her pussy until she came with the most powerful orgasm on record. Shortly followed thereafter with me dousing her in ropes of my cum all over her stomach and chest. I rolled off her and laid panting next to her paralyzed body as I heard the "schlick" of the toy find its way out of her relaxing asshole. This was the start to greatness, and I knew it.
*******Honeymoon part***********
We had just gotten married and were on our way to tropical paradise, and I knew I was in for some amazing sex all week long. I could see it in her eyes, and well she told me flat out. We arrived and the first night ended with a bubble bath, champagne, room service, and us consummating our marriage in the most vanilla way possible. It was the passion and love that made that one of the best sexual experiences either of us have had to date. That was thankfully the only night that we had plain old sex.
The following night we settled down after a nice hot shower together to wash away the sun lotion and chlorine from our skin. Watching t.v. laying in bed, reading our books, kissing every so often, etc. Eventually I was starting to feel the tingle in my balls and I began to realize the sexual urges start to well up inside me. I rolled over and began to slowly rub her clit from the outside of her panties. Noticing she was already a little hot and wet (thank you some random bridal fiction books full of descriptive sex) and starting to close her eyes as she was losing interest in her book, I slid my hand under the cotton of her PINK panties and began to feel the smooth, freshly shaven mound leading down to her slit. I made a finger slide into her with ease and her moan in pleasure as she moved her book to the side of her. I started to kiss her lips before moving to her neck, stopping briefly to take in her smell and moving to her breasts. Spending a little attention at each nipple while maintaining a soft touch inside her velvety vagina. I could feel that rough spot at the front of her pussy start to engorge itself as I moved my tongue to her belly button. Her breath became faint in between deep gasps as though I was controlling her lungs with each push of my finger into her. I re-positioned myself so that I could lay my warm tongue across her clit as I kept moving my finger in and out. I twisted my wrist a little and used my ring finger to massage her asshole and as I increased the pressure I could feel her muscles tightening and relaxing.
After several minutes of getting her all hot and bothered she couldn't take anymore and I knew she needed my cock. She rolled over and lay on her stomach, her favorite position. I reached for the bottle of lube and set it next to us before I started to guide the head of my dick into her wet and awaiting pussy lips. Finally breaking the threshold I here a loud sigh of relief from my wife and I start to slide in and out of her. Pumping my dick into her and feeling her ass cushion every thrust was making me harder and harder with each push. Eventually I see her hand start to move slowly down her side heading for mine which was holding her ass cheek. She grabs my hand and moves it with intention toward her ass hole. I know exactly what she wants.
I grab the lube and put some drops right on her inviting pink star, rubbing it slowly around while listening to her breath deepen. After it feels adequately moistened, I apply pressure with my thumb to spread her hole open as it envelopes my finger with ease. Slowly I start to massage her ass with my thumb alternatively as I am thrusting my cock in her pussy. This continues for several minutes before she takes an initiative and rolls onto her side. I have to pull out from the movement, and before I can align back to her pussy with my dick, she turns her head and gives me that look. The same one from when I had halfheartedly mentioned the butt plug ring holder, and I knew this was going to be memorable. She reached across her body and grabbed a handful of her ass cheek and pulled. Spreading her ass open and allowing me the clearance to place the tip of my throbbing cock at the opening to her asshole. From all the lube I had used in teasing her ass, I slid right through with little resistance. Her body twitched, and her mouth formed that "Oh my God, that feels good" look. I pushed all the way in and buried my cock as far as it would reach before slowly pulling it back so the head was right at her opening. Several times I did this before placing a hand between her legs and working a finger into her pussy. I began to pick up the pace now as I was fully accepted into her ass for the first time since the shower, and it was everything I had hoped it would be. The sensation was worlds apart from what it had been in all those failed attempts behind us. We both were in sync now, and I could feel her orgasm building – mine was not far behind. I continued to pick up the pace of both my cock, and finger before she put a hand on my stomach and tried to grab for something so she could pull me in deeper. I knew I was only a few thrusts away from flipping her world upside down. Her breath was shorter, heavier, more deliberate until her body began to convulse in a epic fight for survival to withstand this orgasm that has now consumed her. Her involuntary movement applied the right amount of pressure to me and I knew it was coming. I said as deliberately as I could, "I am going to come inside you". She nodded, and I let loose. Ropes of cum filling her asshole in one of my biggest orgasms all while she hasn't stopped having hers. Finally after a minute long climax for the both of us, I slide out of her and fall over to the other side of the bed. Unable to move my body to get her a towel to clean up. She slowly gets up and walks to get a shower and I see my cum leaking from her ass and dripping down her leg.
Best night of the honeymoon by far.
Source: reddit.com/r/gonewildstories/comments/3rs79f/mf_honeymoon_anal_with_long_back_story
Great story, good ass play. Keep writing!