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Introduction:

This is the continuation of my story on how I come to enjoy anal play
This is a continuation from my childhood experiences that lead me to enjoying anal play. Please provide votes and comments to let me know how you enjoy my story.

Fast Forward ------->

Now I'm 20 years old, I've been in the army for the last 2 years and I'm stationed overseas. Since high school, I've had probably another 20-25 sexual partners, but none of them really interested in anal play. Sure, some were kinkier than the others, but none as kinky as Jenny when it came to anal. I did have my first proposition from a gay guy, but it never went anywhere. I wasn't attracted to him and I definitely enjoyed pussy and breasts too much. Breasts not so much, but the pussy, I couldn't do without it. By this time, I'd become a self-proclaimed coochie connoisseur. I enjoyed eating it as much as I did fucking it and couldn't imagine having sex without it (unless it was with myself).

This is where I met my 1st wife. Karen was 19 years old and an Army brat. We were dating for about 4 months when her Dad told her that he was about to retire in three months and they were moving back to the states. Sex with Karen was good. Actually, it was great. Karen was just as kinky as Jenny and was open to trying about anything. Karen was even open to using a finger or two on me when she would give me a blow job. With Karen is when I first experimented with toys. She was a highly sexed person and it seemed like she could never get enough.

One night we were in a 69 and I was going to town on her. However, tonight I was also using the vibrator on her at the same time. The vibrator was a bit smaller than me, about 1 1/2 inches and made with the realistic looking jell type surface (she didn't like the hard ones). She had come fairly quickly in a pretty intense orgasm and couldn't take any more of my tongue or the toy so she took the toy away from me and told me to lay back and enjoy the show. She was still laying on top of me giving me a pretty good blow job when she turned on the toy and started rubbing it around my shaft and balls. All I could do was lay my head back and enjoy my awesome surroundings. There's not too many places in my mind that are better than having a cleanly shaven pussy dripping on your face while having your dick sucked and a vibrator slid all over your shaft and balls.

She continued to work her magic on me when the vibrator slide down to the underside of my balls. As I said before, she's put a finger in my ass before but never anything other than that. I started to get a bit excited and opened my legs up a bit more for her to explore at will. Generally Karen's blow jobs aren't very sloppy, but this time she started letting saliva drip all over the place. Again, giving me that awesome feeling of totally slicked up groin with several types of stimulation happening all at the same time. She then moved it down to my ass and started rubbing the length of it against it. Man what an awesome feeling. I've had fingers in my ass as well as a few other small things, but never anything that vibrated. I opened my legs up further to give her more room to rub the vibrator around and that's when she took the hint.

She slowly stood it up on end and gently started pushing it in. Up to this point, I've never had something this size in my ass. Technically 2 fingers side by side is about the same width, but they're not completely round. It took her a bit of persuasion to get it in, but once she did it felt incredible. Like I said, it was a bit bigger than anything I'd had before so there was again that familiar stretch pressure that teetered between pleasure and pain, but lifting my legs up and spreading a bit more was all it took for pressure to become pure pleasure. She took her time sliding in the vibrator, which was much appreciated, and I could feel that the head of the vibrator was about in. After the head popped past my sphincter I had gasped. I'd never felt that full before. When it was about 5 inches in that's when she started working it. I couldn't believe how good it felt to have her mouth going up and down on my cock while she was working the vibrator in and out of my ass. I was in absolute heaven. The ribs on the vibrator were tickling the nerves in my ass every time she pulled it out or pushed it in. It felt so good I had asked her to stop sucking me so tediously so that I could prolong the feeling. She kept stroking the vibrator in and out and picked up the pace a bit on it.

We had been in this position for a while and she felt the need to re-adjusted herself on top of me. This changed the angle at which she was now pounding this miracle tool into my ass. This is when I discovered for the first time about the prostate massage. I didn't know what it was at the time, all I knew is that it was like pushing the holy-fucking-shit button. After she found my button, it didn't take me long at all for me to drain everything I had all over the place. I laid there for a few minutes in the position I was in, legs up and head back before she slid the vibrator out of my ass. I dropped my legs and simply laid there -- couldn't move.

That was the first time. This happened several times after that with the same toy but in a various array of different places and positions. The funny thing is that she seemed to enjoy it as much as I did. I don't know if it was love or lust, but I asked her shortly there after to marry me. I knew I had to keep this one around. Eventually, the toys got a bit bigger, but never much bigger than I was and we both enjoyed them equally as much. When she was at work and I was feeling frisky alone I'd have a self session myself. This lasted about as long as the marriage -- 4 years.

A few months after I'd gotten divorced I started getting "out into the field" again. I had had sex with a few women, but none of them seemed interested in any sort of anal play -- mine or theirs. I'd succumbed to the fact that most women didn't like anal play and I blame that mainly on society. In society, anal sex is often though of as weird or gross so a large majority of women (and almost all men) avoid it like the plague.

But this didn't stop me. I still had bouts of playing with myself anally on occasions and I even went and bought myself a couple toys to aid in the fun. If there's one thing that my ex had taught me, it's that toys can be much more pleasurable than fingers. Especially ones that vibrate.

Shortly after the divorce, I went and bought a toy very similar to the one that I had used before with her however this one was a bit longer. I found that I definitely enjoyed a bit of length so that I could hit my prostate a bit easier and still had a fair amount of toy to hang on to. It was always easy to conceal why I had a toy. The general story was that the ex had left it and I had just never gotten rid of it. On occasions, the women I was having sex with wanted it used on them. I'd always take special care to clean them after using them each time so they were always extra clean.

One of the women I was fucking expressed that she was interested in a bigger toy, one that was slightly bigger than my cock was. Now, my dick has a fair girth of about 1 3/4 inches so off to the toy store we went. The one that Mandy had picked out was just slightly larger than I was but still under the 2 inches mark. The entire time we were shopping, I was just as sexually charged as she was. Mandy thought my excitement was all about the fact that she was getting a bigger toy and that I'd get a chance to use it on her when we got to my house, but I was fantasizing about using it on myself just as much as she was fantasizing on me using it on her.

Later on when we got back to my house we were both pretty much stripped naked less than 10 steps from the front door. The new vibrator was packaged in one of those child proof packages so I headed directly for the kitchen to get a pair of scissors to cut the package open. As soon as I got it out of the package, I washed it up real quick with some dish soap and started digging through drawers for some double A batteries. The toy was now out of the package, cleaned, powered and ready for use.

She stood there looking over my shoulder the entire time I was getting it ready so she was already extremely wet by time I turned it on the first time. As soon as it was on, I turned to her and started rubbing it between her legs as we kissed. I backed her up to where she was leaning back against the kitchen table. We broke our kiss and she leaned back and spread her legs a bit more allowing me better access to her pussy. I moved down to her pert nipples with my mouth and began my alternating nipple suck and nibble technique while still rubbing the vibrator on her clit and pussy lips. By this time, she was so wet and ready that the vibrator was slick with an ample amount of lube so I laid her back further and placed the electrified tool at the opening of her pussy.

When we first got together, she commented several times on the stretch that my cock provided her. This was a bit bigger than me so I was excited to see what kind of sensation Mandy would be feeling from this. I started to associate the exact same thoughts with the way that I felt with my first experience with a toy in my ass to the fingers I'd had. It was an extraordinary feeling and I assumed it'd be the same for her.

I slowly started inserting the head of the faux penis in her pussy and I must say the sight was incredible. Her clit was engorged and throbbing as a result of all of the rubbing I'd been doing to this point and her luscious pussy lips were glistening from her own juices and being parting this toy had given me the biggest hard on I'd felt in a while. As I slowly pushed in the toy, a gasp had escaped from her mouth. She quick grabbed my hand to stop me from pushing any further. Mandy was getting used to the sensation of the extra stretch. I was mesmerized by the sight that was in front of me and couldn't help but to lean down to give a couple of tongue flicks to her needy clit.

A couple flicks of the tongue and she was pulling my hand to push deeper into her. At first I worked it nice and slow, but as the pace began to pick up so did her breathing. Within 30 seconds I had her writhing all over the kitchen table in a massive orgasm. I thought to myself that I had to have this thing.

After the display in the kitchen, we moved into my bedroom. I had gotten the old toy out of the night stand, handed it to her, and laid on my back on the bed. I told her to get on top of me in a 69, I wanted to fuck her again with the toy as she held her leaking pussy over my face. She looked at me with a sort of a confused look while holding the vibrator and asked me what she was to do with it. I told her that I loved to get a blow job while having a vibrator rubbed all around. I was hoping she'd take the hint and use it in my ass to prime me for the new one later -- with or without her.

She did as she was told and crawled on top of me. The sight of her pink folds above my face mixed with the scent of an excited pussy was nothing short of exhilerating. I took my time to lick and plant little kisses all around her pussy as she put her mouth around my now engorged cock. She had turned on the vibrator and began rubbing mainly around my shaft. Even though this felt good, it wasn't where I wanted it. I wanted it around my balls, in the creases between my balls and thighs, and in my ass. I had to move one of my hands down to gently show her that the shaft was not the place for her mouth AND a vibrator.

She gradually took the hint and started moving the vibrator all around. When she got to the underside of my balls, I lifted my knees and spread my legs apart and made sure that I gave a couple loud moans into her pussy. I knew that she'd both hear and feel the moans on her pussy and would hopefully take the hint. The closer she got to my asshole, the more I moaned until she held the tip of the vibrator on my asshole. By this point, my feet were up in the air and my legs were spread pretty much as far as they would go.

This must have excited her as well because the more she rubbed around my rosebud, the more I moaned and the more she ground her pussy into my face. At this point, she was wet to the point where her juices were running down the side of my face creating little streams that joined in the back of my neck and dripped off onto the bed.

With the other vibrator in hand, I began to rub all around her pussy to get it nice and wet again. As I was rubbing her pussy, I'd create a long stroke the crack of her ass to ensure I was wetting the whole area, including her rosebud. I started concentrating more on her ass and as I did she was getting more daring with her vibrator on mine. She slowly started inserting it into me. At this point, she all but ignored the head of my dick and was now licking and sucking on my balls while slowly running her toy in and out of my ass. All I could do was lay my head back and offer moans of approval.

I slowly applied pressure to the toy in my hand and every time I would push down she would moan and rub her pussy into my chin. Mandy was now ramming the toy in and out of my ass while sucking on my balls and licking the creases between my balls and thighs. This wasn't going to make me cum, but the feeling was exquisite. Then she pulled the vibrator out of my ass and began to sit up.

Man, I was disappointed to say the least! What the hell was she doing? She got up and went to the bathroom and closed the door. There I lie. On my back, legs still stretched up and out, holding the big vibrator and she runs to the bathroom. I asked what she was doing and gave me a "hold on". Ok, I thought.

I heard the toilet go and then the sink run. When she came back out she jumped on the bed and hit the same position that we were in before. This time she grabbed the big vibrator and gave me the one that she was using earlier. "What the hell?" I thought. Then It hit me, she had gone to the bathroom to make sure she was empty and to clean up the old vibrator so she could swap with me! Her ass was now soapy fresh, as was the vibrator, and she was once again sucking on my cock.

Mandy placed the head of the big vibrator at the opening of my ass and began to push slowly. The difference in vibrators wasn't that great when you held them side by side, but let me tell you that a small difference in size makes a huge difference in feeling! When she finally got the head of the big vibrator in my ass, I felt just as she did when it was in her pussy and I quickly grabbed her hand to just hold it there for a bit. What a stretch it was giving me for only about another quarter of an inch.

With the smaller toy in hand, I began the whole routine of using her own juices to lube up the other vibrator. Since she had cleaned up a bit, it took a couple of dips into her pussy to get it thoroughly wet, but once again I was applying pressure to the toy at the entry of her ass. This time, it slipped in fairly easily. We hadn't talked about anal sex, so I wasn't sure it was something that she had done much, or if at all but my guess was that since this slid in fairly easily she wasn't a complete stranger to the idea. Once the tip was in, I left it there for a bit to allow her to become accustomed to it.

Now she was starting to slide the monster into my ass slowly. As she did, she continued to lick all over and on occasions take my cock into her mouth. Again, not a bad place to be in life. A vibrator in your ass while a woman blows you and lookup up at a juicy wet pussy with a vibrator sticking out of her ass. Slightly more mind blowing than what I experienced before. The sensations that I was feeling was about the same -- warm mouth on my cock, a vibrating toy in my ass providing me a bit of a stretch -- but to now be not only pleasuring a pussy with nose/tongue/chin, but to see her taking one in the ass too was a bit too much for my mind to handle.

I continued to push the toy in to her ass slowly and went back to sucking on her pussy with a vengeance. I needed something to keep my mind off of the incredible pleasure she was providing me so that I didn't blow right then and there. As I started probing a bit faster she finally lifted her mouth of my cock to let me know that she was going to cum and wanted me to cum with her. That's all it took! I pounded her ass harder and ate pussy like I've never ate before. She pounded my harder as well and started swallowing as much of my cock that she could. The sensation of my cock against the back of her throat, her pounding the monster in my ass and grinding her pussy in my face was all I could take. I finally succumbed to everything and exploded in her mouth. It must have had the same effect on her because shortly after I felt a flood of juices hit my face.

We removed the toys from our asses and both just laid there on the bed. Spent. There wasn't even any talk. We were both simply relishing in our ecstasy. I had found my new anal buddy.

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This is my first attempt at writing so please vote for my story to let me know how I'm doing. If you vote negatively, please add a comment to let me know how I can improve. If you really like it, comments on how awesome it was will be appreciated as well.
2 comments

anonymous readerReport

2012-05-14 10:23:52
Dude, hell of a story. I thought I was reading my own life story. I guess there are others grew up that way. I also grew up with my dad's porn collection...got into anal stimulation..etc. Except I did the dildos earlier in life. Let your girl work up to fisting you if not already........nothing like it in the world. Just when you think you can't have stronger orgasms.....KaaaBoom! Will give you a part 3 to look forward to. Nicely written and detailed.

anonymous readerReport

2012-03-11 21:10:43
I never really thought about anal play before but this story has me willing to try something new. Please make the next one soon. Very good stories.

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