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First Time Anal. First Time Cheating.

"My first time having anal sex with another woman."

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Well what can I say, I cheated on my wife with another woman. Why could I do something like this? Why should I, too? Well I have my own reasons, which I shall not get into on here. But I shall tell you how it began.

I had a wife-to-be and a son and daughter at the time and felt like everything was great; apart from one thing that is. Sex.

My wife isn't into trying new things or changing to different positions. So sex has been boring to say the least. I hadn't had sex for months and your hand can only do so much. I saw a pop-up for a sex website while looking for porn and gave it a try.

Now two months went by and no woman would reply to my messages, and I thought about giving it up until I got a friendly hello back from a woman called Sam. 

Now, Sam was two years older than me. I was thirty-one at the time. She lived alone in Edinburgh and was fun to chat, too. We exchanged lots of emails then text messages which turned into sexting. Then I asked about meeting her in person. She said yes and we arranged to meet at a pub in town. The day before, she messaged me to say she had to work late and couldn't make the pub. I said it was fine and we could do it another time. The next message took me by surprise. She messaged me and said, "Why don't you just come to mine? You won't be disappointed." How could I say no to that? 

I replied with shaking hands, "Yes," got her address and told my wife I was going fishing with a friend that night. I don't get out much so the wife bought it.

The next day went by uneventful until about 6 pm. I jumped in the shower and gave myself a good wash down, trimmed the hair, brushed my teeth good and made myself look good. At 9 pm I left the house with my fishing stuff and traveled into Edinburgh to sit for the few hours before Sam got home. I was very excited as this would be the first one in years that I could fuck. I dozzed off until my phone beeped to let know I have a message. It read, "I am home and awaiting your arrival. Don't be long, lover." I replied I was on my way and five minutes later I was at her flat door. I could hear a TV on and heard the faint sound of heels on a wooden floor. I knocked on the door and listened to the footsteps get closer until I heard the door getting unlocked and then opened. Sam stood there in the hall light wearing a very short skirt, tight white blouse with a few buttons undone to show off her great boobs, black stockings under her skirt, and finished off with black high-heels. We said hello to each other before she asked me to follow her into her bedroom.

I followed Sam into her bedroom which was her living room as well. She lived In a studio flat. Anyway, she looked sexy as hell and I loved walking behind her to watch her sexy bum wiggle. Once in the living room room/bedroom, she told me to sit on her bed which I did. She came over to me and kissed me hard on the lips before sticking her tongue into my mouth. This went on for a few minutes before she noticed the tent in my jeans.

Sam got on her knees in front of my and opened my jeans and took out my hard member from its tight confines of my jeans. She stroked me a few times and said what a nice cock I had. I told her it would look better with her lips around it. Sam smiled then took my throbbing member deep into her mouth, letting out a small moan as she did. She went to work on my cock, sucking hard and stroking me when she could. I was loving every minute of this, letting out gasps and moans as she went deeper on me. This went on for about twenty minutes before she told me she had a sore jaw. Just so you know, no woman had made me cum with her mouth, ever, which I told Sam. She did try her best but didn't get me there.  Sam apologised but I said it was great anyway and wanted to fuck her.

I stood Sam up in front of me and slowly stripped her naked. Until this point I never knew she never wore panties or that she was freshly shaved as well. I had to touch her folds which she loved, moaning loud as I felt how wet she was. I was fingering her with passion before she told me she needed cock and pushed me back onto her bed with my cock pointing to the sky.

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Sam mounted my and guided my pulsing cock to her wanton fuck hole. She slid down slowly, moaning while she did until I was deep inside her pussy. She was warm, wet, and very tight. Sam then started to bounce up and down on me slowly at first then picked up the pace until she was fucking me like a woman on a mission. Her mission was to cum. I started to play with her big tits, grabbing them and pinching her nipples softly before being told to pinch them hard. I put her nipples between my fingers and pinched hard. Sam let out a loud slow moan as she put one hand on her ass. At this point I did not know she liked anal until I realised she had a finger deep in her asshole as she got closer to cumming. I grabbed her hair and pulled her head back as she fucked the hell out of me and her ass with her finger. She screamed as she came hard. I forced her right down on my cock at this point to feel her pussy tighten and her whole body shake. She continued to moan loud until she came down from her blissfully state. 

Sam caught her breath and thanked me for making her cum. I asked her if she liked anal to which she replied, "No, I love anal!" At this point she raised herself up off my throbbing member. Feeling it twitch as she pointed it to her ass hole and sliding my cock into my very first ass. God damn, I said to her. It's very tight. She wiggled her bum, which I loved. I slowly pulled my cock to the entrance to her ass then slowly slid back into her. This went on for a while before I said fuck it! I grabbed her and threw her onto her bed, pulling my cock out of her ass.

Sam was shocked at my roughness but saw that I was on a mission. I got her onto her hands and knees before I parted her cheeks and slide my member deep into her ass again, slapping her cheeks as I did so. Sam told me to just take her so I did.

I started to slam my cock into her hard but slowly before I grabbed her hair again and started to ride her as hard and as fast as I could. Sam was moaning loudly, screaming stuff that I couldn't make out but I didn't care. I just wanted to cum which was getting closer with every thrust of my joy meat. 

Sam was cumming again, her pussy really creaming now as it ran down her legs and onto her bed covers. I was getting even closer to my own tipping point when she told me she was going to cum again, only a few minutes after the other one. 

I told her I was going to cum which sent her over the edge again. But this time I could feel her juices squirting out her pussy and hitting my balls as it did. Her ass really tightened at this and I couldn't hold on any more.

I thrust deep into her one final time, grabbing her hips tight as wave after wave of spunk emptied inside her well used ass. We fell onto the bed in a heap of sweaty cum covered mess, which was just a pure joy. I lay on her, with my cock deflating inside her asshole. 

After what seemed like ages, I pulled my limp cock out her ass and lay on my back and just smiled to myself, saying in my head that was one tick off my ' to do before I die' list.

We chatted for a while before I realised it was three in the morning and I better make my way home. I got dressed seeing that Sam thought I was staying the night. I told her I couldn't as I had to do something. She never asked what. We kissed again. Then I left with a big smile on my face. 

The travel home was quiet and all I could think of was how good her ass felt. I got home about 3.30 am, put my fishing stuff in the living room before going for a pee and washing my cock clean. It was nearly 4 when I got to bed still thinking about the fine ass I had cum into. I dozed off thinking to myself that this sex site was a gold mine if I could get more women to chat to.

I have a few more true stories to tell you all about like the older woman who fucked the life out if me to the best pussy I have ever tasted. But those are stories for another time. 

 

 

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Written by Sexmadscotsman
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