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Introduction:

My first adventure with a older woman
This story is all about Evelyn, and what happened when I was 18. Evelyn had chartered the boat I worked on for a day with her family which consisted of her 7 year old son and her Mum (she was divorced). Evelyn was probably 37/38 if my memory serves me right and what you would definitely call a Milf. Tall, blonde, a great set of boobs and the most perfect body (I guess you would say she was curvy, but not fat in any way).

We had a great day on the boat and Evelyn was certainly very friendly, as the day wore on and the wine continued to flow for the guests she definitely started to ask more probing and personal questions. At this point I just brushed it off as friendly banter, little did I know……..

That evening I dropped them back at the quay in town said my goodbyes and thought that would be that. Evelyn was last to get off the boat and as she did she thanked me for a wonderful day and said I should join them the following night as it would be there last night and she wanted to buy me dinner to say thanks.

I rocked up the next night and was immediately blown away, Evelyn looked stunning in a very sexy clingy summer dress that showed off her amazing rack. Dinner with her family was nice, I kept taking cheeky glances of her boobs which I am pretty sure her mother clocked several times. After dinner her Mum said she would take her son back to the hotel and that we should continue on drinking, I certainly wasn’t going to say no and Evelyn was more than happy to accept her Mum’s offer to babysit.

Evelyn and I headed to a local bar and had a great time drinking and dancing, as the booze started to hit us both our dancing became more and more raunchy with lots of grinding. She had an amazing ass to go with her fantastic rack and I am pretty sure she could feel how hard she was making me. It was August and very hot, between the dancing and the grinding we both started to build up a bit of a sweat, that’s when Evelyn suggested we go skinny dipping to cool down!

We headed along the beach away from town hand in hand laughing and giggling like a couple of kids. No sooner had we found a good spot Evelyn was already half naked. I can still remember now the sight as she whipped her dress off to reveal a matching pink bra and tong set. And I am hard now thinking about the first time I saw her boobs, they were probably a good D or DD cup, lovely big pink nipples and hardly any sag which was pretty impressive.

Evelyn ran into the water and I followed right behind her. She swam over to me and wrapped her arms round my neck and kissed me hard. She had lovely full lips and her tongue was darting all round my mouth. It was shallow enough that I could just about stand, and as we continued to make out she wrapped her legs round my waist. Evelyn started to grind against my now rock solid cock as we got more and more passionate. Then without warning she grabbed my cock and guided it straight into her warm, tight pussy. Despite being in the water she was so wet that after a little bit of adjusting she was able to start to ride up and down my long hard cock whilst I sucked on her nipples making sure that each one got its fair share of attention.

This continued for a good 5 minutes or so until Evelyn said “I need more, let’s go back to your place so you can fuck me properly”. Needless to say I was out of the water and dressed in seconds. Evelyn put her bra and dress back on but stuffed her pink thong into my back pocket.

Back at my apartment we headed straight for the shower, we were both covered in salt and sand. Once in the shower we picked up where we had left off, kissing and groping each other like a couple of teenagers. I grabbed the soap and started to lather her up paying special attention to her breasts, amazing arse and pussy.

It was then my turn and once Evelyn had finished washing me off she got down on her knees and slowly took my cock in her mouth. I am a massive fan of blow jobs and Evelyn certainly didn’t disappoint. She definitely knew her way around a cock and mixed up taking me as far as she could in her mouth with swirling her tongue round the tip of my cock whilst one had ran up and down my shaft with a twisting motion and the other played with my balls.

Shower over we jumped out and immediately I had Evelyn bent over the sink. The feeling of entering her pussy for the second time that night was as good if not better than the first time. Her lips gripped my shaft as I picked the rhythm up and really went for it. We locked eyes in the mirror as I pulled back on her hair.

As we both started to get a bit tired I flipped Evelyn round and lifted her up onto the counter by the sink. I then started to kiss her from her neck down to her boobs, playing gently with her nipples, down her stomach to the inside of her thighs. I teased her by kissing all around her pussy but not going anywhere near it. By this point she was begging me to lick her pussy and eventually she couldn’t take it any longer and grabbed my hair and forced my face into her pussy.

Now up until this point I had never been with someone much older than me, let alone someone who had given birth. I had always imagined that after child birth things wouldn’t be/look the same down there (Please don’t judge me!). How wrong was I, Evelyn’s pussy was a thing of beauty. She was completely shaved apart from a small strip leading down to a large protruding clit and a pair of neat but fluffy lips. As much as I love receiving blow jobs I equally love going down on a girl. I went to town on Evelyn, licking and playing with her clit whilst massaging her G spot with my middle finger. Before long her breathing got heavier and she tensed up and quite literally exploded. My first squirter!

As Evelyn recovered from her orgasm we headed to my bedroom and collapsed into bed. Before long Evelyn had my cock in her mouth again and was bringing me back to full strength. She then raised herself up and guided my cock into her now soaking wet pussy. I love it when a girl is on top as you get to watch her ride you up and down all the while playing with her tits and clit.

Evelyn continued riding me until she came again, just as hard as the first time. She leaned in and kissed me hard and said she was whacked and it was my turn to do some work. I rolled her over and lifted her legs up so the were resting on my shoulders. I started off taking long slow strokes giving Evelyn time to recover.

As the strokes got faster Evelyn pulled me into her and whispered “I want you to fuck me as hard as you can”. Who was I to deny this amazing woman what she wanted. I started pounding her harder and harder the sight of her boobs rocking all over the place as my cock slid in and out of her tight wet pussy was enough to push me to the edge. I told Evelyn I was getting close and she said she wanted me to come all over her body.

That was the final nail in the coffin, I pulled out and as I positioned myself over her, she grabbed my cock and started to wank me off. My first rope of cum shot through the air and hit her chin, the next couple covered her boobs. I was spent after having one of the biggest orgasms of my life.

I collapsed onto the bed trying to catch my breath, Evelyn rolled towards me and gave me a long passionate kiss. I would love to say that we stayed up all night fucking each others brains out but by this time it was after 3am and we were both shattered.

Evelyn got dressed and as I went to retrieve her thong from my jeans she waved it away and told me to keep it as a memory of our sailing trip. I walked Evelyn back to her hotel and that was the last I ever saw her. I still think about her now, especially when I have a bit of alone time in the shower.
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