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[F23, M50’s] Fucking a man over twice my age
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This story happened almost exactly ten years ago when I (F23 at the time) was travelling through Asia. I was in Thailand for two weeks and befriended an American girl my age called Katie. We were staying in the same hotel and kept bumping in to each other. We ended up hanging out together and we got on really well. She was exceptionally pretty, a brunette with a killer body. We spent most of our time in swimsuits and bikinis and she turned heads everywhere we went.

Katie mentioned that her dad was going to be visiting for a week. He timed his holiday to meet up with her in Thailand. She had been travelling for a few months and was really excited to see him. She explained that he was widowed after her mom passed the previous year, so it was probably hard for him with her being away and her brother in college.

He arrived and Katie was spending a lot of her time with him, and she talked about him and the things they did together quite a bit. We were out a few evenings later and he showed up to have a drink with us. He was staying at another hotel.

When I met him I was instantly struck by how handsome he was. Im not sure what I was expecting but he was probably 30 years older than me and had grey hair but he was in great shape. He reminded me of those older guys you see in a Gillette ad on TV. He spoke with a thick American accent, he was fun and insisted on buying us drinks all night. We had a nice evening with lots of laughs.

A few evenings later I was walking on the beach and I bumped into him walking against me. Katie was off on a night out with other friends so he was by himself. He recognised me and stopped to chat. There was a beach bar right nearby so he asked if he could buy me a drink. I got a feeling that it may not be appropriate but agreed as I didn’t want to be rude.

We sat outside and chatted for a while and before I knew it we were three drinks in. He was great company. He asked all about my life, the career I wanted etc. He happened to be a lawyer which is what I studied in college. I felt really comfortable and was surprised to find myself attracted to him.

‘Would you mind if I kissed you’ he asked out of the blue. I was stunned but blurted out ‘sure’. He put his lips to mine and we kissed for a moment. This was totally wrong I thought to myself. He apologised and said that he just found me irresistible. He got up and said that he would leave, apologising again. ‘I liked it’ I said, with butterflies in my stomach at this stage. I was used to being kissed by men but he was so much older.

He then asked if I wanted to go back with him, his hotel wasn’t far and he assured me it would just be another drink if that’s all I wanted to do. I agreed and we made our way back to his hotel. His hotel was much nicer than the place Katie and I were staying at, pretty much five star with marble floors and huge high ceilings.

We brought a drink up and talked another while. His room was huge with a seafront view and massive queen size bed. We were sitting out on the balcony and after a while he put his hand gently on my back. I instinctively turned to him and we kissed again. We got on the bed and kissed and fondled each other, fully clothed for a minute or two.

Gradually our clothes started coming off until I was down to my bra and panties and he just had his shorts on. He unhooked my bra and started kissing my breasts and nipples. The thrill of being with this man over twice my age is hard to explain but it felt so good, probably because I knew I shouldn’t be doing it.

Within a minute or two my panties were off and he was eating me, licking my clit on this huge bed with his hands firmly grasping my thighs. His technique was amazing and I was loving it. He gradually put his fingers in me and started rubbing, driving me wild. I cried out as he made me cum, leaving my pussy tingling and my legs trembling with pleasure.

He took off his boxer shorts and I got my first glimpse of his cock. He had a nice thick shaft, it wasn’t huge but it was a good size. I went down on him, bobbing my head up and down with my lips and tongue tight around his cock as he held my head gently. I put my finger in his ass and started massaging him and from the sounds he was making I could tell he liked it. Within five minutes I could feel his whole body start to tense up. I upped the tempo to drive him wild. He groaned loudly and yelled ‘fuck’ as he came in my mouth. I kept my mouth on him until he stopped pulsing and squirting before running to the bathroom to spit in the sink. ‘That was fucking amazing’ he said as he watched me walking back to the bed, completely naked.

We got under the sheets and continued to kiss and fondle each other. He was hard again soon and I whispered ‘fuck me’ in his ear as I edged him. I always used condoms at that point, but I was on birth control and figured this was a family man in his fifties so he was almost certainly not going to have an STI. I thought ‘fuck it’ and just let him in me raw.

He started fucking me missionary as I put my arms around him and gently controlled his strokes while kissing his neck and face. I wondered if I was his first since his wife passed as he continued to plunge his cock into me. It took him a while to cum but he let out the most intense moan I have ever heard when he did. He stayed inside me for about another minute, breathing heavily as I had my arms around him. ‘You have no idea how good that was’ he said to me as he eventually pulled out.

I hadn’t meant to stay the night but I was tired and probably still a little hungover from the previous night, so I fell asleep.

When I woke up he was already awake and lying beside me. ‘Good morning’ he said as I came around with the previous night flashing before me. Oh Jesus did this really happen I thought. He moved over and kissed me on the forehead saying something like ‘I hope you slept well’. We were both still naked from the night before and I could see he was already semi hard.

We started kissing and before I knew it he was inside me again, thrusting hard, much harder than the previous night. I liked it and encouraged him, grabbing his ass tight and pulling in every stroke. After a few minutes I gently pushed on his chest and signalled him to get off before turning around and getting on all fours for him. I loved getting pounded doggy style and he didn’t disappoint. He rammed me hard as he pushed his cock into me again and again, switching between holding my hips and slapping my ass. Eventually he grabbed my hips tight and drove his cock as deep as he could while groaning loudly. I could feel him pulsing hard as he delivered a load of thick cum inside me.

I collapsed down on the bed with him still inside me, he stayed like that for a while, propping himself up on his elbows so that his weight wasn’t on me, but his cock still firmly inside. It’s like he didn’t want it to end. He started kissing the back of my neck and behind my ears and whispered that he would never ever forget this.

He pulled out and we cuddled in bed for a while before I told him I had to go. It was early but I had plans to go snorkelling with friends that day and I was afraid Katie could knock on the door at any minute. He kissed me and thanked me for such a special night before I gathered my clothes and left. To be honest it wasn’t the wildest sex I ever had, but I guess fucking a hot, busty girl his daughters age must have been an absolute thrill for him.

I only saw Katie a few times after that as she spent a lot of time with him. She left to continue travelling at the end of that week and presumably she never found out that I fucked her dad. I secretly wondered what she would have thought if she knew. Katie was very open about sex and had slept with at least three guys I knew of in the short time we were hanging out. It’s not like we were childhood friends or grew up together either, so I can’t say I felt any guilt or shame. She had also spoken to me about how lonely her dad must be. Maybe she would have been happy for him to get his rocks off with me I thought to myself, as if trying to excuse or justify my behaviour.

I have slept with older men since but to this day Katie’s dad was the biggest age gap I’ve had. He was so gentle and kind and really hot for his age, and our night together seemed to make him so happy. I’m glad I did it if I’m honest.

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2 months ago