My first 'older man' experience.

I thought I would share details of my first experience with an older man. It was 5 years ago and I guess it was life changing, as ever since, older men have always been on my radar.

I had known Simon all my life and still do. He and his wife of about 25 years or so (Jayne) are two of my mum’s closest friends. It was obvious that he began to look at me differently though after I headed for college, and things reached their peak on a weekend back at mum’s when she had organised one of those murder mystery parties. At the time I was 19 and Simon was 55.

Present were me and my then boyfriend Steve, or cuddly Steve as he was known due to his size. Steve is a great, great guy but wasn’t the most sexually active of boyfriends and spent the latter part of our relationship studying or playing computer games!

Simon and Jayne were also there along with my mum and stepdad and another couple.

My character in the murder mystery had to role play with Simon’s quite a lot. I was a saucy French ex singer and he played a detective who suspected me of the crime. As the drinks flowed there was lots of flirting between most characters, but at the end of the night when the game was over and I was putting the empty bottles in the garage I felt a grab and rub on my arse. I assumed it was Steve ready for some late night nookie but to my astonishment, when I turned around I saw it was Simon.

I was horrified and I slapped him in the face and told him as quietly as I could to fuck off. He immediately exited and I stayed in the garage momentarily to compose myself and think things through.

I went to bed where a d***ken Steve was already passed out but given what had gone on I was sober as a judge and couldn’t sl**p. Simon! When I was younger I had called him Uncle Simon due to the fact that the families were so close! Jesus! I thought more and more in bed and felt I’d been harsh on him. He was a lovely man, and kind of cute too with his head of white hair and his beard. He was another big cuddly bear who you could just cuddle all day.

In bed with Steve completely out of it, I began masturbating and got myself off thinking about Simon and potentially making love to him. It felt amazing and I had to try really hard not to shriek and wake the house up.

The next morning, I had to be cunning and act fast. Mum and Jayne had planned a shopping trip, while my stepdad, Steve and Simon were due to have a boys day and go to the football. I had arranged to see some friends back home before me and Steve headed back for college the next day.

However, once I saw Simon head for the bathroom and that the coast was clear, I sneaked in behind him and told him to make an excuse to get out of the lads day and stay in the house as we needed to talk. He told the others he didn’t feel well and got made fun of for having a hangover. I didn’t mind. I made it look like I was off to see friends before returning home 20 minutes later when everyone else was out the house. Me and Simon would be alone for at least 6 hours.

Upon entering the house again through the side door, Simon was making tea in the kitchen. He immediately apologised for the previous nights actions but I apologised for my over-reaction, putting it down to shock. I asked him where it had all come from and to be honest with me. He said I was beautiful and he was crazy about me. I leaned in and kissed him and from then we were all over each other. He was so gentle and tender and soft.

At first I had to tell him to put his hands where he wanted and that I was all his and after a few minutes he got the message and was rubbing and squeezing and feeling me all over.

Soon we were upstairs, he in just his underpants and me in my knickers and bra. He took the bra off and gave my breasts plenty of attention before we climbed on the bed. I removed his pants and went to town on his impressive cock, sucking and kissing and licking to my heart’s content. After plenty of cock envy, he was down on me, and it was clear that the older man, after year’s of experience, knew how to lick pussy.

The love-making was exceptional. He was right inside at all times and we were kissing throughout and worshipping each other. He came all over my chest and I was sure to get some on my fingers and have a taste. After mopping up, we just lay in each others arms for a while kissing and talking. It was amazing.

We showered together and then decided to take the dog for a walk, but within minutes of the walk we were all over each other again in the woods at the back of my mum’s house. We couldn’t go any further, we had to get back to the house and get naked again. The poor dog didn’t know if it was coming or going.

Back in bed, and fucking much harder and louder this time, Simon shot his load all over my arse cheeks. We were both in heaven.

So began an affair that I guess still continues today. We don’t see each other very often, although that particular year from 19 to 20 we did hook up a couple of times with Simon often telling Jayne he had to go away on business before meeting me where I was at uni. We would stay in a hotel for the night.

We’ve not been intimate together for over 18 months now, but if the right circumstances came along I’m sure it would happen again.
90% (32/3)
Posted by chess4000
3 years ago    Views: 1,616
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3 years ago
Lovely story! xxx
3 years ago
older,more expeirienced
more should try :)
3 years ago
3 years ago
Very nice story, well written and I like your style. I'm still in a relationship that started 12 years ago when she was 18 and I 50. It's still amazing. Thank you for posting.
3 years ago
Great time and story