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First Time

"First anal"

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When I was 18 I went to a Tech College and had a free afternoon once a week. I’d go home and study for a bit and then often have a browse through my collection of porn mags and have an uninterrupted wank whilst no one else was home. My parents had some kind of life insurance and the premium was paid to a door to door collector who would call once a week. My parents got on well with the guy and invariably he would stop for a cup of tea. When mum started working, the insurance guy started coming to collect the premium on my free afternoon. I’d make Simon a cup of tea and we’d have a chat. He was always a bit touchy/feely. Sometimes he’d rest his hand on my thigh or gently stroke my leg. This started giving me hard ons! One time I caught Simon looking at the bulge in my jeans and I just blurted out that I had a stiff one! Simon just grabbed me! It was so sudden that I fell off the stool onto the kitchen floor! Simons hands stroked and rubbed me as I lay there! I wasn’t sure if I wanted things to go further and removed his hand from my crotch with some difficulty. His hands then started caressing my bum cheeks and one finger started rubbing on my hole! Again I wasn’t sure about this and took his hands off me, however his hands returned to my cock! I was confused about my feelings and sexuality. I asked Simon to leave and he did after apologising for rushing things. I thought about what had happened and rationalised that I still liked girls, but there was nothing to stop me having fun with a guy - I hadn’t heard of bisexuality in those far off days! The next time Simon called I had a raging hard on and as soon as I had locked the door, I unzipped and released my stiff cock! Simon gasped and said “Ooh you’ve got a nice one!” He drew me to him and gently started to wank me off. When I was about to cum, my cock made tiny spluttering noises before releasing a jet of spunk across the kitchen floor! It was the best orgasm I’d had to date and left me weak at the knees! I sat down whilst Simon made some tea and gave the floor a thorough wipe. That time and the next few times Simon didn’t ask for any reciprocation, he was just happy to wank me off and I wasn’t complaining! One time I was bent over looking through the serving hatch into the dining room at the tv because I was interested in the news item. Simon sneaked up behind me, unzipped and started thrusting his cock at me though my trousers! The feeling was amazing! I was thinking about just dropping my trousers and letting him have his wicked way with me when the doorbell rang! It was my little brother who had been sent home from school a bit early because of staffing issues! Anyway, that put paid to the fun that afternoon! The next time (and in fact the last time with Simon) we were not interrupted! We both had our cocks out and were slowly wanking each other and rubbing our cocks together.Suddenly Simon undid my jeans and pulled them and my pants down to my knees. His right hand snaked around my waist and then stroked my bum cheeks. His middle finger found my hole and was rubbing it gently. His fingertip on my virgin bum hole felt incredible, I’d never really thought of my bum in a sexual way before! Simon turned me around and applied lots of saliva to my bum and then eased his cock up me! It didn’t hurt and felt decidedly naughty and enjoyably wicked! As he fucked me, Simon reached around and wanked me off. I shot a thick rope of cum as he pumped my arse full of creamy spunk (this was in the pre AIDS/HIV days) I still remember the feeling of spunk oozing out of my well fucked arse! Sadly I went off to university and when I returned Simon had left his job and I didn’t have his phone number.
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