When I was 18 and in high school, I had sex with this older guy who owns business and rental properties in my area. He was 59 and I came across his Craigslist ad some how. But he was looking for a 18 to 25 year old to be his "personal assistant" for the summer. He wanted a slim guy that could groomed well. I fit that description so even though I knew some sex was gonna be required I answered his ad. Since I was going to college that fall I figured I'd see what he wanted.

Three days later I met him at his house. Nice guy, well dressed, great house and very friendly. We sat on his back deck and he just got straight to it. He told me he's looking for a guy to help him check on his rentals this summer, mow the lawn at a few including his yard, call plumbers or roofers as needed and what not. Collect rent money and so on. He then asked my sexual preference and I told him I consider myself straight. He asked if I'm willing to have sex with a man and I said I am. He then told me along with the duties he already told me he also would be expecting his assistant to have oral sex and anal sex with him when he wants it and the pay fir the summer would compensate all of that.

When he asked me what I thought of it I told him the job sounds good but I'm a virgin. He told me not to worry as the guys the last two summers he had working for him were virgins too. So I told him I'll do it. He spoke my hard and said you'll enjoy this summer and make some extra cash before college. But first he required a drug test and std check so he gave me a paper for the test and I drove to the place where he sends all his workers for drug tests. But mine included an std check. He just got checked for stds and hiv a month before so he showed me his papers and that he is clean.

Next morning at 8am I was at his house and he explained the whole job to me. Including the sex part. That morning I gave my first ever blowjob and swallowed. His big 7" uncut dick with short pubic hair was hard when he pulled his briefs off. I was in an adrenaline rush giving him a blowjob. After I was done he said I wasn't too bad for a virgin.

Two days later when my tests came back all clear he told me after work that day to swing by his house. That day around 5 I was naked on his bed taking his dick up my ass. Though it was uncomfortable the first time I actually didn't mind it. He cummed in my ass after 20 minutes and then gave me a blowjob till I cummed my first blowjob was intense!

So for 4 months I got my ass fucked by him almost daily and gave him quite a few morning blowjobs. All while my mom wondered how I found such a decent summer job. I got paid for my hours working plus extra cash each time he fucked me. He'd hand me cash after I got dressed saying he always likes to give some cash at the end of the day especially after he cums in the guys ass. I'd be laying in bed at night in just underwear (briefs at the time) with his cum seeping out.

Last day I worked for him he paid me for the whole day but I blew him in the morning, took his cock for lunch then that evening he fucked me one last time. After that he told me to get an std check tomorrow to be safe and come back in a few days for the results. Went bs I a few days later, I was still clean and he gave me my last pay check. Won't say how much but it was a nice big one and he gifted me a MacBook saying I'd definitely need it for college. He also gifted me a few clothing items including a suit and some Calvin Klein briefs saying I'll be bee that stuff for job interviews at some point. He shook my hand and I left.

Started cold two weeks later and met my now wife,