My Bisexual Encounters Pt. 01

My name is Drew, and this is my story of my bi life.

I am currently 48 years old white bi male in decent shape, and I finally decided to sit down and write about my encounters over the years as I have had the pleasure of reading others over the years. I truly consider myself Bi and not gay, my stories below focus on my Bi encounters only.

My 1st encounter with a guy happened in my senior year of high school and I was 18, I was delivering newspapers, and this was back in the 90's when you still had to go and collect payment from the houses. Long story short I started to have an encounter with one of my female customers. She was older in her 30's not fat but bigger, we had nice encounters or oral and sex over a month or so until one night I was there, and her boyfriend was there for the 1st time, never met him as he worked nights. I was very nervous and tried to leave but she persuaded me to stay and stated he knew of the encounters and wanted to watch.

Being very horny I stayed and fucked her while he watched and jerked off. After fucking her and came I was laying on the bed and she stared to rub me getting me hard again and blew me. He approached me and before I can do anything he took my cock in his mouth from her and gave me a blow job until I finished in his mouth with him swallowing it all. At this point I was very nervous as this was my 1st encounter with anything guy related so I got up and dressed quickly and wanted to leave. As I went to leave, they both walked with me and stopped me at the door, he spoke and said was that your 1st time and I just shook my head yes.

He then grabbed my cock thru my pants and said why don't I come back on Saturday afternoon, and he can teach me more, I just said OK and left. The rest of the week I thought about what happened and should I take him up on his offer. After much back and forth and nothing to do on that Sat afternoon I went over to the house. I rang the bell, and he opened the door with a smile and let me in, he said she was out, but this was about him teaching me today, he then guided me upstairs. Once in the room he asked me to strip and get naked and he did the same, he then pushed me down to my knees in front of him and said let's start with the basics as he grabbed my head and told me to blow him.

I did what I thought I should do as he guided me and taught me the right way. After a couple minutes he pulled out and had me get on the bed where we hoped into a 69. I was enjoying this and after a couple minutes we both blew our loads with him swallowing everything and me taking some of it while the other dripped out of my mouth. We got up cleaned up and he guided me back to bed where he rubbed my cock and brought ne back to life. As we laid there both getting hard again, he asked did I like this and I said I did, while he was rubbing me, he was also pushing his fingers down to my ass and rubbing my hole making me squirm. He was making me feel amazing, and he said the next lesson is to let him fuck me, and asked did I want that, I just said not sure, but he said trust me.

He then rolled me over on my stomach and started to play with my ass using his fingers to rub and slowly insert in me, he had me very worked up and I was enjoying what he was doing. He then grabbed lube and got me loose and then I heard him opening a condom followed by him trying to push his cock in me. Won't lie it hurt like hell and I was moaning out in pain as my face was buried in his bed, I believe he got the head in when I tried to pull away and he said to relax and held up for a little to let me get used to it.

Finally, he was ready to move on and he pushed his cock in me very hard that made me pull away and say I was done. I flipped over on my back and said no problem we can try that again later but then took my cock in his mouth, then he let it slip out and got on me lowering his ass onto my uncovered cock, he must have had lube already on his ass because I slipped right in as he rode me for about a minute before releasing my load in him. After I got up to clean up and said I had to leave, he walked me out and said I wasn't bad for my 1st time, he then grabbed my cock and said we will make you fag over time, and to come back next Saturday. I left and regretted what happened never returned to that house, I delivered their paper in the morning but never collected their money and by summer I quit that job and never saw them.

After that 1st time and a couple weeks the regrets became jerk off fantasies and realizing I enjoyed what bi sex could be but not with him. I started to go to adult bookstores to buy toys to play in my ass but did not know how to act out for real with someone else wanting to be discreet.