I was married with a kid for 3 years at this point. Always been straight but sex life with wife was almost nonexistent at this point. Even when we have sex, I did not enjoy the sex and felt something was lacking. I resorted to watching porn and masterbating for release. I realized that I became more turned on watching gay porn. Initially was scared at those feelings but eventually gave in as a fantasy. After getting into gay porn, secretly downloaded Grndr in order to help with loneliness. Started a profile as someone in the closet and private, only looking for virtual fun. Had a lot of fun with some fun on webcam with mutual masterbation.
After a month on app, connected with a trucker who is in his late 40s (I was in my late 20s). He was tall, brawny, moustache, tattoos with dad bod. He described himself as bi and divorced. We hit it off immediately with mutual interest in sports and politics (he was politically very conservative). We eventually started talking about sex and I told him that I am in the closet with no experience with guy and current in curious stage. We had few fantasy roleplay and did some mutual masterbation on video. Slowly we bonded and he said he will be stopping at truck stop 2 hours from my place and staying the night for a delivery. He invited me to meet and grab lunch with him. Since we got along well I immediately said yes.
I drove the 2 hours, nervous the whole way since I never been on date with a guy. I left my wedding ring at home. Wore jeans, long black shirt and a hat with cowboy boots. Stopped at truck stop and went into a burger joint. Saw him sitting drinking a beer. After meeting him, felt very comfortable. We had some burgers, beers and played a little pool. After having a little too much to drink, I felt too drunk to drive back home. He invited me to his motel room nearby. I quickly accepted it.
Motel was 1 star, rundown smelling like cigarette smoke. We go into the room. He offered me a cigar and beer. We sat and chatted while watching football. Soon he said he had a gift for me. He gave me black lingirie (bra and panties) and heels. Told me to go to bathroom and wear it, he wanted to see how I look in it. I hesitated a bit, but I was buzzed enough I agreed.
I went into bathroom stripped down, wore the bra and panties. Wore the heels with pantyhose and was stumbling out of the bathroom. I found that he stripped himself down to his underwear sitting on bed smoking a cigarette and drinking beer. He laughed and said I look great. Told me to come closer in front of him. I stumbled in heels and stood in front of him embarrassed. He told me to turn around to show my ass. He slapped it and said I had a nice ass. For some reason that turned me on.
He told me kneel down in front of him. I did. He then told me to suck his cock. I was taken aback saying I have never done it before. He laughed and said there is always a first. He said dont be shy, try it. He also added he had a really tiring drive and needs a release and if I can help him. I went ahead and pulled his underwear down. He was rock hard with 8” cut cock dropping down. I was amazed at the size since I am uncut and small (4”). He told me to go ahead, he can tell from my eyes I want it. I slowly licked it. Didnt know what to expect but I enjoyed the musky smell and taste. Slowly started sucking him. He told me to look up while doing it and gave me a slap on the cheek. His aggressive behavior made me more horny and submissive. Started sucking him while looking at him. He slapped me again and told me to call him daddy. I said yes daddy while proceeding to suck him deep. After few minutes he pushed my head down and told me suck on his balls. I started putting his balls in my mouth and was very aroused with the taste and smell. Sucked both his balls while stroking his dick and looking at his eyes. Slowly after few minutes he kept pushing my head down while my tongue slid in his perineum. After a while he spread his legs and pushed his head down. I understood what he wanted and went ahead and licked his asshole. In the moment of orgasm, I started leaking a lot of precum while licking his ass. I never felt so alive.
Next, he pulled my panties down and told me to lay doggy on the bed. He took lube and slowly started fingering my ass, while I moaned. Soon enough I felt something big entering and realized it was his dick. I turned foward in fear and closed my eyes. Initially it was painful but slowly when my prostate got stimulated I went to whole body orgasms I have never felt before. After pounding me and slapping my ass, he turned me over. He then spread my legs in missionary and entered my ass again. At this point I was on cloud 9, moaning and screaming yes daddy. After a little while I felt a nice warm feeling. I realized he finished in me, and which point I relaxed and released a lot of cum. I then cuddled with him for an hour before he kicked me out saying he had to leave. I drove back home feeling satisfied and also confused about my sexuality. He ended up ghosting me but it was an experience that changed me forever.
This started a big change in my life that ended with wife catching me cheating, divorce and me eventually transitioning into a woman, which is a story for another time.
