My taboo was last year. One of my sons friends (he was over 18, yet still in high school) was wanting to work with my son and I at my business. So he started tagging along. There was a period of time, my son who is a year and half younger than him, wasn't allowed at his house because his mother thought he and my son were more than friends. My son is straight and she never had reason to think he wasn't. However moms know their sons... so I figured she knew her son was into guys. He is an athletic built, muscular, jock, football player, and country boy, a handsome 5 foot 11, 160 lbs, 29 inch waist. I got to spend a little more time with him around my house he started setting off my gaydar.. The way he would look at me and other friends of theirs at my house really set it off. One day him and I were alone and he said some old guy had hit on him and he said he was straight. I looked him in the eye, i smiled, we were almost face to face. I leaned in and whispered in his ear, we both know thats not true, but I wouldn't have known unless I also had the same interests. And I smiled and he shook his head like he understood what i had told him. I gave him a hug and told him his secret was safe with me and it changed nothing about him and my sons friendship.
A couple months down the road, I had to travel for work and my son was unavailable to accompany me. He asked could he come on the overnight trip 4 hours away. I didn't see an issue and he tagged a long to help me. He's almost 19 at the time. Well on the drive up, I told him we would be sharing a hotel room but not a bed and he said "oh okay, I don't care." We did some of the work and got ready for the next day, went to eat supper and then to the room. When we got in bed he got down to his underwear which we had both been in each other's presence in our underwear before because of times he spent the night with my son. We were in our respective beds and he started opening up about what he wanted and then asked if it was okay if he slept naked. I said I don't care. He said I know you like to sleep naked too. I said I did but he was in the room. He said he didn't care. I didn't feel like removing my underwear. So we continued to talk and he stated he never had been on bottom but really wanted it. He said "how about in the morning you just come get in my bed, I'll be naked and you can do me" I said "you want me to put it in you?" He confirmed with a yes. I said "I'm on the thick side of things and he should probably see it before he agreed to take it" so he asked me to show him. So of course I'm very hard. Oozing precum. This virgin, cute, small built, country boy, with a 29" waist and 8" tool wants me to take his v card. It was dark and I told him he should come check it out to be sure. He came and got in my bed. He started checking it out with his hand and I started squeezing his and stroking it. I said since you're here why don't we just go ahead and do it now. He shook his head yes. I kissed his slim body made my way to his dick to give him oral pleasure. In the process I started to finger his hole to get him loose enough for me. I generally always keep lube/condoms in my overnight bag and I grabbed the lube from there and started lubing up my shaft. I continued oral and down to his hole with my tongue. When I felt he was ready I got a pillow and put under his butt. Put a towel under him on top of it, and I made my way into him. As I got into him and he relaxed to take me. The look of pleasure on his face was amazing. I pulled out and added more lube then proceeded to pump his virgin hole faster and faster. He starts moaning, flexing, and he finally grabs his 8 inch cock, and gives it 3 or so strokes and shoots himself in the face with 4 or 5 warm loads. The rest on his chest and tummy. This sent me over the edge of course and I filled his tight little hole with a huge load. I licked up the cum on his face and he was smiling so big. We got up and headed to the bathroom to clean up. I'd never seen his bare ass until I followed him from my bed to the bathroom. It was amazing and I was chubbing back up. He was the sink still hard himself. I got behind him wrapped my arms around him and eased back in. I fucked him again eventually leaning him over in front of me so I could see my cock pumping just below his cheeks. I came in him again. I pulled out and we got into the shower to clean ourselves up. Afterwards he slept naked with me. It was the hottest sexual experience I've had in many years. I've only given him oral one time since but he had my 5" dong in him while I sucked him. He had spent the night and my son had left the house. It was just me and him there. He had asked me about ordering him a toy. I showed him mine and he wanted to try it out. So i stuck it to the shower wall and put him against the wall and sucked him. I never even wanted him until he mentioned it. He turns 20 this month and is engaged to be married in the summer. My son doesn't know and we agreed to keep it from him. My son does know I like both men and women.
