I have dicked the boy I cherry popped, who I will call “cherryboi”, several times over the last few weeks. A few days after I popped his cherry, I got this sweet fucking e-mail literally thanking me for fucking him. He wrote, "You are the first guy that I have been brave enough to go all the way with. I have met 2 different guys in the past. One guy was in college and we messed around some and played with each other. We finished up by jerking off. The second guy was a guy I met about a year ago here in DC. He was so aggressive when we met that I got scared and bolted." So, cherryboi made it official. I was his first. Gotta say that I liked knowing that! Then in the hottest part of his e-mail, he wrote, "I was so scared when I got to your place that I almost bolted again. I wanted to be there, but I was freaked. I was able to get a hold on myself a little while we watched the game. The only thing that kept me there was that you took the lead and didn't give me any chance to change my mind. After we kissed I knew I had to have more! Thank you for making it so GREAT! The feeling of you cumming inside me was awesome. I fingered myself and tasted your load all night after I left. I will do almost anything if we can do it again sometime."
I am a total sucker for that kind of plea. After a few more e-mails and a chance meeting on H Street, not far from my place, we connected again. cherryboi is a delicious boi. He is every bite 6'1" tall. He says he is 25, but looks like a young college kid. He is athletic and lean and nearly totally smooth. He weighs between 175 and 185lbs. He has this sandy lifeguard-type blond hair that seems to be natural. It is a mixture of light and dark blond. His pubes and the other limited hair on his body are similar shades. He has a fresh looking boy next-door face with blue eyes, very long eyelashes and full lips. He is fucking tasty looking. I used him pretty hard, the first time we hooked up. Once I got the green light, I had my way with him including dumping a load in his tight ass. I'll be honest; there was a tinge of guilt on my part. So, I ignored the e-mails from him until I bumped into him on the sidewalk on H Street one evening after work. I was walking back toward my house and met him on the sidewalk. I would have passed him with a hello, but he wanted to chat. We chatted and he was low-key and friendly. He gave every indication that he was very pleased to see me. He asked me some random questions and as I was pulling away and saying my goodbye, he blurted out, "I'd like to come by again some time. I know I am not very experienced, but I am eager to learn." All I could do was smile and take his cell number.
About a week later, cherryboi was at my place bare-assed and between my legs with my hand firmly on the back of his head very assertively telling him how to suck my cock. I will admit that he was doing everything he could to try to do as I instructed. In the middle of his lesson, he gagged out that my cock was the first cock he had really ever sucked. And then for added effect, told me how thick I was. HOT!!! But like a good boi, he gave 110% to the effort and this time the head was better. The whole thing was a massive boost to my ego.
Then I took cherryboi upstairs, laid him out across my bed, crawled up and draped his legs over my shoulders, gently penetrated him and fucked him. He was still very tight, but this time I was a little gentler. He gasped and groaned as I worked my cock into him. I could feel the tightness of his hole clinging to my raw cock. Once I was inside him, I kept going gently building up a rhythm and listening to the change in his breathing and his moaning. As I started fucking him harder, he started to respond and I could feel his arms around me and his hands clinging to my ass. After about 15 minutes of me pounding him pretty deep and mixing it up with some full pullouts and short thrusts, I exploded into him and we immediately started to kiss passionately. I finally rolled over and lay down next to him admiring my good fortune and he moved in so that we could cuddle a little.
After a few minutes, I decided that I wanted nothing more than to fuck his well-jizzed hole again. I gave him a kiss and instructed him to go down and clean me up. I got up on my elbows, so that I could watch this hottie lick our juices of my cock. As I was sure would happen, he soon had a mouth full of hard cock. I asked him if he wanted a second load and without waiting for a response, I grabbed him and flipped him over so that I could get at him from behind.
This time his well-fucked hole was looser and my cock slipped right back in. He was still tight and clung to me, but he was filled with my load and the natural lube was incredible. The great thing to me about raw sex is the feeling of fucking a hole filled my your own cum. There is nothing like it. It is the ultimate form of topping. You totally possess the man your fuck this way. I owned cherryboi and he verified this by quickly shooting his load and using his moans of pleasure to coax my second load deep into him. I really dicked him this time.
We cuddled some more and chatted. It was very relaxed and I could tell that cherryboi was relaxed and comfortable in the aftermath of our sex.
He has been back several times since. Who wouldn't fuck this boi!
2 hours ago