Where it happened: at home
Langauge: english
Sex: Male
Rating: 5
Category: Straight
I suppose it all started when I was five. I know this because my mother kept a diary that I found and regularly read when I was ten. Mother started me on weekly enemas when I was five (according to her diary entry). She wrote that I seemed unhappy about getting enemas at first but as time went on I seemed to accept the process and even came to enjoy them. I would even offer suggestions as to the temperature of the water, I liked it very warm. Sometimes, she wrote, I would mention that I had not “been poo” for a day or two. This would always result in an extra large enema which I definitely remember. I tell this because I think this is when I discovered how exciting it was to me to have my anus penetrated.
The enemas stopped when I was eleven, not because I wanted to stop, but because I was getting rather strong erections that mother must have noticed.
When I was almost twelve a local teen boy talked me into sucking his penis. He was probably about fifteen at the time and I was afraid he would tell our friends about me sucking him, but he kept after me until I did it. I was surprised at how I liked both the hard/soft texture and the taste. I was beginning to get into the action when we heard his mother calling. He didn’t cum and that was a good thing because I knew nothing about ejaculation. We never repeated our sex play. He was too old for me anyhow
My mother divorced and remarried when I was fourteen and we moved away. So that brings me to the point in my life when it was time for me to learn about sex. My step-brother Phil, sixteen years old, entered my life and things got really interesting. He was quite handsome and made me feel like a true friend. We roomed together and went to the same school.
Phil and I had been given the job of weeding the garden in our secluded backyard. Our parents were at work and we had the whole day to ourselves. It was a hot day so we decided to work in the nude. Phil had been trying to educate me sexually for several months. One night, before our parents were married, he slept over at our house. My mother and his dad spent the night at his house which was just up the street.
After we went to bed, naked, of course, we started fondling each other. He rolled over and kissed me on the lips. I was surprised and pleased, especially when he put his tongue into my mouth. We kissed for a while and then he asked me if I had ever been fucked before. I didn’t understand. Remember, this was before the internet. I did’t want to seem so dumb so I said I hadn’t yet, but I might like to try it sometime. Then I asked if he had. He told me a boy we both knew had fucked him once. So we talked about how it felt and he asked if he could fuck me. I said yes and we found some vasoline and he put some on his finger and slowly pushed it into me. This brought back memories of all the enemas I had had and how I liked haveing the enema nozzle inserted into me. He played with me for a while and I said he could put his penis in if he wanted too. He was about six inches and cut. His penis had a bend to the side that I thought looked odd. He put vasoline on his penis, rolled me over onto my belly, asked me to spread my cheeks and then he began to push himself into me. It was so tight and he felt so big, but I didn’t want him to stop. When he had the head just past my anus, I felt like I was going to split open and cried out for him to take it out. He did immediately and let me rest for a couple of minutes. He told me it hurt him the first time too, but that it would feel better in a little bit. My anus finally quit throbbing and I told him to try again a little slower. So he slowly thrust into me and he was right, it did feel better. In fact I really liked the full feeling he gave me. He told me I was really tight and hot on his cock and I told him to work it back and forth a littled. I still remember how good that felt. I got a really hard boner as he rocked back and forth. Soon he began to go deeper and faster and I started sweating as he moved in and out faster and faster. Suddenly he moaned as his head dropped onto my shoulder and I felt him jerk several times. At last he collasped onto my back, his penis still in me. At this time, I had never cum so I really did not appreciate how excited he was. He laid on my back breathing heavily and I felt his penis becoming softer. He finally slipped out of me and I felt wet and slippery in my crack. He rolled off of me and kissed me once more. Then he said something I have never forgotten, he said “I love you”.
Tears of joy rolled down my cheeks. No one had ever said that to me before.
I would have been content to just lay in his arms the rest of the night, but he wanted me to fuck him! I was really nervous and excited too and I told him I didn’t know exactly what to do. So he had me put vasoline on my finger and put it in him just as he had done to me. I was amazed at how tight and hot it felt on my finger. (Boy, did I have a surprise coming!) Soon he put vasoline on my penis, which was only about five inches, lay on his back with his legs pulled way up and had me slide my slippery penis into his ass. Oh wow, what a feeling! I had never experienced anything like this before and I was loving it. He locked his legs around me and pulled me down onto his belly and chest. As I moved in and out of him we kissed and kissed and kissed. Then the phone rang and I jumped up, popping out of him and ran for the stupid phone. It was my mom just asking how things were going. I told her we had finished our homework and were about to go to bed. She said we should shower first and she would be home early and fix breakfast.
By now my erection was gone and I still felt sticky and wet in my crack. The excitement was gone and we took showers together. Phil washed my butt and told me his cum was running out of my anus. (So thats what the wetness was!)
We continued our sex games and he fucked me fairly often. Whenever our parents were gone. I fucked him sometimes, but never managed to cum, still too young I guess. Of course, we did other stuff, especially sucking which I really liked doing. Phil always told me when he was about to cum so that I could take his cock out of my mouth, but I always sucked him dry.
Now, back to my first cum. We were weeding the garden in our secluded back yard. Nude. Parents gone. We finished the job and went inside to shower. After the shower, I asked Phil if he felt clean inside too. He said “I guess so, what do you mean?”
“Well” I said, “I feel like I would like to be cleaned out with and enema. Would you like one too?”
“Gee, Bobby, do you know how to do that?”
“Sure, Phil, I’ve had lots of them. It feels good. Not as good as when you fuck me, but I like it anyhow”.
Phil said he would try it if I would too. So I got out the old trusty enema bag and nozzle, filled the bag and told Phil to bend over the side of the tub. I put a little vasoline on the nozzle and slid it up him. I had put some warm water in the bag and slowly released it. He said,”Gosh, that feels sooo good!” I emptied the bag into his ass, removed the nozzle and had him expell the water into the toilet. Then it was my turn. Phil was a fast learner and gave me a great enema.
Now we were both cleaned out, excited and ready to fuck!
Phil fucked me first and when he had finished I stood up and let his cum run out of my ass. Now I got ready to fuck him. This time I felt different. My dick had grown a little and I had a little hair around it. But the funniest thing was the slippery stuff oozeing out of my cock. I had never had that before. I told Phil to lay on his belly, spread his legs and cheeks and then I stuck my dick all the way in on the first thrust. He grunted and said I must be be in a hurry. I had never felt so hot like this before. His anus was gripping my cock tighter than it ever had before. I thrust into him as hard as I could, not because I wanted to hurt him, which I didn’t, but because I was so excited. I began to go faster and faster and then I started to feel like I might pee. I didn’t care, I just had to keep going even if I did pee. Suddenly, I began to feel my legs tighten up and I pushed into Phil as hard and deep as I could and the most wonderful feeling overcame me as I felt something hot and thick spurting out of my dick. After severeal spurts I collapsed onto Phil’s back and lay panting and exhausted. My heart was pounding so hard I thought it would burst out of my chest. At last my dick slipped out of Phil’s ass and I rolled off of him and just started giggling. I had never felt so good in my life! He said he thought I was going to shove my balls up him too.
Well, that’s it, my first time.
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