First Time Fucked.

This is the true story of the first time I was ever fucked by a guy:

I started having gay sex when I was 18. My first experience was with a guy I met through a female friend with benefits while I was still in high school. He was not the first guy who fucked me in the ass. He did teach me how to fuck a guy in the ass with my cock though. He taught me the importance of holding back until just the right moment to cum. He also gave great blow jobs and taught me how to give them and how to swallow cum without gagging. I had sex with him and other men as a top for about 2 years in the early 1990's.

Fast forward to about 1992. I was attending a small business college in Des Moines, Iowa where I lived at the time. I rode bike to and from school. One day on the way home I was going down a hill on the trail I was riding on. As I applied the brake to slow my descent the brake malfunctioned and the pad wedged under the rim, stopping the front of the bike instantly, throwing me over the handle bars superman style.

Thankfully I hit the grass and dirt, but chest first as I lifted my chin as I made impact with the ground as to protect my face. As I hit and bounced my heavy back back, which had slid back while I was in the air flew forward and smacked me in the back of the head, pushing my helmet over my forehead and eyes.

This area of the trail is an access for other trail users with parking. Another guy who had just finished a run saw this happen to me and came running over to see if I was alright. I was trying to get up but could not see and my chest hurt as it was very hard to breath. He told me to lay still in case I was seriously injured. He didn't push and hold me down, but put his hand on my back to calm me. I calmed down and didn't move, except to put my arms under me to hold up my upper body while I lay there on my belly. It was then I realized why I could not see. I rolled slightly to my side and to move my hand and arm up so I could take off my helmet. He saw this and helped. I again tried to get up some more but he told me to hold on. He started asking me questions, who I was, did I know what day it was, etc. He asked if anything hurt to move or if I lost any feeling anywhere. I answered his questions and told him I can feel everything. He helped me sit up and take the back pack off. At this point I had caught my breath and it did not hurt as bad to catch my breath. So I stood up and looked back at my bike. Which was about 10 feet from where were standing. I checked it out and it was not in ride-able condition. Keep in mind this was before cell phones. Even so no one was home to come help transport me home.

He asked where I lived and I told him another 5 miles on the south side. He lived just a mile or so away and told me I can come with him so I can get cleaned up and call home when someone was going to be there. I was a mess after hitting the ground. He had a truck, so we loaded my bike in it and went to his place.

When he said get cleaned up I did not think he meant I could use his shower. He did and I changed into the regular clothes I wear at school as I had bike clothes on at the time.

While I was in the bathroom I noticed some gay porn magazines in an old antique magazine rack. I didn't think anything of it, since I like gay sex too. These showed a lot of older men fucking younger guys though. While it turned me a bit I was in no shape to jerk off or have sex.

After my shower I called home, but no one was there but knew someone would be home soon. He invited me to wait and talk with him. He told me what he does for a living and how old he is. He was 60 at the time, I was only 21.

I decided to take a chance and brought up the gay magazines in the bathroom. He was not embarrassed or anything and asked if I like gay sex. I said I do. He asked what I do. I told him I like to suck, get sucked and fuck. He asked if I fuck bare back or with a condom. I stated I prefer bare back. It feels better for me and the other guy when I cum, but will wear a condom if the other guy asks me to. He then asked if I have ever been fucked. I stated no. He asked if I ever thought about letting a guy fuck fuck, I stated I had not given it much thought. At that point he advised I call home again. I did and someone answered. I told them what happened and that the guy who helped would bring me home.

On the way to my house I asked him what he likes to do with guys. He told me suck, get sucked, get fucked and fuck. I stated I wish I was in the mood for sex. He advised better to wait until I feel better but invited me to call when I am ready.

He dropped me at home. The next day I figured out he was right about waiting. I was very sore and bruised. It took a good week to feel better.

Then one day before I left school I called him and asked if I can come over for sex. He said yes and could not wait. I arrived at his house. When he answered the door he was naked. He was beautiful. Nice, thick, uncut cock, it looked about 5 inches when soft. I had never been with an uncut man before and could not wait. I stripped naked and got down on my knees. But he wanted me to shower first. So I did. When I was done he was in his bed waiting for me.

I got into bed with him and we started stroking each other. He then sucked my tits and squeezed my ass, then moved to my cock. I knew I would cum if he was half as good at giving a blow job as he was at sucking my tits and stroking my cock. I warned him I don't want to cum yet. He stated he wants to swallow it. He took me deep in his mouth. After a few pumps into his throat I emptied my balls and he swallowed every drop.

After we lay there but i was disappointed it was over so early. He got up and so did I to get dressed. He said no, we were not done and stood there with his hard 8 inch cock before me. I went down on him taking as much as I could in my mouth. I discovered very quickly I loved the feeling of the foreskin of an uncut cock sliding up and down in my mouth as I performed oral sex on him. this turned me on so much I started getting hard again. He started moaning with pleasure. I knew he was getting close so I backed off. I wanted to control when he same. After a little while of bringing him to the brink and then backing off I finally let him cum in my mouth. He tasted great. His cum was thick and creamy with just a hint of saltiness to it.

After we recovered from that he wanted me to fuck him, bare back. I got behind him, entered his ass and started fucking him. While I was fucking him I noticed he moves his ass like a woman does her pussy. He was squeezing his ass cheeks together, move back and forth, etc. This felt incredible as i have never had a guy do this when I fucked one. It did not take long for me to cum deep in his ass.

After we both took a shower and I went home.

After that we saw each other at least once a week. We would pretty do the same things sexually but did change it up on occasion. We even had a few 3-somes with other guys and even a few women.

Then one day when I arrived for one of our hot sex sessions he brought up the magazines I first saw the first time I met him. He asked if I remember what was in them. I said sure, older men fucking younger guys and asked why. He then asked, since I have been with him if I thought about being fucked. I did admit I had thought about it. We talked about it for a bit. It was then I decided to let him fuck me and deflower my virgin ass but was worried it would hurt too much. He said not to worry he has a technique that is painless. Here is what happened:

He had me lay on my back, legs together. He lubed the entrance to my butt hole. He told me he will talk me through the whole thing. He also said to control my breathing while he penetrates me. He said, when he tells me to, take a deep breath and let it out very slowly as he enters me and when I run out of breath he will stop s I can take another and breath out slowly as he penetrates me until he is all the way in.

He straddled me and put his huge cock head right against my butt hole and pushed in a little to open my cheeks and hole just a little to make sure he would not slip out of position. I could feel the heat from his massive prick, it felt like it was blowing into my tight virgin hole. He told me to take a deep breath and to start letting it out. I did so. As I let it out he started penetrating me. First the tip of the head of his cock opened my hole and entered me. Then I could feel his entire hear in me. It felt intense, very hot, as in the physical feeling of heat, there was a lot of pressure, but no pain at all. He got about a quarter of the way in and i ran out of breath. I quickly took another deep breath and he continued to penetrate me. I could feel the thick veins on his cock against the inside wall of my rectum. i also felt ever ridge and bump on his cock. Soon he was all the way inside me. He stopped and did not move. He asked how I feel I told him there is no pain, just a lot of heat and pressure. He said when he fucks me he will only pull out as far as just before the head comes out and push back in and will continue this until he cums. So he did so. He fucked me, and fucked my virgin hole good. I could feel his foreskin move back and forth or in and out as he fucked me. That first time he was pretty steady. But I did indicate I was enjoying it by pushing back onto him as he fucked me. He increased his thrusts into me until he finally exploded his cum in me. It was the most intense and hottest thing I have ever felt to this day.

After we were done I fucked him and we lay there in each others arms until I had to go home.

After that we had sex at least twice a week.

Our relationship continued until his company transferred him to a different state.

I have had the pleasure of using the technique he used on me to deflower other virgin men. I may not be as big as my former lover, but before he taught me that technique, when ever I deflowered a virgin guys ass there was always pain. After I learned it there has not been.
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Posted by bigiowa7
2 years ago    Views: 1,817
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1 year ago
2 years ago
DAMN...would be so hot to play that way.
2 years ago
mmm loved it
2 years ago
2 years ago
Well Done!
2 years ago
realy good