Henry takes my virginity

My dad left when I was a high school  freshman. Thankfully his friend Henry stepped in and helped out. I was always very awkward and gym was very rough for me, not because I was skinny because I was actually very muscular but because I had a really tough time not staring at all the cock I seen in the locker room. I would get to excited and distracted I could barely function. At night all I could think about was sucking dick and spreading my legs for anyone who wanted to fuck me. I masturbated a LOT. 

When summer came around Henry took me to work with him to earn extra money and to help with the mountains of bills. Henry worked construction and we would have to take several busses and walk quite a way to get to the job site. On the way we stopped at a gas station to take a leak and I couldn’t stop myself from peeking at Henry’s cock. I was shocked, it was very very long and wrinkly, it literally completely filled his big hand, the stream was HUGE, I got rock hard and literally watched him piss the entire time, all the way up until he shook it a little and massaged the last few drops out and then hauled it back into his pants. 

I was hard as a rock, my heart was beating fast and my mouth was DRY. Finally when he stepped out and the door swung shut I was able to pee. I hurried after him but he now seemed distracted. That night when I got home his long wrinkly cock was all I could think about, I masturbated multiple times while thinking about sucking him and riding him. Henry was not a super good looking guy or anything, late 30’s, decent build from a lifetime of hard physical labor, jet black hair, big moustache, very hairy chest. 

The following weekend we were painting at the house and I was holding the ladder for him while he was painting the underside of the roof. It was hot and he was wearing loose cutoff jeans and I was able to look right up his shorts. He had HUGE hairless balls. Each was roughly the size of a lemon... I was mesmerized and beyond excited. Henry had moved in with us several weeks before and was currently sleeping in my room which had two twin beds. That night Henry asked me if I liked the way his dick looked. I started stammering and said I didn’t know and why would he ask. He said “I seen you staring at it, you know it’s true so don’t deny it.” I said I was sorry. 

It was fairly late and everyone was asleep and it was dark and thankful he couldn’t see me blushing. He had moved silently and was standing by the head of my bed, completely naked. Now his cock was much thicker and longer than it was in the bathroom at the gas station. It was dark but I could see it very well... it was literally only a few inches away! I was suddenly rock hard... he asked if I wanted to touch it. Instead of answering I reached out and wrapped my hand around the base... it was so thick I could not get my hand around it. 

I hefted it and was surprised by the weight of it. I slid a little closer and started sucking it, the head barely fit in my mouth... it was fat and spongy and soft but it was rapidly getting much longer and thicker and HARD. I swung my feet off the bed and sat and sucked as much of his now rock hard cock as I could get into my mouth which wasn’t much. I had both hands wrapped around his thick shaft and I was struggling to get the rest into my mouth. I started swirling my tongue around the head of his cock and then I would lick the long slit, actually sticking the very tip of my tongue into it. Henry let out a long moan which told me I was doing the right thing. 

The head of his cock was now very smooth and thin slippery  fluid was oozing out of it. At first I thought maybe he was peeing in my mouth but it was slippery and tasted like salty butter. I would lick and kiss and suck for a few minutes or until my jaw would start hurting and then I would gently stroke his full length with both of my hands until the fluid would flow down his shaft and then I would first lick it up and swallow it and then I would go back to sucking him. Roughly five minutes later he let out a fairly loud moan and suddenly my mouth was completely full of his cum. I had to come up off his dick to swallow it and when I did his second huge stream of come drenched my face. I quickly opened wide and now, taking only the fat head of his dick I swallowed the rest of his enormous load. In all he came for nearly a minute. 

It seems Henry suffered from hyperspermia and as a result he truly needed sex daily. Somehow I had came in my underwear while going down on him. For several weeks this became our routine where I would give him a nightly blowjob. Several times we would stop on the way to work and I would give him a blowjob in the gas station rest room. I started fantasizing about him actually fucking me. After awhile it was all I could think about. Finally I got my courage up and asked him if he might want to do something else with me. 

He said yes he wanted to but didn’t know if I was ready yet. I told him I was very ready. He said “Just so we are clear, you want me to fuck you right?” Blushing furiously I said yes I would love that. That night we snuck into the bathroom and he gave me an enema which was horribly humiliating but felt insanely good. After we went back to my bedroom and now with both of us fully naked and rock hard he had me lay back on my bed. He slid a pillow under my butt and then spread my legs wide and actually started licking and probing my hole. It tickled and actually really turned me on. 

I found myself thrusting my hole toward his mouth and hands. Several times I nearly came and Henry would stop wait a few minutes.. finally he pulled out a large tube of KY jelly and started massaging my hole with it. Gently he slid first one and then two big fingers into me. It was unlike anything I had ever felt before. I would often slide a finger inside myself while masturbating but his fingers were much longer and thicker and also he was using lube. Several times I nearly came from him fingering me and each time he would stop and wait. 

Finally he got himself into position between my legs and after applying a generous amount of lube on his long thick curved cock he gently pressed the head against my hole. After several minutes of gently rubbing the length of my slit , he entered me. I gasped and let out a small moan... it felt incredible but it HURT. I told him I thought we made a mistake and that I wanted him to stop. He said no and instead went much much deeper. Now he was nearly halfway inside me and the pain was enormous. 

I had lost my hard-on and now all I wanted was for him to get off me. Instead he started slowly thrusting back and forth, in and out of me. Incredibly after several minutes the pain was entirely gone and it was replaced with the most pleasure I had ever felt. Now I was rock hard and throbbing and moaning softly as Henry’s long thick cock went deeper and deeper inside me. Finally he was so deep inside of me it felt like he was up in my stomach, his huge balls were now draped over my ass. He asked me if I wanted him to stop and nearly panicked and said “No Henry please don’t stop. I love it.” 

He leaned in close and whispered “ Tell me you want me to fuck you or I will stop” I begged him “Henry please fuck me! I love it just please don’t stop!” And so he started going faster and faster and I felt a tingle  that started in the center of me and less than a minute later I had my first of many orgasms. By now he was fucking me in long hard deep thrusts with his pelvis slapping my ass every time he was completely inside me. I was now nearly euphoric and I was having one orgasm after another until I finally ejaculated so hard I nearly passed out.

We would end up making love nearly all night long and in every position imaginable. The next day I was so sore I could barely walk but I still wanted him again that night.