Andrew's First Time


This erotic sex story published on Jan 1, 2010 was written by Richard Granite and is from our Gay erotic stories section.
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"My cock now strained at my pants as I thought back to my one night stand homosexual encounter with Ben."

“Come on, you have to have some kind of breakfast. The pan’s hot, I’m going to fix something for Andrew and me anyway, I might as well throw on a couple of eggs for you too.”

“Do you know how much fat is in an egg, Dad? I don’t think so.” Chloe picked up her book bag and threw the strap over her shoulder. “Besides, I told Ash that I’d meet her for a coffee at Jitters at 7:30.” I smiled inside. That was Chloe, always had somewhere to go, someone to see. A lot like her mother, I thought.

Just then the 6’ 2” frame of Andrew, her cousin walked in. It was obvious he’d just rolled out of bed. His red hair was pushed up on one side with apparent bed head. He was rubbing sleep from his eyes as he walked into the kitchen, but what really caught my eye were his shorts. He was wearing boxer brief underwear. They were made of a grey tee shirt material and came about half way down his thigh. Clearly through the material you could see the long thick bulge of his penis draping to the side. I immediately felt embarrassed for him, knowing that Chloe was seeing the same thing I was. I was about to say something to him, but he pulled out a chair and sat down and scooted his legs under the table.

I glanced over at Chloe to see if she had actually seen what I had. Her face was impassive, but she had her phone out and was punching some keys. “I am kind of hungry; I think I will have some eggs after all, Daddy.”

“What about Ashley?”

“I’m texting her now. I’ll hook up with her at school.” She continued to punch keys as she sat down in a chair and scooted to the table.

Suddenly, for some inexplicable reason, I had a lump in my throat and could not speak. I turned back to the stove. I cracked an egg and dropped it onto the skillet, my mind reeling. I was suddenly thinking some very horrible thoughts about my daughter. I knew that Chloe liked boys, although she always acted as if she didn’t like them, at least in front of me. We’d had the birds and bees chat a couple of years ago and were pretty open with each other about her feelings. Ever since her mother died, I knew that I would have to try to be her confidant. I had to try to take her mother’s place. I popped 4 slices of bread into the toaster and pushed the lever down.

Chloe looked over at Andrew, Looks like you slept well,” she giggled, commenting on his lop sided hairdo.

“Uh, yeah, great, actually.” Andrew sat continuing to rub his sleep swollen eyes. He had been living with us for 4 months now. Ever since the death of his parents, my sister and her husband, in an auto accident. He had fit right in with us, personality-wise, although sometimes a little quiet. He had a decent sense of humor and we often had laughed together over the years even before all of our tragic losses. I gingerly slid the spatula under and egg and gently rolled it to the opposing side.

Chloe picked up her phone again and flipped it open intently scrolling through her recently received texts. “Andrew would you mind getting us some orange juice?” she asked rather absent mindedly.

I cringed, “Hey, that’s okay I got it.” I turned from the stove.

Andrew was already up, “I’m right here, Craig. I’ll get it.” For some reason ever since moving in with us he’d gone to calling me by my first name only. He moved to the refrigerator and opened it. I glanced at Chloe and saw that she was looking over her phone and actually watching Andrew, his bulbous penis head mounding under his briefs. Although he didn’t look to be erect, it was obvious that his penis was exceptionally long and thick. He grabbed the juice, turned and stepped toward the table. Chloe’s eyes flickering between her phone and Andrew.

When we were through with breakfast, Chloe hugged me and pecked me on the cheek. “See you tonight Daddy,” she said as she headed out the door. I sipped my coffee as Andrew got up from the table and brought his dish to the sink.

“Don’t worry about those, I’ll get them,” I said. “You’re going to be late for school.”

“That’s okay, I’ll right myself a note,” he snickered.

“Uh hey, Andrew, I have to ask you something though. Could you please wear some shorts or something, at least, you know in front of Chloe.”

Andrew looked down, “Shit, Craig, I thought I had my shorts on this morning. Jeez, Shit, I’m sorry.” His reddening face giving away his bewilderment.

“Hey, Andrew, It’s not a big deal, really. We’re all family here. It’s just that Chloe is at a very……impressionable age. You know?”

Andrew stood two feet in front of me, his crotch at my eye level. I tried to keep eye contact with him. “Yes sir, I understand. I’m sorry, Craig. I’ll be more careful from now on.”

I smiled at him as I got up and put my coffee cup in the sink. I chuckled a little, “Yeah, besides, with all of the friends that Chloe has, I don’t need 150 girls over here all of the time, I’m already having enough trouble keeping the boys off of Chloe.”

After I finished up the dishes, I saw Andrew off to school and walked into the study to get some writing done. I sat down at the computer and pulled up my latest manuscript. I was in the middle of writing my third book. A series of books actually, sort of my own version of the great American novel. I sat and stared at the screen for a few minutes thinking of how to get going. My mind kept flashing back to breakfast. I worried about Chloe a little bit. I wasn’t sure what to do about that yet. I wondered about Andrew too. That huge fucking bulge in his shorts. Wow, He was going to be very popular with the ladies.

I felt my groin tighten a little at the vision in my mind of a beautiful young woman’s eyes as she saw and felt his erection for the first time. I felt more tightening in my pants as the thought continued. I clicked on the Internet icon on my screen. I really needed to relieve the ache in my groin before I could get anything done. I went to a gay porn website that I subscribed to. I belonged to a couple of them, a couple of hetero porn sites too. It’s just that this morning I wanted to fantasize about men. In particular, I wanted to fantasize about very well hung men getting together. I briefly thought back to the encounter with a man that I’d had about a year earlier. I hadn’t dated really, since Chloe’s mother died.

Consequently, I spent a fair amount of time on the Internet surfing porn for my sexual release. The ones I liked the best were always the ones where there was a well hung man pleasing a beautiful woman. I loved girls on girls too, but, by far, the sight of a huge penis sliding in and out of a petite woman was my favorite. I guess it just came naturally to me to start to fantasize about what it would be like to be that woman. I loved the thought of a man holding his penis to my lips. I would reach up and grab his cock and begin to gently lick and suck the head and look up into his eyes as they rolled back in enjoyment.

Eventually my fantasies turned to anal sex. I became fascinated with it. I even went so far as to purchase a vibrator from an online store. I remember waiting in anticipation for when it arrived. When it did, I could hardly wait for Chloe to go to school the next day. I spent a couple of hours with that vibrator and loved every minute of it. I thought that it might be uncomfortable to start with. So I slathered it with some lube I had purchased down at the drug store. To my surprise, it actually didn’t hurt at all, like I’d thought it might. It slid right into my anticipating ass. I fucked myself with it for a half an hour before I finally allowed myself to cum, when I did, it was extremely intense. Jet after jet of hot, sticky semen shot from my 7” cock as one hand pumped it, while the other violated my convulsing hole. From that moment on, my fantasies turned from that vibrator to having a man slide his huge erection into my awaiting anus. I spent countless hours with that vibrator as it had its way with my eager asshole, every minute wishing it was a guy like a porn star with his huge tool that was really pleasing me.

My cock now strained at my pants as I thought back to my one night stand with Ben, the only actual homosexual encounter I’d every really had. I reached down, pulled my belt loose and slid my pants and underwear off with one motion. I flipped my shirt to the side as I slid back into my chair and eagerly typed my password into the website log in. I gently caressed my rock hard cock as I maneuvered my way into the website. It didn’t take long to find what I was looking for. I clicked on the play button as a video loaded onto my screen. Immediately an image of a well endowed black male was sliding his big tool into a smaller man’s ass. The smaller man, a white male, in his twenties maybe, was lying on his back on a bed. His legs were spread wide as the ebony man held an ankle in each hand. He slid his large penis into the Caucasian man’s waiting ass. He slid it in and out rhythmically as the receiving man panted and moaned. I watched this for several minutes and began to get very worked up. My right hand was slowly stroking my cock while my other hand was down between my legs, the tip of my middle finger rubbing my anus. I placed each foot up on the desk, straddling my keyboard as my finger probed my sensitive hole.

Just then I thought I caught a glimpse of movement outside the window behind my computer monitor. I froze awkwardly and watched to see if I could tell what it was that moved. I saw nothing. I sat, frozen for a moment longer trying to regain the mood that had just been shocked from me so abruptly. Then my eyes refocused. That’s when I saw.

The movement I had seen did not come from outside my window….It had come from a reflection in the window. A reflection of something…or someone, off to my right and a few feet behind me! I leaped from my chair, my erection bobbing straight up in front of me. There in front of me, with eyes wide, stood Andrew. “Uh, jeez, Craig….I, Uh…”

I just stood there for a moment, unable to speak. I’d just been caught by my nephew watching and, yes…masturbating to gay pornography. “Shit, Andrew, I…Shit. Look, this isn’t what you think,” I said stupidly. It was exactly what he was thinking. Shit, how did I not hear him come in? I silently cursed myself as I stood, naked in front of Andrew, my erection beginning to soften.

“Look, Uncle Craig….”

Shit, He called me uncle Craig. Oh fuck, Chloe’s going to find out, Andrew will probably leave. Word about this is going to get out. Shit, shit.

“Look, Craig….I…Uh….Actually snuck in here…….to watch.”

That’s when I noticed something about him, something… I looked down slightly and noticed a large bulge in the front of his jeans. He took a step towards me, his eyes pleading. “I really didn’t make a mistake this morning. I knew that I wasn’t wearing anything over my underwear. I didn’t do it so Chloe would notice…I did it so you would.”

I looked him in his eyes, “Why did you think I would like that?” I was confused, wondering if he’d seen me do this before.

“I didn’t. I mean I don’t know. I guess I just wanted you to see me. I feel like a dumb ass, Craig, I’m sorry.” He turned his head as if he were going to leave.

I stepped forward, silently placing a hand upon his shoulder. He looked down at me, into my eyes. I slowly slid my other hand forward and gently caressed his erection through his jeans. My cock hardening again. I took him by the hand and silently led him to my bedroom. I turned and looked up into his eyes. “When did you know you were gay, Andrew?”

“I don’t know. Quite a while back I guess.”

“Do you have a boyfriend?”

“No, I’ve never….You know.”

“Wow.” I stepped back a pace. “Hey, look I don’t know if this is right. I mean, I actually like women. It’s just that I’ve been without one for so long. I mean what you saw…in there,” pointing in the direction of the study. “It’s lonely, you know?”

“I saw how you were touching yourself…Where you were touching yourself. I want to…..touch you there too.” He reached forward and gently caressed my engorged cock. It felt soooo good. I reached down myself and grabbed for his belt. I clumsily unbuckled it and unbuttoned his jeans, my hands shaking in anticipation. I dropped to my knees and pulled his pants down, his cock springing toward my face. It was truly immense. I’d never seen a penis that large before. Its bulbous head was as big as a child’s fist and it was really pink. Its incredibly long shaft leading to two walnut sized testicles nestled in a thick patch of orange pubic hair. It was hard as a rock, but still it seemed to be at half mast, so to speak. So large that it would not stand straight up, as my diamond hard penis was now doing.

I reached forward and held him in both of my hands, guiding his bright pink head to my lips. He peeled off his shirt and tossed it to the side as I gingerly licked the engorged head and slid my mouth over it. I managed to get a few inches of his thick, veined penis into my mouth and throat and hungrily began to work it in and out of my mouth as I pumped both of my hands up and down his shaft. He sighed deeply as I began to moan with wonton lust with his cock in my mouth. Andrew withdrew his penis and pushed me back onto the bed. He lay down on top of me, desperately grabbing for my penis. Clumsily his lips met mine and he pushed his tongue into my mouth. He worked his legs between mine and was thrusting his cock forward up and down my belly. It was obvious that he was very turned on and was loosing control of himself. As he lay on top of me, he clumsily thrust again and again. I could feel the heat of his cock against my cock and stomach as he slid it up and down.

He leaned back a bit and grabbed his cock with his hand quickly brought it up to my anus. I pushed my hand forward and stopped him from tearing me open with that huge stick. “Hey, slow down a bit. I’m going to need some lubrication before we go on.” I reached into my nightstand and pulled out the bottle of lube that I had used many times for my dildo. “Okay, Andrew, get on your knees here on the bed in front of me.” He positioned himself as I had asked and I reached forward with the bottle. I squirted a large dollop onto the head of his massive phallus. He just looked down and watched as I worked the slippery liquid up and down his thick shaft, my fingers barely touching as they wrapped around his girth. I began to moan softly. I wanted this dick inside of me soooo badly right then. I whimpered slightly as I felt it lurch in my hand. “Before we do this, I have to…you know, get ready a little bit. Think you can wait?”

He slowly nodded as I lay back on the bed. I spread my legs wide and brought my lube soaked hands to my anus. First I slowly, worked a finger into my little hole, then two. He watched, wide eyed as the slippery fingers of both hands were probing, spreading my hole wide. My eyes rolled back as I pulled my hole open a little wider. Andrew’s cock throbbed again as he watch me ready my sensitive hole for his phallus. I didn’t say a word as he slowly moved toward me. I held my hole wide as he pushed the head against it. He slid it up and down against my awaiting ass, his shaft glistening with the slippery liquid. Then he slowly pushed his head into me. I gasped as my fingers let go and felt his thick shaft as it slowly pushed into me. I looked down and saw my hard penis dripping a stream of clear liquid onto my belly.

He slowly withdrew and pushed again, his abs flexing as he was slowly working more of his fat stick into me. He had slid about half of his length into me when I felt a sharp pain up in my abdomen. I winced slightly as he pushed the huge head of his dick against the internal obstacle. He withdrew and thrust again. My mind reeling as I felt his hugeness violate me. He pushed in even further this time before withdrawing and pushing again. I cried out as he pushed even more into me this time. I began to whimper incoherently as he thrust again and again, my hands to each side of me, tightly gripping the bed, bracing myself against each thrust.

Andrew then lost his control, for he thrust hard and deeply into me, withdrew only the slightest and thrust again, his balls audibly slapping against my upturned ass. “Oh fuck,” was all Andrew could say as he thrust the entire length of his massive phallus into my eager anus, sweat glistening on his flexing abs and dripping from his upper lip as his cock began to erupt. He began to grind his cock into me, trying vainly trying to push even more of himself into me. I had not even touched my own cock during all of this as I didn’t want to spoil it by cumming too soon and I continued to tightly grip the bed to either side of me, but now it was too late, I could no longer hold myself back. As Andrew’s cock spewed his hot sperm into me my own cock jerked and erupted with the longest, largest jet of semen I’d ever seen. It splashed onto my face and into my waiting mouth.

The second jet was equally as large and wet as the first. Jet after jet of semen doused my belly, chest and face. I could only groan as I watched my penis empty its seed. Andrew then lay forward on top of me, breathing heavily. After some minutes he leaned back, withdrew and went into the bathroom. I could see a reflection from my mirrored closet doors of myself, my violated anus oozing a stream of Andrew’s white semen.

Andrew emerged from the bathroom and stood, looking at me lying on my bed, legs still spread and basking in the afterglow of my incredible orgasm, his penis hanging long and thick between his legs. “I’m sorry if I’ve messed something up with you Craig.”

“No Andrew, it’s actually me that should feel guilty.”

“Well don’t Craig. I’ve fantasized about it for a long time. I can’t believe that I’ve finally had it come true.” He walked over to me as I propped myself up on one elbow. He look down at me and into my eyes, “and I’ve got to be honest with you, I think that I want it to happen again.

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