To my friend Steve in Austrailia... Sorry you had to wait so long.
This is the second story of the Lakeville Chronicles. The first story was titled "Because I like the View" and the next story will be called "Another Perspective" both of which should be able to be found in the "Rural" section of "Gay Male" at Nifty. You do not need to read these stories in any order unless noted in the preface.
You see; I live in a townhome complex on the edge of the lake. I chose the specific unit because of the view of the lake. I can relax after a hard day's work by watching the sunset on a huge deck that sits on top of the front third of the two car garage. If it is cold, the second third is an enclosed sun room in-between the deck and the long family room. I don't need two bedrooms, a family room and a living room, but the only other units that were available were court yard view. So I made the best of it and placed two twin beds and my second computer in the second bedroom and use it for overnight guests like my nephews that often visit over weekends.
All of the buildings have a court yard in-between the garages with a grassy area and flower beds that you share with one of your two next door neighbors. The split-level floor plan is efficient front to back. There are two doors in the back of the garage. One that leads to the couryard and the other leads directly to the kitchen convenient for carrying groceries. The front door leads to the living room and dining area as well as a stair case leading up to a landing where the family room is and continues up to the two bedrooms upstairs. The family room is where I put my large screen TV, entertainment system and new computer that I have networked to the older computer so my nephews can play video games when they come over.
I got lucky in that the unit that had the view of the lake I wanted was an end unit and therefore it also has a nice view of the forest that surrounds the complex on two sides. What I didn't expect when I started to live here was that I would end up watching more of the comings and goings of the boys who live next door then of the natural scenery. When I am home, and it is nice out; I practically live out there. I spend a lot of time outside reading and looking at the lake.
My neighbor is a divorcee with three boys; one who is almost never there. He is in his twenties, about my age, and I think he either has an apartment of his own, or he crashes at his friends a lot. Maybe he has a girlfriend, I don't know. I really don't know if he officially lives there or not.
The youngest looks around fifteen or so, and he normally stays indoors except for when he goes out to do the paper rout. He is a good boy, who seems for the most part to be studious, well groomed and obeys his mother. He is quite a contrast to the middle boy who is normally hanging around the front door with his friends because his mother doesn't let his friends into the house. The middle boy normally wears oversized pants, large tee shirts and his haircut is sort of between a bowl cut and a mohawk. I've seen him wear it teased up, but normally he wears it combed to one side. Through the thick walls between our appartments, I have often heard him arguing with his mother over simple issues that would be easier to just get it over with and do what she wants. He doesn't seem to fit into this town, much less this neighborhood, but I think he and his friends work on that point: Big-city-hoodlum wanna-bee's in a medium-sized rural lakeside township.
Even though the middle boy is normally unkempt and unruly, I have always had a strong attraction to him. I am not sure why. It isn't that I can tell that he has a nice body hidden under the oversized clothing, and it isn't charm. I don't even think it is his rebellious nature, but I used to find myself watching him every chance I would get. Maybe it was just a fascination about why he is the way he is, or what kind of equipment he is hiding under the oversized clothing. In hindsight I think it was more the mystery then anything else, both physically what was he like, and mentally how much was act and what was real.
I remember grilling some chicken in the shared courtyard earlier this summer. I was expecting my cousins in a while and started to cook when Jessy came out side to smoke a cigarette and wait for his friends. He sat on the porch sort of staring off, and sort of looking over at what I was doing. I started a conversation, "You going to the Offspring concert next week ?".
He looked at me, took a drag, and smiled before he spoke. "Does it look like I have enough money to go ?"
"heh, How much you need ?"
"um, I dunno...How much are the tickets ? " but before the conversation went any farther his friends arrived en masse. There was Mikey who was a big guy whom I wouldn't want to mess with especially in any alleys dark or otherwise, Tom who was a skinny guy who always looked like he was strung out on weed. Gary who was sort of a mysterious chap with dark hair and green eyes. He didn't show up as often as the other two. Gary didn't conform to the group totally either. Gary was always in concert T-shirts, and his jeans were faded, they weren't torn and eight sizes too big for him.
That day they were with a girl. She was dressed much like the guys with torn jeans and concert tee-shirt, and she had long sandy brown hair that she tied back in a loose pony tail. It was evident that she and Mikey were sort of an item.
After a while of the normal small talk about school, music and people that goes on in most high school cliques, Mikey took the girl by the hand and they walked into my neighbor's garage through the back door. There were some jokes back and forth about what kinds of stains they were about to leave in the back seat of my neighbor's car, and then Gary dared Tom to spy on them. Without hesitation Tom went into the garage and remained there for a time, then emerged with a silly grin. He then dared Gary who reluctantly went in. Tom then made some joke about Gary wanting to watch Mikey rather then Sheila. Jessy and Tom laughed a pretty hard about that concept.
I myself found Gary to be quite attractive, and was getting aroused thinking about the possibility that he might be in fact gay, when he emerged from the garage with a silly grin and the outline of a hard-on much like the one that Tom had when he came out. Tom and Gary in unison chided that it was Jessy's turn, but he refused. To me this seemed out of character. It may have been my imagination, but I think I could see a healthy bulge under the baggy jeans that Jessy had on. Thoughts entered my mind about Jessy possibly being gay himself. Was he turned on by Gary? I was so aroused by this aspect that I was embarrassed when Jessy called over, "Maybe you should go in for a peak!" They all laughed.
I was rescued by the arrival of my cousins.
I tried my best not to stare and give myself away, but it seemed that every time I went outside to do something, there Jessy would be. I didn't want to make it seem that I was avoiding him by going back inside, nor did I really want to leave, but staying became defiantly awkward over the week.
I started to find myself distracted at work, when driving and even when watching movies. To relieve the frustration, Thursday I borrowed some XXX rated videos from a friend and watched them one evening in the family room. I left the sound turned down, and set the CD jukebox to play several Yello CD's. I wasn't missing much of the plot-less dialogue of the smut on the TV, but what they lacked in plot, they more then made up for in beautiful young actors.
I laid on the couch watching the second act of the movie, and slowly jacked off as to not beat the actors to the punch. The second act of this tape went at a very nice long drawn out pace starting with kissing every inch of the body and oral sex. I had borrowed this tape before, but had resisted making a copy for myself, knowing that would never get any housework done if I had my own copy. I could sit staring at these young men all night for days on end.
Suddenly I was startled by Jessy standing at the arm-rest of the couch looking down at me. He was wearing his oversized 501 blue jeans with huge holes ripped in one knee, his hair was sort of messed up and he had a wild look in his eye. At first I thought I was imagining things and I looked at his slender body and his shoulders sticking out of the black oversized muscle shirt with the a cure emblem silk screened across the front of it. I don't even think I stopped jacking off it was so weird. I just looked at him and the video until he spoke.
"I caught you!"
I was still too stunned to speak. I could smell marijuana on him, but he looked like he was on something else; crystal-meth, Ecstasy or LSD, maybe a combination of all three. His normally beautiful eyes were big black holes with just a small ring blue around them. Staring into the darkness almost made me dizzy, like I was going to fall into them.
"Illegal videos!! Illegal faggot videos. I knew you wanted to suck my dick!"
I remained silent as Jessy stared at actor on the screen sucking the cock of another actor. I thought I could see the outline of a hard-on begin to appear in the leg of Jessy's jeans. "Yeah, that's what you are gonna do to me. Your gonna suck my cock or I'm tell the cops you have this queer under-aged porno!"
I was so stunned that I made no attempt to explain that the video not illegal, and you could purchase it at the adult bookstore down the street.
Jessy turned his torso towards my face. This was the first time that I could imagine what was hiding under the denim. It was like a weird dream. Being this close as I was at the angle he was standing I could see the bulge. I wanted to suck his cock, and was being ordered to do so. I hesitated a moment before reaching out and unbuttoning his oversized jeans that promptly dropped to the floor. His thick one quarter hard dick peaked out the leg of his black silken boxers that went half way down to his knee. My imagination was wrong, he was much larger and hanging in a different direction. My eyes grew large as I studied the girth of what was showing. "Yeah it's big... So, what are you waiting for ?!?!" Jessy said gruffly.
I looked up into his face and started peel his boxer's down as his cock started to go from one quarter hard to half hard. I tugged a bit harder and had trouble pulling them down because they were caught on his dick. I tugged once more and his cock swung back and forth as the shorts came down his relatively slender legs. His cock looked very heavy. I looked up at his firm stomach as he raised his shirt over his head, and then back down to his horse-like appendage that was starting to stand perpendicular to his body. I leaned forward and licked the underside of the enormous prick. I marveled as I watched it grow even larger. It seemed impossibly large on a skinny body. It looked obcenely engorged.
I took him into my mouth and reached out with my left hand and began to fondle his mostly hairless balls, and begin to pull on his cock with my right hand as I started to work as much of him into my mouth as I could. I couldn't believe that all this was happening. My mind raced; how was I going to suck on something that thick without my teeth hurting him? Would my jaw cramp before he came?
"You like that-- don't you faggot?" Jessy crooned.
I obediently answered with a "mmm mmm" and a slight nod of the head. I continued to work his cock as best as I could. It was so large that I could pull on it with both hands firmly wrapped around it, and still not get my mouth over the rest of it. I would have never imagined his dick would be this big. I would have thought that anyone with a prick that large would pass out from the lack of blood running to the brain, especially with someone with what appeared to be a 30 inch waist.
"you like that big cock... " Jessy almost moaned, then proudly added, "it's bigger then my older brother's. Hell, I once walked in on my mom with her boyfriend and I had to laugh because it is even bigger then his!"
I continued to suck. Still in shock at the huge surprise, amazed that I knew the secret that Jessy had been hiding all this time.
"Oh... God .... and it is almost twice as big as Mikey.... "
That I could believe. I have studied that bulge when he did some skate-board tricks. My mind raced: Would he be back for more later? God I hope so. What else would he want to do?
"Is it the biggest you have ever sucked?"
"mmm mmm" with a nod, but never taking my mouth off from his monster. Indeed, not only the biggest cock I had ever sucked, but bigger then I had ever seen in person. None of the guys I took showers with in High-School, none of the guys at camp, nor at the gym and not any of my lovers. I had seen photos and videos of a few cocks this big, but they were attached to huge men, most of which weren't all that attractive.
"aaaaaahhhhhhh... yeah... you are a really good cock sucker!"
Again, "mmm mmmm" with a nod. I take pride in being able to pleasure my lovers.
"ha ha... that is pretty funny... ooooohhhhh yeah.... don't stop"
I had no intention of stopping.
"you gonna drink all my cum ?"
Again, "mmm mmmm" with a nod.
Suddenly I felt the underside of his cock pulse, as my mouth filled with his hot creamy seed. I swallowed before the second, and third. His cum was sweet, and his moans which got louder and more frequent were mesmerizing. I couldn't keep up with him, and soon his semen was escaping my lips and trickling down his shaft to my hands and onto his balls. His moans continued to get louder and more insistent as he came long and hard. When he was finished I looked up and noticed that he was dividing his attention between me and the TV.
On the movie, the actors were starting to fuck doggie style.
"That is what I want now!" Jessy exclaimed. "You are gonna get down on all fours if you like it or not".
I wasn't sure about the size of his member inside of me, and wasn't worried about him going to the police, but in the heat of the moment I played along and obediently got down on all fours. My mind raced: He was ready to go again so soon? Would he try to keep up with the video? This video that was surely shot over several days? Could he cum as many times as several different actors over a few days all in the span of an evening?
He positioned himself behind me facing the TV and began to enter me much in the same manner as what was happening on the video. I was thankful that I had not been able to keep up because the semen acted as lubricant as he pushed mercilessly forward. I yelled, "aaaaaaaahhhhhhh!!"
Jessy slowed a bit, and crooned, "Oh, too much for you baby ?"
I managed to groan a "Yes!" as I started to masturbate myself to distract my ass from the pain I was feeling.
Even though it hurt, I wanted him in the worst way. Jessy continued to push forward till it was almost all the way in. He started to pump in time with the actors on the big screen. Luckily they were going at a really slow pace. Each stroke Jessy took he pulled out farther and went in deeper. As I got accustomed to his size he reached around my stomach and changed the angle of my torso, and ordered, "now, stop jacking off faggit!"
He held me in the same manner as the stud on the screen held his partner, and he sped up in time with them as well. It was so erotic feeling this stud inside of me, and watching my favorite video. To feel the same sensuous motions as I was watching on the big screen.. I felt his cock-head swell inside of me and his cock pulsing deeply within. I felt the heat of his cum, and the wonderful slickness that made his cock slide in and out easier. Though the actor in the video pulled his cock out and shot his load all over his partner, Jessy continued to pump harder and harder coaxing his orgasm to last longer. I felt him cum and cum, and soon felt his semen dripping from my stretched ass down to my balls.
The actors in the video traded sides as the stud who did the fucking laid on his back and his partner gently pushed his way in with the stud's knees pressed firmly to his chest. My head was spinning and I was almost limp as Jessy rolled me over pressed my knees to my chest and started to push his way back into me. After he was in all the way and took strokes fast er and faster, he stopped and lifted my legs pulling my ass off of the ground and resumed the quick pace just like the actors in the video. Faster and faster he went, It felt awesome even though my feet started to tingle like they were going asleep.
Normally when you submit to be penetrated, you know that you could be taken advantage of and trust them not to. You need to trust your partner, expect him to use some control. This was totally different for me. Jessy thought he was raping me. He used me to pleasure himself. He took every stroke with enthusiasm, like it would be his last. He drove it deep and fast with no regard to the consequences. In fact, the louder moaned or the louder I yelled, the more excited he became. He fucked and fucked and fucked.
I enjoyed watching his torso heave back and forth until he leaned forward balancing himself with his large hands on either side of my shoulders with my knees once again pinned to my chest. Faster and faster he went, even more virile then the expert actors on the big screen that I was now watching off and on upside-down. I alternated between watching the expression on his face, what ever of his body I could watch, and the TV.
His face would alternate between expressions of ecstasy, pain, astonishment and then ecstasy again. I could tell that he was getting a bit tired from the expressions and sweat on his face, but he showed no intension of slowing down. His tight butt pumped up and down as I felt his large member slide in and out. I gasped and moaned and gasped and groaned. The actors on the video uncoupled and shot cum over each other.
I felt him cum at the same time as the actors on the video. I wanted so much to jack off, but the way Jessy was holding my legs I could not. Jessy probably would have probably told me to stop like he did before anyway. I felt him cum again during the next act that was on the tape, and again when the tape rewound and ejected itself. Without the actors on the screen, he set his own merciless pace, in and out, the full length of his cock. Several times he withdrew completely before thrusting it back in all the way pressing his balls against my sore ass.
By this point I didn't know what to think. Though I felt a bit abused and a little numb, at the same time it felt wonderful. Never had I felt orgasms so intense. This last time with snow on the screen and his dick pulsing inside of me, I shot my load across our chests. It felt hot on my chest, and my dick felt like it was on fire. With each orgasm my ass clenched his huge cock and I looked into his face as his eyes grew large and his smile grew wider. I milked the last out of him with that fifth orgasm and he collapsed beside me dazed.
I laid there beside him thinking, trying to work this out in my head what I felt about it. I probably could have stopped him at any time, yet I did not.
Jessy was asleep. His face looked so innocent when he was asleep. I got a throw from the couch and covered his spent body. Looking at his face again when I covered him I could tell he was dreaming, and what ever it was about seemed to trouble him. He lightly rocked back and forth, and then calmed down and looked serene again.
I climbed the stairs to the upper level, and I realized that I was going to need to call in at work. There was no way that I was going to be able to sit all day at work tomorrow. I turned on the hot water and sat on the toilet while waiting for the water to get to a reasonable temperature. As I sat there I thought about Jessy, and about what had happened. Not only was Jessy so much bigger then I had imagined, his sex drive was unbelievable. He kept up with the video tape. Hell, he went beyond the video tape... that tape that is between ninty and one hundred and twenty minutes long.
I tried to remember if I had ever had an orgasm that had lasted that long, or that intense, and there wasn't a time. Not with the stimulation of penetrating or being penetrated by any lover, not manual or other manipulation. I wanted to feel that again, but where would that lead?
I climbed into the hot shower and laid down in the tub. I rested in the hot water for a while continuing to think about how it might be nice to do it again, and at the same time I wondered if a continued relationship would be destructive. While he wasn't the Marquis de Sade, I wasn't sure how long my body could take the inevitable abuse. I couldn't keep calling into work.
I stood up and finished the shower, dried off and went to bed.
Jessy was gone when I got up in the morning.
I didn't see Jessy outside for a week. I saw his friends come over, but he didn't come outside. His younger brother answered the door, spoke with them, and they left with disappointed looks.
I was stunned.
"I am so sorry..... Soooooo sorry."
"I know I had no right, and would like to make it up to you, but I am not sure I know how."
"um, I don't know what to say."
Jessy knelt before me and pressed his face into my crotch and said, "I will do for you what you did for me: suck your cock and you can fuck me. Fuck me as long and hard as you want. I won't tell anyone."
I reached down and helped him back to his feet, "No, only if you want to."
"Don't you want me? I must have really hurt you for you not want to ... " his voice trailed off.
"It is not that, I just couldn't do it to you knowing that you didn't really want it."
"But I raped you"
"Well.... Sorta you did, sorta you didn't"
"Lets go talk upstairs" I stopped in the kitchen and grabbed a bottle of wine and two glasses on the way up to the family room.
"The truth is, " I said pouring two glasses of Auslese, "the video wasn't illegal, I wasn't afraid of you calling anyone."
Jessy sat there stunned, and quietly reached for the glass of wine. "but then why did you let...." he trailed off.
"Yes, I was stunned.... Shocked even.... But your body was so breath-taking that I couldn't resist letting you ravage me."
Jessy sort of smiled, and took a sip from his glass. Nervously looked at the glass, and took another sip.
"...and you were a bit more the I bargained for, and bit more rough " I said sitting on the couch to the right of him.
"I am so sorry... " Jessy said as his smile faded.
"... but I liked it... and I forgive you, if you will forgive me"
Jessy looked confused, "Forgive you, for what ?"
"I let you believe that you had done something terribly wrong.... instead I let you sleep. As a result, I am sure you have been beating yourself up and remorseful all week. You haven't visited with your friends or even came outside."
"You have nothing to apologize for, especially after what I have done... I can't believe this..." Jessy took two or three swallows of his wine nervously. "You have always been so nice to me, and here I fuck up, I hurt you and... and I feel that I need to make it up to you somehow!" He said finishing off the glass and setting it on the lamp table beside him.
I took another sip of wine, and licked my lips. "Well... If you want to, you could make love to me. "
Jessy smiled, still looked a bit unsure or confused.
"why, didn't you like it ?" I taunted.
Jessy's beautiful blue eyes grew wide, "Fuck yeah! But ... I'm still getting over the fact that you aren't pissed as hell, and that you didn't bend me over at the first opportunity."
"It isn't that I don't want to make love to you, I do. It's that I want you to desire to be made love to more, but if that doesn't happen that that is okay too. I enjoyed our encounter and I'm glad your back"
Jessy poured us both a second glass and smiled a bit more. He handed me my glass with his left hand and said, "You don't know how relieved I am at hearing you say that." He reached out with his right hand and placed it on my left shoulder. "Got any videos ?"
I had returned all of the porno videos to my friend, all I had was some old movies that I really didn't want to see. I walked over to the computer popped in a CD with a large collection of mp3's, and win-amp stared. A couple of more clicks, and the visualization program was duplicated on the big-screen TV, and the sound was coming from the surround sound speakers. "sorry, I returned them mid week"
I moved back to the couch and sat back down. Jessy was a lot more relaxed now, looking much like an innocent young lad, smiling back at me. I took another swallow of wine and eased a bit closer to him. Jessy took the hint, and raised one leg high into the air, and rested it on back cushions of the low backed couch. I reached forward gently rubbing his thigh as his back slid down the arm-rest relaxing more into the couch. I massaged his leg as his crotch slowly eased its way toward me, and I swallowed the rest of my wine and placed it on the other end-table, as I started to grope the outline of his gargantuan erection as it strained against the buttons.
Jessy let out a low moan as my hands met their target. I gently massaged around the still growing outline as it made its way to his pelvis. My other hand swiftly made its way up his thigh, into the bottom of his shirt and I lightly ran my nails over his taught belly which made him twitch a bit from being tickled. I decided that his cock had struggled enough against the denim, and that it was time to free the monster. I continued to scratch his torso lightly with my left hand, as I ripped open the buttons with one tug of my right hand.
Jessy was wearing briefs this time, and without the aid of the denim, his prick easily escaped the waistband and started to straighten out toward his belly button. Actually, as it became fully erect, the cock-head was well past his belly button. I leaned forward and began to lick his almost hairless balls as I continued to tug his pants and underwear down. Jessy just made a gentle "mmm" sound as I started to lick his extremely long shaft. I tongued his cock in long sideways and diagonal licks crisscrossing the front of the huge shaft as if it were an ice-cream cone about to melt, but unlike ice-cream the more I licked the harder is cock became. When I reached the top, I paused to look at the engorged monsterous cock before I took the large head into my mouth and slowly impaled my face on it as deep as I could go without choking, and I stopped rubbing his legs and stomach and grasped his cock with both hands and began to gently pull at it at the same pace I bobbed my head up and down. Jessy moaned a bit louder, "Uhh God, you give such good head!"
As I worked on pleasuring Jessy, I felt his large hands against the back of my head. I prepared to have him force me to deep throat him, but instead he gently started to massage my scalp. I relaxed even more, and was able to take a bit more of him into my throat. Jessy breathed deeper and relaxed more too. "God, the best ever ... " Jessy said quietly in breathy tones. I lost all track of time as I alternately sucked and licked Jessy's huge cock. When I licked his cock it throbbed. It looked swollen or inflated somehow, like an obcene sex toy. The scalp massage made it feel almost like a dream as it made tingles go up and down my spine.
Suddenly Jessy breathed several short breaths, his cock head swelled up, the underside of his prick flexed, and my mouth begin to fill with his sweet cum. His cock spewed cum faster then I could swallow in what seemed to be one continuous stream. I swallowed what I could, and used what I couldn't as lubricant and continued to rub his moist cock more with my hands as I moved my tongue back, forth and around his cock. As he came, he started to breathe heavier and heavier. "Oh.... mmmm... Oh God!!" Jessy almost whimpered as his orgasm subsided.
I sat up, poured another glass of wine, and was pleased to find that it didn't taste sour after Jessy's sweet cum. Jessy was still breathing heavily, but he caught his breath long enough to say one word, "Unbelievable!" I stretched my neck, and moved my jaw from side to side to aid in recovery from the rigorous workout. I took off my shirt and looked at Jessy who looked so relaxed, like he had melted into the couch.
"Do you have enough left over to fuck me?" I said unfastening my pants.
Jesse sat up. "Are you sure? I don't want to hurt you again. I might loose control..."
As I stood up and let my pants fall to the floor. "I'll take that risk. I wasn't as sore as I thought I was going to be the first time when you were totally out of control, and I'm sure you will be a bit more careful." I said taking him by the hand and helping him to his feet. I led him up the stairs to the bedroom and to the king size bed. I pulled off his shirt as he sat on the edge.
Jessy said, "I wanna please you now," gently reaching to my erection. He fondled my balls gently, and didn't seem to know what to do. It was electric feeling his fingers touch me softly.
"Just make me cum the way you did the other day, that will please me the most"
Jessy smiled and crooned in a low voice, "I... think I can manage that..."
I reached into the drawer under the water bed and produced a bottle of lubricant and crawled into the center of the bed. Soon to be followed by Jessy on all fours. I laid on my back and started to use the lube as Jessy watched quietly and then knelt between my legs. When I was finished, he took the tube and smoothed a coat of lubricant on his long shaft while paying special attention to place more on the head. He then spoke softly, "Are you sure? I don't want to hurt you again."
I smiled, nodded, and tried to relax but ended up more bracing myself then relaxing. Jessy gently placed the well lubed cock at my entrance and gently pressed, but with his size gentle pressure wasn't going to be enough. He patiently held it there for a minute or two before pressing harder. I felt the cock head start to move forward, but it still didn't penetrate so I moved my hips and it moved forward some more, but the head was still not totally in. Jessy pushed a bit more and waited, and more yet it still didn't want to slide in. I reached out and felt his hardness between my legs, and it was slightly bent under the pressure. Jessy pushed once more, no harder then before, but this time the thrust drove it four inches in. I screamed, "Aaaaaahhhhh!"
"I'm sorry! Oh god, I'm sorry. I didn't want to hurt you! Shit!" Jessy started to pull back.
"It's okay, just don't move for a second" Jessy stopped.
Once again I shifted my hips side to side and arched my back adjusting the angle, and I tried to relax more. Then I said, "Gently." Jessy gently pushed forward, and I found that I wasn't ready as I thought I was. "Ooooh! Aaaahhh!"
"I'm sorry... I'm sorry" Jessy stopped again.
"It's not your fault. I'll be okay. Just a second"
I adjusted myself again, and pushed myself onto his shaft a bit, and I felt it slide into me. Jessy hummed, "Mmmmm"
I was sure I was ready now. "Gently," I said again softly.
Jessy carefully pushed forward, and there was barely any resistance. He slowly pulled back, and then pushed forward again deeper and deeper. "Oh god, your ass is so hot..." he moaned as he pulled back and pushed forward once more going deeper yet. He left it half way in and asked, "Are you okay?"
I nodded. He smiled, then pulled back again before pushing deeper yet. Though I doubt he had ever had anal sex before fucking me the week before, he seemed to know a bit about how to sense if his partner was ready to take on more of him. Suddenly he took his hand, still wet from lubricant, and grabbed my erection. He squeezed it tighter and tighter until his hand started to slide up my prick. He relaxed his hand and slid it back down my excited cock as he himself pulled back a couple of inches. The next time he squeezed my cock, he pushed forward driving himself deeper and deeper as his hand slid up my slippery shaft.
My head began to swim as a thousand things filled my head: did he learn this technique from the video that was playing last time he was here, or did I misjudge him and he has had anal sex before, or maybe he fondles the clitoris when he fucks women? Had he thought about this all week, as I had? Was Jessy bi, or gay? Could I handle giving him what he wants as often as he wants? Would he want to? Was this just sex for him, or would he want to be closer? Is it all the way in ? My God, what if it isn't?
Jessy pushed deeper and deeper. It seemed like he had been pulling back, and pushing deeper for an eternity before he made it all the way in and I felt the softness of his balls resting against my ass. Once at depth, he held it there, pushed as if he could go deeper, then relaxed over and over which really helped aid my body become accustomed to him, so did the intensely pleasurable hand job he was giving me that did not stop when he held his cock all the way inside of me.
I was almost startled when he pulled back two or three inches he had left it deep for so long. He was looking me squarely in the eye and judging me quite well. He could tell that it didn't hurt as he pushed it back in, and didn't waste time in the second stroke that he pulled back even further. He kept the same even rhythm and didn't very the depth for another long while, all the while he smiled down at me.
Then he buried it deep in me once more, let my cock go, placed a hand on each of my ass cheeks, squeezed them, and raised my ass about six inches off the bed. Then he started to pump again a bit faster as his smile grew. He licked his lips, sped up some more and started taking longer strokes. "Oh god.... your ass is soooo hot... " he said almost out of breath. "I wanted.... to tell.... you.... the first time....GOD!!! Better.... then..... Pussy!!!" He raised my ass even higher, and started taking strokes so long that only his dick head was left inside of me.
I could feel his cock begin to swell with the impending orgasm. That was all I could take. My own cock began to throb and swell. My balls started to draw closer to my shaft, and with my first ejaculation my sphincter clamped down on Jessy's dick just as it started to pulse vigorously filling me full of his lust. I shot semen across my chest and on my chin and on the bed above my left shoulder. Jessy continued to pump, partially hindered by my ass clenching him, and letting him go, but he kept taking as long strokes as my body would let him and his rhythm instinctively changed to match my orgasms.
We both came really hard, and when I was about to finish Jessy reached down grabbing my cock with his hand and he started to squeeze and masturbate me again, "Oh god.... I'm not done.. and I need to feel you.... you cum....more... " He started to work my cock like an expert as he continued pumping me. "I need... I knew the first time... last week... when you came... That I wanted.... Oh god... Oh.... Oh god.... Being in you.... when you cum... oh god... is the most intense.... " Though I thought I was spent but Jessy's added attention taught my body otherwise. I almost immediately shot a second volley of cum across my chest and I felt Jessy's orgasm that was beginning to slow, resume a vigorous pulsation.
When we finished, he gently lifted me some more and slowly withdrew. Then he set me back down as he rolled onto the bed beside me while he caught his breath.
"Are you okay ?" he asked softly. "I tried really hard not to hurt you."
My body was still tingling all over as I answered, "Oh god... I hope you liked that as much as I did... "
Jessy smiled real big and laid back down on the bed.
Suddenly I heard a thump behind me. Jessy had crawled out of his bedroom window, across a section of roof and jumped onto my balcony. He smiled and said, "I caught hell for not coming home last night... so.. tonight... for all they know I am asleep in my bed"
I smiled. Looking him up and down. He was so attractive in new blue 501 shorts, misfits muscle shirt and hair neatly combed as the night before.
"are you up to going inside for a bit ?" He asked eagerly.
I smiled, and got out of my chair and quietly walked inside. "I am sorry I got you in trouble"
"Shit, I come and go as I please. Sometimes I catch hell, other times they don't care. You see... It isn't about me, it is more about what kind of day my mom had at work then anything else, or how tight the budget is on any given day."
"So, whatcha got in mind ?"
"Um... " he raised his eyebrows, "I dunno... maybe doggie-style... "
I laughed. He could look so innocent while saying such things. I was in such a funny mood, I said, "Only of you can catch me" and I ran to the stairs and went up to the bedroom. Jessy was close behind me taking long strides and several stairs at a time. Jessy caught me just as I was about to jump for the bed, and he held me in sort of a bear hug from behind. I could feel his hard-on pressing against my ass as Jessy reached down with one hand and began to unzip my pants as he held me tightly with the other hand. I could also feel that he had removed his shirt on the stride for upstairs. I pressed my ass against his hardness and moved it back and forth pretending to be struggling against him, then I moved it up and down trying to excite him more. The hand that had unfastened my pants moved its way under my shirt and began to lightly tweak my nipple as the arm that was holding me firmly reached down and finished pulling my pants and underwear down.
Jessy jokingly pushed forward with his torso forcing me onto the bed on all fours, but not before I could grab at the top button of his jeans tugging them fully open. He wasn't wearing underwear and as his 501 shorts flew open his cock sprang out at a forty five degree angle from his stomach. I crawled across the bed as if I were trying to get away, but half way across the bed I felt Jessy's strong arm around my torso, and a cold trickle of lube between my ass cheeks. "Cold!" I exclaimed.
"Sorry... this should warm it up" Jessy said placing his long shaft between my buns. "Better ?" he crooned as he started to rub it back and forth between my buns greasing up his cock before changing the angle and pressing the oversized dick head against my sphincter.
This time my body didn't resist as much, partly from the workout the night before, partly because I could relax on account that knew I could trust him. He pushed, pushed a little harder and pulled back just as my ass gave way so that only the head went inside. Jessy then started to work it slowly in, this time he was a bit less serious and actually playful. He reached around me once more and started to squeeze at my cock as he started to penetrate me deeper. I'm sure that it took about half the time as the night before, and with less discomfort. By the time he worked it all the way in I was about ready to cum from the lubricated squeeze hand job much like the one from the night before.
Before long he was taking full strokes in and out of me, sometimes even withdrawing the head and all before plummeting the full length back into me till his balls rested firmly against my ass. It was ecstasy as I felt him start to cum I almost came myself. Like before, his orgasm was long and intense. Words fail to describe the warm feeling it gave me, it kept me on the edge of orgasm the whole time.
"I'm sorry I didn't get you off that time," Jessy said softly with his huge erection buried deep within me.
"I'm good for another round" I said as I started to slowly straighten my legs pulling Jessy closer to the bed. I then started to raise one leg to maneuver myself onto my back without totally withdrawing the extremely long prick from my ass. Jessy raised up a bit to let me move.
"Oh God... what are you doing ??!?" Jessy exclaimed has he rolled onto his back, as I maneuvered with him to keep him buried inside of me.
"Oh, you like that ?" I crooned as I squatted on top of him.
"That is so intense!"
I smiled down at him, and then started yet another maneuver in the squat position, completely rotating myself three hundred and sixty degrees around his cock.
"Oh God... if you do that again, I'm gonna fuck the shit out of you!"
"mmmm" I said tauntingly as I rotated again one hundred and eighty degrees.
Jessy started to arch his back and pump in and out of me as I squatted on top of his cock. I then lowered myself down onto it more and rode him some more. "Fuck yeah!" he growled.
"What was that ?" I said as I started to rotate back around so that I was facing him, all the while he was pushing in and out of me from below.
"Oh god... "
"It's a good thing you have such a long prick... it makes maneuvers like that almost easy."
"Oh yeah.... gives new meaning to 'sit on it and rotate' !!"
I leaned forward and positioned myself so that his gyrations could achieve the longest possible stroke without me being on the bottom. I felt his hand worm its way between my stomach and my thigh, and grab my cock. He started to squeeze and pull at it again. Suddenly he reached up and kissed me lightly on the lips.
"mmmm" I hummed as his hand begged my cock to cum.
"I had never imagined that sex with a guy would feel so good... "
"I had... never... imagined..... your dick... would.... be so.... BIG!!" I said out of breath.
My dick began to swell, which excited Jessy and he started to masturbate me faster. But instead of this bringing me closer to orgasm, the change of pace made it take even longer. My cock was so hard that my balls ached. Jessy started pumping in and out of me from below faster has he jacked off more determined then before. At this moment I wasn't sure if he was changing the pace to torture me into an even more intense orgasm, or if he was just plain excited. He pulled me close and kissed me again, this time our thoungues mingled. His mouth was minty fresh.
His thrusting became more pasionate. I broke the kiss and exclaimed "Oh god". I couldn't bear to have him change the pace again, so I started to lift myself up and push myself back down as much as I could at the pace he was going. Jessy started to meet my motion, as my orgasm neared.
Jessy was masturbating me about twice as fast has he fucked me when I came. I shot in his hand, all over his chest and onto the bed over his shoulder, and onto my own chest. Jessy started to cum during my third ejaculation. I felt the heat from within, and the smoother motion, as well as his cock pulsing and pulsing. Jessy started to make each stroke with such intensity, as if his life depended on making this orgasm the most intense and longest lasting ever. Each thrust of his cock, and squeeze of his hand performed as if it could be the last thing he did on this earth. I felt each pulse of his cock, as my own cock continued to orgasm. I leaned forward and resumed the kiss. Once again I tasted the mint on his passionate toungue.
I leaned back and coaxed our orgasm to last a bit longer. Our orgasm did last for a long while, then it subsided. Jessy left his cock inside of me and let go of my cock. I leaned forward and gently kissed him on the lips. I felt him pulse once or twice more within me, and my own cock pulsed once more in response. I laid on top of him, feeling this prolonged orgasm progress ever so slowly. We both sort of drifted off.
The next thing I knew, sunlight was shining into the room, and I felt the wet sensation of someone's lips around my cock, and a warm tongue licking the underside of my cock. For someone inexperienced in sucking cock, Jessy was doing a pretty good job.
"mmmm" I commented on the pleasurable wake up call. Jessy started to lick the underside of my dick and my balls, gently taking each one into his mouth one at a time, and then started to work his way back up my cock. I reached toward his leg, and groped my way up to his balls and then started to tug at his three-quarter hard dick. Not to masturbate him, but to indicate that I wanted him to sixty-nine. Jessy got the idea after moving a little, and me having to tug again several times until he was almost on top of me anyway.
I started to lick his cock, and his balls, but his length prevented me from sucking his cock while he sucked mine. I used saliva to squeeze-jerk him as I licked his balls, then got the naughty idea of tonguing his ass. I first just touched the tip of my tongue to the edge of his anus for just a second, then I waited. Then I touched it to the other edge for a moment, then I tapped it again and again lightly tracing a circle around his sphincter. I could tell this was turning him on, because he started to move up and down on my cock faster. I then lightly pressed my tongue against the edge and traced a complete circle around, this time without lifting my tongue. I repeated it again and again, each time pressing firmer with my tongue.
Jessy was groaning at this moment, and was about to make me cum. I firmly pressed my tongue against his anus as I started to jack him off faster. Instantly he shot semen across my chest and onto his chin as he sucked my cock. I pressed my tongue deeper and started to rotate it to try to intensify his orgasm, which seemed to work. Jessy groaned, "Ohh god... " And took a deep breath as I took my tongue out and pressed it back in.
"Oh god... Please tell me you'll fuck me.... " Jessy begged.
Without withdrawing my tongue, I let go of his cock, and started to push him into another position, and he rolled onto his back and pulled his knees to his chest as I continued to tongue his virgin hole. The lube was still laying there, and I silently coated my cock with one hand as I masturbated Jessy with the other, and continued to lick his ass. I placed the hand with I had used to apply the lubricant against his ass and pressed my thumb into him as I withdrew my tongue and knelt there between his legs. He looked so hot waiting for me to fuck him I didn't hesitate very long. I rotated my thumb a bit to apply the lube better inside of him, and pressed my dick against his anus as I withdrew my thumb. I gently pushed forward and the head went in without much difficulty.
I rested it there a moment before pushing deeper into him, his erection lifted off of his stomach as I pushed forward and he exhaled. I leaned forward not pushing any deeper, and started to kiss his jaw line, and pressed deeper as I worked my way around to his chin and down the other side of his jaw. Jessy reached around me with his arms and held my tightly, and one hand massaged it's way to my head and directed me to kiss him on the lips as I pushed deeper into him.
I reached between us with my lubricated hand and started to squeeze-jerk him as he had done me when I was in his position, and I started to fuck him faster and faster. His breathing became deeper as he shouted, "I'm gonna cum!!" without warning, his anus clamped down on my cock and he shot a healthy load of cum across his chest and face. I continued to pump even when has ass clenched me tightly, I started to cum before he was done, probably after his seventh or eighth , and that seemed to keep him going. He smiled and said between deep breaths, "I feel it... I feel it!!.... Pulsing!.... Oh yes!!" His hand met mine on his cock, and he started to take over jacking himself off to milk the remaining cum as I fucked him with long fast strokes.
I slowed down as our mutual orgasm started to wan, and between deep breaths I heard Jessy mutter, "Unbelievable" again and again.
Sometimes I would come home from work, and he would be waiting for me somewhere to surprise me, sometimes he would have done something nice like vacuum, dusting or putting away the dishes from the dish-washer, others he would be hiding somewhere necked and ready for sex. Coming home became a bit like Inspector Clueseau coming home to Kato, but instead of being attacked I was being kissed, taunted or unexpectedly fondled.
One time I remember starting to pre-rinse the dishes I left in the sink the night before, and suddenly I felt hands unfastening my pants and before I knew it Jessy was sucking my cock from under the kitchen sink. Once or twice he playfully acted out some rough sex where he threw me to the bed and ripped my clothing off before making passionate love to me, but it was nothing like the first time. Jessy wasn't out of control.
I still admire the boy next door, but now it isn't from afar. It is fall now, and something funny happened last week. I don't want to write about it just yet because I am not sure how it will all turn out.