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Alec - A really good friend of mine
🕑 Added 2024-08-16 04:24:35 +0000 UTCJessie was a friend. He was the product of divorce, which, when we met in 1988 in 9th grade, it was still pretty taboo to be divorced. There was always some sort of cover story of why the dad was out of the picture. In Jessie’s case, he couldn’t really hide it. He was always spending half his time with his dad and the other half here in Rhode Island with his mom.
I was always excited when he would be back in town. He always had wild stories. Most of them involved girls he had been intimate with in one way or another. I never had any new stories for him. I learned almost everything there was to know about s-e-x from Jessie and his stories.
In the summer of 1991, Jessie appeared at the Scoop Ice Cream Parlor, where I was working at the shore.
“Alec, my main man,” Jessie beamed as he walked up to the surprisingly dead counter. This time of year, we usually have a line twenty customers long constantly, but it rained all week, and today was threatening to rain, too.
“Woah, Jessie, I didn’t know you were in town. I thought you’d be back in Wisconsin doing… some dumb blonde named Tiffany or April or something,” I laughed, putting my thumbs in the strings of my apron and then leaning my lanky body over the counter, holding myself up on my elbows.
“I’m spending the summer with Mom since I won’t be here for school in the fall,” he said.
“Wait, what? Why not?” I stood back up straight. I felt like I had just been punched in the gut.
“I graduated early. With all the different classes I’ve taken between here and there, I had enough credits to graduate early. I’m going to be starting college in Boston in the fall. I thought you knew that,” he crossed his arms, which were bulging with muscles he didn’t have the last time I saw him.
“Well, damn, this is the first I’m hearing of it,” I felt suddenly overcome with emotion and had to do my best not to cry. If Jessie were going to college this fall, I wouldn’t see him again after this summer.
“Don’t worry, I’ll be back every summer until I’m done with college,” he laughed. “My grandmother, my mom’s mother, is paying for college, so I’m expected to be here all summer every summer to kiss her ass,” he shrugged, tapping his fingers on the counter and reading the menu.
“Well, shit, I’m glad you’re back for the summer at least,” I confessed. “Can I get you a cone? My treat?”
He bobbed his head and smiled wide, brushing his medium-length hair out of his eyes and tucking it behind his ear. The contrast of his dark brown hair on his pale white skin was always eye-catching, but now that his hair has grown out, his cheekbones really pop, and his dark red lips almost make him look like he’s wearing lipstick, but his lips have always been dark red like that. "Yeah, I’m looking for something wild, like…” He continued to scan the menu and drum a rhythm on the counter that sounded oddly like AC/DC’s Thunderstruck. " Ooh, give me Death By Chocolate; that sounds delicious,” he chuckled.
He always got the Death By Chocolate, but it still made me smile somehow. I gave him a triple-scoop ice cream cone, which was already dripping from the heat by the time I handed it to him. I watch him use his unusually long tongue to lap up the drops quick enough that not a single one hit his hand that held the cone in a tight grip. I couldn’t help but smile; something about the way he did that was oddly…um…I couldn’t stop watching.
He was such an entertaining guy and possibly my only real friend. Sure, I had a group of friends in school, mostly because I am on the lacrosse team, but that’s mostly because my parents insist I play sports. At the end of the day, I don’t spend much time out of my house unless I’m working, at a meet, or Jessie is in town. When he’s in town he forces me to step out of my comfort zone and do things that are fun that I wouldn’t do if he didn’t push me to. I always have fun too, but then he’s gone for a few months, and I’m right back to being a hermit and happy to be.
“What time do you close up?” he asked, taking a massive bite of the ice cream, the corners of his mouth coated in dark chocolate.
“I am supposed to close at 9,” I told him, hunching over the counter lazily, shaking my ass to stretch out my lower back as I did.
He licked his lips and smiled, “Perfect, I’ll swing back through and…scoop you up,” he laughed.
Over the next five hours, I made sure to clean the shop as quickly and as often as I could. I wanted it ready to lock up and walk out as soon as the clock struck nine so I could go hang out with Jessie. I already called my parents to let them know I would be out late and probably crashing at Jessie’s house, so they didn’t need to wait up.
At the stroke of nine, I pulled the gate down over the big service window, rinsed the last of the scoops, and put away the last open toppings. By 9:02, I was walking out the door and locking up.
“Al,” I heard Jessie running up behind me.
He wrapped his arms around my waist, lifting me off the ground and giving me a bear hug.
“Ooof, ungh, put me down,” I protested while also laughing at his shenanigans.
He dropped me back onto my feet. “Listen, I met these girls on the beach earlier; they’re having a party at a house just up the way. These girls are prime for the picking.”
I groaned and rolled my eyes. I was hoping to just hang out with Jessie tonight, not watch him try to get laid at a house party filled with rich girls visiting for the summer.
“Come on, Al, maybe you can finally lose your virginity,” he elbowed me in my side.
“Uhhhh…” I shook my head no, “I guess,” I ran my fingers through my short hair, trying to fluff out the hat hair from my visor.
He grabbed my shoulders hard, rubbing my muscles, “That’s the spirit!”
We went off to a house party at one of the rental properties that mostly sits empty during the winter. It was a huge party. Beer kegs are available in three different locations on the property. Heaven forbid you had to walk more than twenty feet to refill your cup.
As predicted, ten minutes into the house, some beautiful blonde girl needed Jessie’s attention, pulling him away with the promise to return him in a minute, but then I didn’t see him for more than an hour. Annoyed, I was about to leave and head home, but then he appeared out of nowhere, grabbing my wrist, which slipped into a handhold.
“You’re leaving?” He asked, the smell of beer on his breath and remnants of red lipstick on his already vibrant pencil-thin lips.
“Yeah, I’ve had enough,” I held up my empty cup and then tossed it into the trash across the room, barely making it in.
He looked around the room, looking for someone, then bit his lower lip, “Yeah, you know what, me too. Let's get out of here. Do you want to crash with me? I know you’re parents would kill you if they found out you had a beer or kissed a girl,” he chuckled. “Wait, did you kiss a girl?”
I shook my head, unable to resist smiling at his silliness. “No, but yeah, let's get out of here.”
We stumbled back to his grandmother's home. A massive eight-bedroom colonial home with a three-car garage and guest house. His mother lives in the main house, and they let Jessie move into the guest house when he got into rock and roll, what his grandmother calls “the devil's music,” but as long as he still went to church on Sundays, he could live peacefully in the guest house this summer. After all, he was going off to college in the fall, so he should be able to live on his own.
The guest house smelled like Jessie. It was a bit messy, with his dirty clothes strewn everywhere. The clean clothes were still folded in his massive open duffel bag on the floor.
“Take your shoes off; we’re not animals,” he half-joked, kicking his off and they flung halfway across the room.
I took my shoes off and then my Scoop uniform t-shirt off, tossing it into an antique leather armchair in the corner of the bedroom.
Jessie eyeballed my chest, “Dang Alec, looks like lacrosse has been doing you some favors,” he laughed, setting a small wooden box on the coffee table.
“What’s that?” I asked, uncomfortable with the compliment.
“You smoke?” He raised an eyebrow like he had assumed everyone did.
“I…I can’t say that I have,” I stammered.
“You want to?” He started rolling a joint.
Maybe it was the booze from the party earlier or just any excuse to look cool in front of Jessie, but I just shrugged, “Sure, why not?”
He smiled and rolled a joint. His long tongue went to work to wet the paper to hold it together. Then he lit it up and took a long drag like it was something he had been missing his entire life. Then he passed it to me.
I took a quick hit and tried to pass it back to him. His smirk curled hard on one side of his fair-skinned face, and his cheek rippled several times to accommodate his grin.
“No, take a real hit, man, really inhale and get it into your lungs,” he said.
I did as I was told.
“Now, hold it,” he insisted.
I did, but after a few seconds I couldn’t hold it any longer and started coughing out the smoke. It sent me into a coughing fit, like I had swallowed water down the wrong tube. Jessie laughed at me, taking back the joint and took a long hit for himself.
“That’s the normal reaction, don’t worry, it’s a good thing. In a minute, you’ll feel it in a way I never can again,” he said ominously.
He was right, though. Once I was done coughing, I felt a bit dizzy. I wasn’t sure if that was the effects of the weed or the lack of oxygen from my coughing, but…I kinda liked it. We passed the rest of the joint back and forth, me coughing less and less between each hit. The effects were getting better and better, though.
The heat in the room was horrible, “do you have a fan or something?”
“No, this old carriage house was turned into a guest house in the late fifties; they didn’t outfit it with enough electricity for anything but lights and the stereo, and I’m not turning off the stereo,” he pulled off his tank top, leaning back into the leather armchair. The dim lighting accented his glistening chest. I hadn’t seen him without a shirt since last fall. He somehow lost all of his baby fat, and it turned out that he had muscles underneath. The sweat only made his muscles look bigger as he rolled another joint. He lit the joint and passed it to me. I inhaled, trying to hold it in while watching Jessie as he quickly unbuttoned his jeans, thrusting his hips up, his shoulders pressed firmly into the back of the chair and pushed the jeans down to his ankles. His white briefs are now the only remaining item of clothing on him.
I inhaled the majority of the last of this joint before passing it back to him and shucking my jeans to follow his lead. The quick movement made me realize how quickly the weed went to my head, and it made me giggle as the world around me took a second to stop swirling.
His eyes traveled over my body, saying nothing. I don’t know why, but being eyeballed by him made me feel warm inside.
I strut across the room in my underwear. Maybe I was flexing the body lacrosse built, but I was really just trying to shake the weird feeling I was getting from looking at Jessie in his underwear. I don’t know what it is. All the guys on the lacrosse team, myself included, wear the exact same white briefs Jessie is wearing, but somehow, on him, it’s like…doing something to me. Almost like what the guys describe feeling when they see their girls in only a bra, but…that can’t be right. I dove into Jessie’s bed face first.
He laughed, “You alright?”
I mumbled into the blanket, “Yeah, I’m just…mmm…feeling it now,” I chuckled.
I felt the mattress shake as he climbed onto the bed on the other side, his head falling onto the pillow. “Man, I was really hoping Allison would put out tonight.”
I popped my head up, looking up his hairy leg to the pouch of his briefs, a hint of pubic hair sticking out of the elastic of the leg hole, the mound in his underwear looking bigger than mine, his skin glowing with sweat from the heat as his chest rose and fell with each breath. “I thought she did; you were gone a long time.”
He huffed, “Nah, she just gave me blue balls,” he chuckled, then cupped and shook his package, which sent my blood flowing to my own package for some reason.
I swallowed hard, the weed sucking the moisture out of my mouth, “What do you mean?”
He chuckled, “You know, blue balls?”
I had heard other guys describe this phenomenon, but I had never seen it, “You mean, your balls are blue?” I stared hard at his white briefs, trying to see a discoloration of any sort through the thin, worn fabric.
He laughed, “No, it’s like she got me all turned on, acted like she was going to let me fuck her, but then…didn’t go through with it at the last second. Now my balls ache from being teased so much,” he massaged his balls from outside his underwear. Pulling down the waistband a little with each rub, more of his happy trail showing and the top of his bush peeking out as he rubbed up and down on himself. He was looking up at the ceiling as he explained this all to me.
“I haven’t had blue balls,” I chuckled.
He popped up his head, “You must jerk off a lot.”
I giggled, “Oh man, you have no idea,” I heard myself admit before I could process what I was saying.
He laughed, “Do you want to jerk off?”
I looked up at him, “Wha…what do you mean?” I felt my heart start beating fast.
“I need to jerk off,” he sat up on his elbows, his abs crunching, “do you want to jerk off with me?”
My eyes went huge; I didn’t know what to say. Jessie was the only guy I’ve ever told I even jerk off, something I’m deeply ashamed of, and he wants to do it together?
“You’ve jerked off with your other friends before, right?” He sat up, crossing his legs, the bulge in his underwear looking noticeably bigger than it did minutes ago.
“I, um, I haven’t,” I swallowed hard, feeling my dick get hard underneath me, pressing into the mattress.
“Really? I thought all of you jocks…” he made a hand gesture that made it look like he was stroking a giant invisible dick.
I shook my head slowly. “no.”
“Wow, umm…” he looked around, his palms now running up and down his thighs slowly, “Do you want to?”
“I…don’t…know how,” I said nervously.
He smiled at me, “I’ll show you if you want.”
I nodded quickly but nervously.
“Get up here, lay on your back,” he said, patting the pillow like you would to get the attention of a puppy, and just like a puppy, I hustled to get into the spot designated for me.
I rolled onto my back, quickly covering my full erection with my hands.
He shifted himself between my legs, his own briefs barely hiding his erection. He confidently spread my legs apart and shimmied himself closer to my crotch, rubbing his hands up my legs until they hit my hands, then pulled my hands away from my crotch, revealing how hard I am to him and started to shiver; I was so excited my body couldn’t process the adrenaline.
He took it a step further and started to rub my erection through my underwear. I had never been touched there by anyone before. The slight touch of his hand, even with the cotton fabric between us, was sensational! Like a miniature atomic bomb went off in my brain, smack dab in the middle of the pleasure zone.
“Mmm,” my torso instinctively lurched forward, my legs spread to allow him to continue as my shoulders fell back onto the mattress.
He snickered at my reaction, but I didn’t feel nervous anymore. Something had taken over my body, and I just needed him to continue.
He reached for the waistband of my underwear, his fingers slipping under the elastic, touching my lower abdomen, skin that no one had ever touched but me, and I groaned. My cock sprang free as he continued to pull my briefs down and let the waistband rest under my balls the same way I had done many times before when I played with myself in private. I was so hard my dick actually hurt. He knew it, too. Grinning at me, he quickly wrapped his hand around my 6” cut cock; the feeling had my abs crunching tight again and again my torso hopped up off the bed as I inhaled sharply. He started stroking me slowly; it felt so good; there was no way I was going to last.
I held my hands up, “Wait, I uh…” then I felt my balls tighten; I couldn’t stop it, I unloaded a huge shot of cum. It rocketed out and hit my chest, then rope after rope splattered onto my abs as Jessie continued to stroke me through the most amazing orgasm of my life. My body twitched and tremored, the pleasure running through my entire body. I could’ve died a happy man at that moment, but just as quickly as it started…it was over.
I felt really embarrassed by all of it and didn’t know what to do. Thankfully Jessie didn’t laugh at me or get grossed out that he had my cum all over his hand. Instead, He quickly pulled down his briefs with his clean hand, revealing his cut cock, which was at least an inch bigger and thicker than mine, and to my horror, used his cum covered hand to stroke himself.
“Ugh, nooo,” I mumbled in disgust.
He chuckled, “It’s like using lube,” he said with a warming sense of gratification in his voice and in his eyes.
I didn’t know what he meant by that, but it was pretty gross either way. Though watching him enjoy it as he stroked his cum slicked cock was a sight to behold. He leaned back on his left hand, his ass on his feet, as he flexed his abs and stroked himself with his right hand. He stroked for only a few long minutes, and I watched with my eyes glued to the show. My own cum got watery and pooled in my abs, but I watched with bated breath. I resisted the urge to reach out and touch him. I don’t know what the rules are in this situation, but when I saw his hairy balls pull up tight to his cock I knew he was about to shoot.
Jessie groaned and took a sharp breath, then the base of his cock twitched a nanosecond before the first rope of his cum shot out onto his abs, followed by several others. I was in awe; I had never seen anything like this. It was amazing. “Oh wow,” I heard myself say, which got a weak chuckle out of him as he dropped from his hand to his elbow on the mattress, huffing out of breath and slowly squeezing the last of his cum out of his cock. I had never produced a load that big; I was impressed and jealous.
After a few seconds, maybe a minute of catching his breath, he slowly got up and grabbed a dirty t-shirt, using it to wipe the cum off his abs, then his hands, then his cock. He held it out for me to use to clean up. I took it; it was visibly coated in his cum. I tried my best to find a dry spot and started wiping my body, but I felt wet spots of the shirt touch dry parts of my chest as I did, the smell of Jessie’s cum and hints of his body oder wafting from the dirty shirt and I knew I was getting more dirty than clean at this point, but I needed to dry off. The hardest part was drying off my now soft penis without getting his cum on me as I did.
Once dry, I tucked myself back into my underwear; he already had his dick tucked away. I held out the T-shirt. He took it and dropped it on a pile of dirty clothes, wiping what was probably both of our cum onto the hip of his underwear like it was no big deal. He quickly sat back in the leather chair and started rolling another joint. He smiled at me. I hadn’t really moved in minutes; I was still recovering and still trying to have a clear thought. He cocked an eyebrow up at me, his grin pulling to one corner of his mouth, “Felt good, huh?”
I huffed, “Yeah, I’ve never…felt anything that good before.”
He grinned, “I’m surprised; I just assumed you were into that. I’ve done it with a couple of my friends.” He let those words bounce around in my head while he licks and then lights his joint.
We smoked and had some deep talk about the future. This led to the question of whether we thought Back To The Future Part II was going to be our future, with flying cars and all that. That went down the spiral of the legitimacy of the BTTF time travel theory. Eventually, we both got into bed and fell asleep.
The next morning, I woke up groggy, and the events of the night came flooding back to me. I looked over at Jessie, his longer dark brown hair covering his face, his thin body on full display as it was too hot to sleep above the covers. I found myself staring at his morning wood, stretching the fabric of his white briefs, the elastic on the leg holes, and around his waist, doing that thing that happens after wearing them for 24 hours straight, and they just don’t fit snugly anymore. The thoughts and feelings running through my mind both grossed me out, and… a part of me, a very strange part of me, wanted to reach out and touch it. I didn’t get to touch him last night as he touched me; the idea was making my heart race, and I felt it in the pounding headache that came as a consequence of last night's partying.
I shook off the thoughts and chose to get up. I quietly got dressed and headed back home to shower and change before heading off to work. After all the sweating yesterday, I smelled pretty ripe, and I won’t make tips at work if I smell bad while looking like I haven’t showered all week, even though I showered yesterday morning.
My day went as usual. It was sunny out, so we had customers lined up from open until close. Jessie didn’t stop by at all, but I was okay with that; I needed a good night's sleep.
When Friday rolled around, Jessie popped into the customer window during a slow period. I popped out and took a break so we could walk down the shore a bit.
“You’re still alive? I was beginning to think you died on me,” I joked.
He nodded his head, “Yeah, sorry about that. My grandmother on my Dad’s side passed away, so I had to pack up my shit and book a flight; I have to cut the summer short and go back home to help him with things.” Jessie picked up a seashell and examined it like some sort of dinosaur fossil, then hurled it back into the ocean.
“Damn, that sucks, I’m sorry. Were you close?” I asked, feeling like a dick for my joke.
He took a deep breath. "It's not like I am with my grandmother here, but she was nicer,” he smiled, hiding his pain.
“When will you be back?” I asked, more for me than for him.
“I probably won’t be. It’s expensive to fly back and forth, and my Mom and Grandma teamed up and agreed it would be best if I spent this time with my dad.” He shrugged.
“Shit, well…that really sucks,” I felt a pang of disappointment.
We continued to walk a bit and then turned back, not saying much. I gave him a hug and told him to reach out if he needed anything, even though I knew he wouldn’t.
I spent the rest of the summer avoiding parties. I was saving up for a car, so I put in as many hours as I could at The Scoop and then would go straight home after. On some occasions, I would meet up with the guys from the lacrosse team in the park and play a bit, but we could never get enough guys together to play a real game. It was still fun, though.
School started in the fall, and it was classes, sports, homework, masturbation, and sleep on a vicious loop. Which had really been my average day all of high school, but now the masturbation was more interesting because I now knew what it was like to be touched by someone else. Sure, that someone else was my best friend, Jessie, but…it still felt awesome, and I couldn’t stop fantasizing about doing it again. Trust me, I tried.
Call me naive, but I hadn’t really considered doing more than repeating that exact same experience with Jessie. Honestly, I didn’t think there was more to be considered. I was shocked to find out guys jerked off together. I started wondering if the other guys on my team jerked off together. I know a lot of them had girlfriends and claimed to be having regular sex with them, but the majority of us were single, so…did that mean they were doing what Jessie and I did? The images of the toned guys I had seen in the showers after practice jerking each other off seemed to creep more than once into my head while I jerked off, only intensifying my orgasm.
Oddly enough, as soon as I would unload, the mental images were gone, and the idea of even touching another guy was beyond…well, gross.
When Christmas break rolled around, I knew Jessie would be coming back to visit his mom after finishing his first semester of college. I was a little worried he would come back and tell me he had a girlfriend, or worse, wouldn’t come back at all. As soon as he was back in town, though, he stopped over with a plate of cookies from his mom to my family as a Christmas gift.
He looked different. His hair had been shaggy before, but now it was almost shoulder length and styled, so he looked more like the kind of guy you expect to see at a fancy college wearing a turtleneck and a tweed jacket with arm patches. He told me he couldn’t stay long because he had to go shopping with his grandmother, but he wanted to hang out tonight. He warned me a lot of his extended family was in town, so we would have to hang out with his cousins, but I didn’t care.
That night, I made my way to his grandmother's home, which was all decked out in colored Christmas lights. His family was throwing a huge party, and by the time I made it over, all the adults were already smashed, and the little kids were running around with candy cane smeared all over their faces. Jessie and his cousins were all hanging out in the guest house in a cloud of smoke. They panicked when I opened the door, thinking I was one of their parents. I’ve never seen a group of mostly strangers so happy to see me at once when they realized it was me.
We all hung out, smoking weed that his cousin Alister brought with him from California, and it was pretty amazing. I hadn’t smoked since the last time I hung out with Jessie, so maybe it was my newbie lungs, but man, I never found a ficus plant more interesting than I did in that moment.
At some point, the cousins started disappearing; I assumed they were heading back to the main house to go to bed.
“Alec, are you ok?” I felt Jessie tap my shoulder, grabbing my attention.
“Oh, yeah, what’s up?” I smiled goofily.
He chuckled, “I’m going to walk Jackie back to the house. Do you want to come with us or wait here?”
“I’m going to wait here,” I settled into the leather high back chair.
He grinned, “Ok, I’ll be back in a few.”
He and Jackie walked out of the guest house, and I don’t know how long he was gone, but it felt like only seconds before he was tapping me on the shoulder again, “Alec, do you want to stay the night?”
I giggled, “Yeah.”
He grinned at me, “OK, take off your clothes and get in bed.” He pointed at the bed while using a fake stern voice.
I giggled again, then did my best military recruit impression, “Yes, sir!”
I yanked my sweater off, leaving my shirt on, then dropped my black slacks and climbed into his bed in just my underwear. I slowly crawled on my knees to the head of the bed, thinking about animals and how they do this all day, every day. Then I flopped down onto my back and spread out my arms and legs like I was making a snow angel as I stared up at all the little bumps on the ceiling, wondering how many bumps were up there; how did they make it bumpy like that?
I felt Jessie’s weight on the bed, and I lifted my head; he was naked. Not even his underwear; his dick was hard and looking huge, bigger than I remember it being. My heart started racing at the sight of him getting between my spread legs, a devilish grin on his face. He scooted up so my legs draped over his thighs, and his hard dick was rubbing on mine through my underwear.
He leaned over me, holding himself up on his hands, and I got a good look at his face. It was blurry at first, but there it was: his pale white skin, cherry-red pencil-thin lips, and dark eyes. His eyes were huge, though, like huge dark saucers right in the middle.
“Are you ok?” I asked, trying to look concerned, but my horniness at this moment wouldn’t let me stop smiling.
He grinned, “I’m fucking horny; my cousin and I took some pills about a half hour ago, and…fuck, it made me so horny,” he nearly shouted, throwing his head back as he said it, then looked back down at me.
“You want to jerk off again?” My heart skipped a beat as I asked the question with too much excitement in my voice.
He grabbed my hard dick through my briefs, holy shit; it felt even better than I remembered.
“You want to try something new?” His eyes traveled from his hand, squeezing my junk up to my eyes.
“Um, like what?” I tried to swallow, but my mouth was bone dry.
“Something I learned in college,” his smile got even bigger, which made me smile.
“Uh…ok, what, what is it?” I wasn’t sure if I even wanted to know, but he kept squeezing my dick, and I had never needed to get off so badly in my life. I wanted to scream “anything” just to drain my nuts, but I was in such a trance…I could barely form the words I had already come out with.
“Have you ever fingered yourself?” He kept rubbing my package and started slowly rocking his hips back and forth so his bigger dick slid over my pouch, teasing my cock trapped in the white cotton.
“What do you mean?” I asked. “I don’t think so,” I chuckled.
His head cocked lazily to one side, “Have you ever played with your ass hole?” The words pulled a smile out of him.
They also pulled a frown out of me, “Um, no, that’s nasty,” I told him.
He chuckled, “When was the last time you showered?”
I had to think about it. The room was spinning, and it was hard to remember five minutes ago. “Umm, oh, right before I came over here,” I chuckled.
“So you’re probably pretty clean back there; trust me, this is…fucking amazing,” his eyes rolled back into his head as he squeezed my cock again, gently rocking his hips against my ass as he did.
“Mmm, ok, I guess,” I said, anything to get off at this point.
He quickly hooked his fingers in the waistband of my underwear and yanked them down, my ass instinctively lifting up so he could pull them all the way off but left them dangling on my right ankle. My cock was on full display, his cock resting next to mine; the heat off his cock was intense.
He leaned forward, pulling at my white undershirt, and I again instinctively sat up off the bed so he could take it off. My legs were forced to wrap around his waist as I did, which felt oddly comfortable. As soon as he took it off, I relaxed right back into the mattress.
I licked my lips and did my best to focus on him, hoping to remember every little detail for future masturbation sessions when he’s gone.
He leaned over to the nightstand and pulled out a bottle of baby oil that was half empty and covered in its own contents.
“What’s that for?” I asked.
“It’s a lubricant,” he subtly shook his head, “trust me, it makes it better for jerking off and fingering yourself; I use it all the time,” he shrugged, opening the cap.
I just nodded in agreement, like I knew what he was talking about. He liberally poured the liquid into his hand, and it made a bit of a mess, dripping out onto my balls; he quickly moved his hand down between us and started rubbing the oil on my ass, then a finger suddenly rubbed my brown eye, and it sent an electric shock into my body.
“Oh shit,” I chuckled.
He kept rubbing, “felt good, right?”
I nodded, confused but excited for more, “Yeah?”
“It gets so much better,” he grinned, adding more lube to his hand, “oops,” he chuckled as it started dripping out of his hand, then he quickly smeared it on his dick, “Good thing I use it to jerk off,” he shook his head, smiling and stroking his dick before returning his oily hand to my ass crack.
“Mmm,” I felt his thumb deliberately rubbing square on my hole like he was trying to strike a Bic lighter; only my ass hole was the spark wheel, and man, that felt amazing. I couldn’t help but squirm under the attention, my body and brain didn’t know how to react to this, but my dick was dripping precum and standing so hard at attention I desperately wanted him to jerk me off. “Can I try the lube on me?”
He smiled, then dripped several drops of the oil on my dick and started stroking my cock gently.
“Oh…fuck,” I couldn’t help but rock my hips up into his fist, it felt so good.
“You like it?” He asked, leaning forward, putting his slightly bigger dick against mine, stroking both of our cocks.
“Oh, yeah, oh wow,” I squirmed, trying not to cum too soon.
He chuckled, then switched hands to his left hand so his right could drop back down and play with my ass again, which almost made me pop off.
“Holy…oh wow, Jessie, ungh,” I thought I might pass out from the pleasure, and then I felt him switch to his middle finger as he added a little more pressure, still rubbing in the tiniest wiggling motion. Suddenly, he curled his finger harder, and the tip popped into my ring up to the first knuckle. “Oh ah…ungh, that’s, oh man, that’s weird,” I groaned, squirming on the mattress. Feeling him inside me was…not right, but also kinda did feel right. I didn’t know what to do or say, so I just let him keep going. I knew he would make me cum soon; I just needed to ride this part out.
He kept jerking my dick with one hand and slowly pushing his finger deeper into my ass with every stroke. So slowly that I might not have even noticed had I not been so laser-focused on the activity down there and worried he was going to hit something inside my ass that neither of us wanted him to touch. “Umm, mmm,” I tried to form the right words to not make this end but also to warn him, “Don’t you think, maybe, you shouldn’t go so far in? Like, um, mmmm, you might, it might get gross,” I warned through moans as he pressed on something inside me that made me feel like I was either going to piss or cum all over…possibly both. “Ungh mmm…”
He chuckled, “I thought so too, but don’t worry, I’d have to get really deep for that to be a problem.”
I clenched the sheets in my fists and nodded, accepting this information as gospel: “Mmm… okay, okay.” I didn’t want this to stop.
“You like it?” He was non-stop, sliding his finger in and out.
“Yeah, mmm,” I nodded frantically, my body still squirming under his attention.
He chuckled again, “Good, let me add a finger,” he said.
Before I could even process the idea, he slipped a second finger into me, stretching my hole more than it was designed to stretch, “Ahhh, fuck,” I hissed and sat up on my elbows.
He grinned, “It’s ok, give it a second, trust me,” he continued stroking my dick, which almost lost all stiffness when he pushed in that second finger, but it was coming back just as quickly, and he was right…two fingers was, kinda, sorta, feeling…”Mmm,” really good. I closed my eyes and tried to enjoy the sensation more. I tried to flex my ass muscles around his fingers while his other hand jerked me off, hoping I would cum, but as I got close, he pulled his fingers out, and it pushed my orgasm back, frustrating me to no end. I had been waiting for this orgasm for months, hoping it would be even better than the last time.
I opened my eyes to see him popping open the baby oil again, dripping a generous amount onto his hand, and then he chuckled again. I thought he was going to use it to slide his fingers back into me, but he wiped the majority on his dick, stroking himself as it made a squishy sound, then he rubbed the extra onto my ass, and I let out a little moan. I spread my legs to let his fingers slip back into me, but instead, he grabbed my hips and slid me even closer to him, then pushed his dick down and started jerking himself off between my ass cheeks.
It felt kinda good. Every time his fist reached the end of his dick, it was bumping into my ass. The constant fapping was feeling really good on my ass, not as good as his fingers inside me, but still good. I started stroking my own dick, needing to cum I couldn’t wait for him to finish me off.
He shifted his weight, and his warm dick was sliding up and down my crack with more pressure, brushing over my hole. Unlike his fingers, which were a bit rough and boney, his dick was thick, soft, and spongy, a much better feeling. I started stroking faster with this new soft pleasure, “Ow! Ah,” I grunted, the sudden, most painful thing I have ever felt in my life as he rocked his hips up, and the head of his cock was pushed into my tight little hole.
I sat up on my elbows and looked up at him. His naked body was between my legs exactly like last time, but instead of his cock rubbing along mine, it was pushing into my hole. The sting was so intense I couldn’t breathe. My mouth formed a scream, but no sound came out. I looked into his eyes; they were even bigger and darker than before, and he just smiled down at me. “I need some ass,” he chuckled.
“Ow…shit, not my ass, man,” I groaned, falling back onto the mattress as another inch pushed into me.
His face scrunched up, “You’re going to blue ball me?”
“I…what? Ungh…No,” I didn’t know how to respond to that, and the pressure and fire burning in my anal ring was brutal.
“Then let me fuck you,” his voice was so gruff like he was possessed or something. He shoved another inch into me; more of his dick was inside me than not at this point. He grunted as he hit a point where he couldn’t push in anymore.
“Fuck,” I grunted, “I can’t…it’s too much,” I groaned. I felt like I was being torn in half.
Jessie leaned over me, his saucer-sized eyes searching mine, “I’m already in; you’re already getting fucked,” he said in a hushed tone as he gyrated his hips, biting his lower lip to hold back the sounds of his enjoyment.
I was too high to fight it, and the pain was succumbing to a hint of pleasure. I didn’t want to give Jessie blue balls; what kind of friend would I be if I did that?
“Ok, just…ah, take it easy, man,” I hissed, wincing as he rocked his hips into me again. Does he do this with his other friends?
He grinned and nodded, reaching down to grab my legs and put them on his shoulders, damn near folding me in half, lifting my ass up almost a foot off the bed. He pulled his dick slightly out and then shoved it back into me, his hips hitting my ass cheeks with a fap sound. I let out a sound that was halfway between a moan and a squeal.
“That’s it, that’s it,” he grunted, fucking me harder and faster.
I gripped the sheets below me with my fists; my eyes shut so I didn’t have to watch as he penetrated me over and over again. I was trying my hardest not to like it, but the longer it went on, the better it felt. I realized at some point I was rocking my hips in sync with his thrusting, his dick was hitting something inside me that felt so good I had to hold back a moan so he didn’t think I was enjoying this as more than a friend or something, but my toes were curling behind his head, my underwear still dangling on my ankle behind his neck, my dick was hard as a rock, I think he knew I was enjoying it at this point.
He had only been fucking me for a minute, but I didn’t want it to go on too long, “Fuck, are you close?” I asked through clenched teeth in a breathy voice.
“I’m real close; you’re doing so good,” he whispered. His breath smelled like alcohol, and his eyes were even wider than when we started. His face was still so pretty, and his body was flexing every muscle he had to push himself inside me.
“Mmm, ok,” I accidentally moaned.
He picked up on it and started fucking into that spot inside me over and over again.
“Ungh, fuck,” I groaned, holding my hand on his hip, trying to stop him from making me like it. I didn’t want to be his bitch, but fuck, this felt so good.
“Yeah, take it, Al, take my dick,” he grunted, thrusting harder and harder.
“Umn…mmm, are you close?” I begged.
“I’m close, real close,” He leaned all his weight on my legs, his cock sinking even deeper inside me as he fucked me.
“Ok, ungh, hurry,” I said; I felt like I was going to piss myself, and his thrusting was pushing on something that was going to make me do it.
“Ok,” he said, grabbing my shoulders and pinning my knees to my chest, pat pat pat, his hips slammed into my ass, sending pleasure into my hole with every thrust.
“Mmmm,” I moaned, desperate and delirious from the pleasure. I had no idea guys could give each other this kind of pleasure, but holy fuck, it was amazing! I clenched my fists tighter to the sheets, trying my hardest not to moan but failing.
“Oh yeah, oh yeah, ungh,” he grunted and pulled me tight to him, so tight I could barely breathe. With the added pressure and his dick burying deep inside me, I felt it swelling and twitching; the warmth inside me felt so good and silky. Suddenly getting fucked felt insanely amazing, but he stopped fucking me, slowly to a complete halt.
“Mmmm, fuck,” I groaned with what little breath I had in me. He held me tighter, rocked his hips out ever so slightly, and then back in again, grunting in my ear as his breath melted on my neck.
The warmth inside me was more than his cock; I felt so full and wet I had a bit of a panic, “Shit, did you piss in me?”
He chuckled, “No, I blew my load,” he continued laughing and slowly pushed himself up.
“What?” I nearly yelled. “You…you shot your cum in me?”
“Yeah, what did you think would happen?” He smiled at me, slowly pulling his deflating cock out of my hole.
I reached down, feeling the wetness, smelling it on my hand; it was definitely cum. “Fuck man, that’s so gross,” I scowled at him.
“Nah, it’s fucking hot; you took it like a champ, too,” he grinned.
I didn’t know how to react; I was grossed out by the idea of his load inside me, but I had a sense of pride for having gotten him off and not giving him blue balls, a huge plus that he seemed to respect me for it. He reached out and started slowly stroking my dick. Then he dropped down, licking it with his long tongue like it was a melting ice cream cone. The precum leaking down was lapped up quickly, and he took my entire dick in his mouth.
“Wait…mmm, yeah,” I was going to stop him, but that felt amazing. Another thing I never thought of doing with another guy. He was either really skilled, or I was really horny, but he only bobbed up and down a few times, and I felt my balls tighten. Then he slipped two fingers into my hole, and it pushed me right over the edge, and I filled his mouth with my cum. He continued to suck me another few seconds after I shot my load until my dick became really sensitive, I had to push him off me. “Fuck, that was…fuck,” I huffed out of breath.
Jessie slowly pulled his fingers from my hole, then wiped the wetness from the corners of his mouth like it was ice cream and licked his fingers, both of us knowing it was my cum.
I scrunched up my face, “Ew, did you swallow my stuff?”
He chuckled, “Of course, now we’re cum brothers,” he grinned and then stuck out his tongue to show that he had swallowed it all.
“Ugh…do not tell anyone that,” I groaned but couldn’t hold back a smile.
He flopped down on the bed next to me, “fuck, I’m spent.”
I stretched out, still catching my breath, looking down my naked body, then over at his naked hairy ass, wondering if he would let me do him too? When he started snoring I realized that was a question for another night.
