ADAM:
When I was little, I spent more time in my sister Amy's room than in my own. Amy had a huge, expensive, pink Barbie Dreamhouse and it was my favorite toy in the whole world. I cried and begged for my parents to buy me one, but it was met with the expected "boys don't play with dolls." So my earliest memories all take place in Amy's room, playing with her toys behind my parents' backs.
Thankfully, my sister was a good sport about it and she let me play with her stuff as much as I wanted, oftentimes playing together with me. She was four years older and my best friend, even though I knew I wasn't hers. My sister was always very popular and had a gaggle of girlfriends who took precedence over me in the friendship hierarchy. As time went by, they neglected Amy's Barbies more and more, leaving me to play alone while they talked about one thing and one thing only: boys.
At first I didn't get what all the hoopla about boys was, until I started going to school and developing crushes of my own. Of course, the crushes Amy and I had on boys were very different. I knew I had to keep mine secret, and that's what I did. I noticed most boys were into sports – something I never had an interest in – so to get closer to them I signed up to play soccer, which thrilled my parents. This led me to my favorite as well as most dreaded place of all: the boys' locker room. Every time I was there, I looked at the other boys with an interest they didn't seem to have for each other. It's where I had my very first boner; and even though I didn't know what it was at the time, I knew that I had to hide it and get away as fast as possible. This novel thing in my underwear was a traitor; a messenger here to announce to everyone that I was a freak and a weirdo.
I was 9 years old when my sister got her first boyfriend, a boy named Jonah. Jonah played soccer as well, so he and I would kick a ball in the backyard whenever he came over to our house. I was a subpar player but Jonah actually taught me a few good tricks, which impressed my coach later on. My parents' house had a pool, and we also took advantage of that sometimes when Jonah was over. If he ever needed a pair of swim shorts he would borrow one of mine (even though they were kinda snug on him). I had to be very careful during our swim sessions, because that was usually when "the traitor" made his return. If I popped a boner in the pool, I had to wait carefully until no one was looking so I could sprint to my room or the bathroom. I'd realized that the only way to get rid of the traitor was to do what I later learned was called "jerking off." As I had a wank over the toilet daily, the first subject of my fantasies was my sister's boyfriend Jonah.
Amy and Jonah's love affair was not one that would stand the test of time and it ended as they graduated middle school. Amy's boyfriends in high school were even hotter. To me, they looked like grown, adult men; some of them were even taller than our dad! Not only was I younger but I was also short for my age, which made me look up to them in more ways than one. I would try to go into Amy's room whenever they were there, but I no longer had an open invitation to my sister's room. She would shut the door in my face and lock it, entertaining her boyfriend du jour in privacy. Sometimes I would kneel there and press my ear against the door, listening to the sounds of kissing. I pictured myself making out with whatever high school hunk was in my sister's room, envying her good luck in life.
One weekend when I was 13, my parents went away for a couple of days, leaving Amy in charge of looking after me and taking care of the house. Of course, the first thing my sister decided to do was throw a party.
"If you promise not to tell Mom and Dad, I'll let you hang out with us and give you fifty bucks," my sister said to me. As far as I was concerned she could keep the money; all I wanted was to hang out with her boyfriend and her other male friends, many of whom looked like fucking models. Puberty was less kind to me. I was scrawny, short, had acne; all contributing to my social awkwardness and crippling anxiety. Still, I was determined that for this party I would get my shit together and try to be cool for the first time in my life.
Turns out: easier said than done. As Amy's guests arrived, none of them wanted to hang out with her dopey little brother. They all made a beeline straight for the liquor and then huddled together in groups, excluding me. I forced myself to have a beer, partly because I thought it would make me look cooler but also because I'd heard it helped people relax. I hated the taste of it, but after a few more swigs it started to become more tolerable. Just as I finished my first bottle and opened a second one, there was another knock on the door and I went to answer. There, I was surprised to see a group of boys that also included none other but Jonah.
I hadn't seen Jonah since he and my sister broke up and I always assumed they hated each other or something, but apparently they were friendly enough for him to receive an invitation to the party. I stood to the side and watched as he said hi to my sister and chatted with the rest of his friends. Then unexpectedly, Jonah came up to talk to me.
"Hey, Adam. It's been a while," he said with a friendly smile as he clinked his beer bottle against mine.
"Yes. I– I didn't expect to see you here," I stuttered.
"How come?" he asked.
"Well– Well I didn't know that you and Amy were still friends."
"Oh yeah, we still talk. I'm actually friends with her boyfriend as well, we play football together," said Jonah, who by now had progressed from soccer to football.
"Cool. And are you seeing someone?" I blurted, feeling stupid as soon as the words were out my mouth.
"Nah, we just broke up," Jonah replied and took a swig of beer. "My ex might be here, actually," he added, looking around the party.
"What does she look like?" I asked.
"He's got longish brown hair with some green strands in it. And he always wears these large geeky glasses even though he can see perfectly fine. So if you spot someone like that let me know so I can hide," Jonah said casually and then took another swig of his drink.
Meanwhile, my head was whirling. "HE"?!! The last person Jonah dated was a guy?! I was always interested in him, but now that interest was multiplied by a million. After a brief chat, Jonah left to rejoin his friends, and I kept my eyes on him as much as I could. I didn't wanna look like a crazy stalker, but I just couldn't help it. Then, when I spotted Jonah going upstairs to use the bathroom since the downstairs one was occupied, I quickly followed him up the stairs.
I waited in the hall for a couple of minutes for Jonah to come back out of the bathroom. Then when he did, I pretended to be passing by on my way to my room.
"Hey, what's up?" Jonah smiled at me again.
"Oh, I'm just done with the party. I was gonna go hang out in my room. Wanna come?"
Once again, the words were out my mouth before I knew what I was saying. I could feel a buzz in my head and I was starting to realize it was probably the beer. Thankfully, Jonah's reaction to my invitation was positive.
"Sure," he nodded. "We can hang out for a while."
I took Jonah to my room, quietly berating myself for still having some toys on the shelves even though I was now a teenager. I closed the door behind us, drowning out some of the music blasting from the living room.
"Last time I was in here I think I was putting on a pair of your swimming shorts," Jonah laughed, looking around.
"Well I still have some, if you wanna put them on," I said, taken aback by my own joke.
"Nah, I'm good for now," Jonah winked at me.
"So, umm… Did you see your ex-boyfriend downstairs?" I asked, eager to talk about Jonah's love life some more.
"No, I don't think he's here. He doesn't hang out with Amy and her friends."
"How long were you guys together? You and this guy, I mean?" I asked, sitting on the bed as Jonah sat on my desk, taking a swig of the beer he'd brought along.
"A few months, nothing too serious," he replied coolly.
"So, uh… Are you gay now?" I finally got myself to ask.
"I'm bi," he answered, then smiled.
"I think I'm… I think I'm gay," I stuttered nervously, uttering those words for the first time in my life.
"Well good for you!" Jonah said, sounding congratulatory. "I had a feeling you might be."
"Really?!" I asked, genuinely shocked.
"Yeah. Honestly… it's kinda obvious," Jonah said to me. "But that's not a bad thing! And it'll make meeting other guys easier."
"Yeah, right," I rolled my eyes. "As if anyone would ever date me."
"C'mon Adam, why would you say that?" Jonah looked at me compassionately.
"I've never had a boyfriend!" I said loudly.
"So what? Dude, you're like super young."
"My sister had a boyfriend when she was 13. She was with you!"
"Who cares about your sister? You do what's right for you."
"I haven't even had a first kiss," I added, looking away and hoping that I wouldn't start crying.
Next moment, Jonah got up off my desk, walked the few feet to my bed, squatted in front of me, and planted a peck on my lips.
"There. Your first kiss," he whispered while holding my chin in his hand. "And when the time is right you'll find a guy to give you many more. Now, how about you brush your teeth and go to bed? No more beer for you."
Jonah smiled, mussed my hair, and walked out of my room… and out of my life. The following year he started college on the East Coast, moving out of our Texan town and leaving me to jerk off to the fantasy of him once again.
—
As the years went by, my sister's relationships started getting more substantial. In college, she started dating Earl Harland. The Harlands were a well-respected family and with their eldest son Thad already married off, Earl was probably the area's most sought-after remaining bachelor.
I was 19 now, going to a nearby college and still living at home. Even though I was an adult, I still felt like a child compared to men like Earl. At 6'2", he towered over me. He was ten years older than me and he seemed to have his shit together: a good job, his own house, a pretty girlfriend he would probably marry some day. In the meanwhile, I was as much of a fuck-up as always.
I'd still never been in a serious relationship with a guy, but that definitely didn't mean I was still a virgin. Quite the contrary. Since starting college, I'd become somewhat of a slut. I'd hooked up with several of my classmates, one of my professors, and plenty of horny men around town. I'd joined the college gym, both because I was trying to get in shape as well as the fact it was an excellent spot to go cruising for dick. I was the bottom party in all of my rendezvous, often going back home with two or three loads inside me from the day's encounters.
One day, while running on the treadmill and staring at a particularly hot guy at the gym, I flew right off the machine like an idiot, making a spectacle of myself. As if that wasn't bad enough I also injured my leg, making it really hard to walk. When my sister heard about it, she told me to go see her boyfriend. Earl was a physiotherapist, and an incredibly successful one at that. Amy told me to go see him at his office at 6 that evening; a prospect that filled me with both excitement and anxiety. This would be my first time being alone with sexy-as-fuck Earl.
I skipped class that afternoon and limped to my room, where I shaved and clipped my nails, as if my sister's boyfriend would be judging them. I was just about to get dressed in a nice pair of jeans when I got an email from his office, confirming my appointment and asking me to wear comfortable clothes. So instead of the jeans I went for a pair of basketball shorts, which unfortunately made me look frumpy rather than sexy. Then, in an effort to sex it up, I decided to get rid of my underwear and go commando.
When I got to Earl's office at 6 PM, his receptionist was on her way out, leaving Earl and me alone. Fuck, he was so handsome! I melted as Earl patted my back and smiled at me, leading me into a room with a massage table. He was wearing a button-up and slacks, and interestingly enough he had his shoes off, walking around in his socks. He asked me to lie on my back on the massage table and explain what the problem was.
"I fell off the treadmill today and walking is really painful. It's my right leg, right here," I said, touching the back of my knee and moving up.
"Let's see," said Earl, and he got in position. He lifted my leg and touched several spots, constantly checking in to see if it hurts. After a while, he propped my leg up on his left shoulder, venturing higher and higher up my thigh with his hands. That's when I realized I was in trouble. Maybe going commando wasn't such a good idea after all! Being touched by this incredibly attractive man made my blood rush straight to my dick. In less than a minute, I was pitching a tent so big it was impossible to overlook; it was basically poking Earl in the eye. To make matters worse, from the position we were in he could also see straight up the leg of my basketball shorts, probably getting a view of my balls and rock-hard dick.
"I'm– I'm sorry," I apologized awkwardly, figuring there was no point in ignoring the situation.
"No worries, happens all the time," Earl smiled and said professionally.
"Really?!" I asked. I knew Earl had a ton of celebrity clients, and the thought of these famous basketball and football players getting hard on his massage table only made me more erect.
"Well, not really. But it happens occasionally," he admitted with a chuckle. Interestingly, he never let go of my leg. The skin-on-skin contact continued as his fingers slid higher up my thigh, going inside the leg of my shorts. Then Earl asked,
"Can you please roll your shorts up? I would ask you to take them off but from what I can tell you're freeballing it today," he chuckled again.
"Yeah, sorry. Laundry day," I lied. I rolled my shorts up and my sister's boyfriend proceeded with his examination and the little massage he was giving me. The fact that he was a complete pro about this rather than a perv only made me hornier! My cock started throbbing, wagging back and forth like an excited puppy's tail, begging for attention. I specifically noticed Earl looking right at it several times, which led me to start leaking precum, leaving a noticeable stain on the green fabric of my shorts. I was equal parts turned on and horrified! Thankfully, a few minutes later Earl said,
"Turn around please."
Lying on my stomach, at least I could hide my embarrassing erection for a while. Early continued to touch my thigh, going further and further up until his fingertips were grazing my glute. My ass was obviously a very erogenous zone for me, so I bit my lip and closed my eyes, drowning in the pervy pleasure I was getting from all of this, as inappropriate as it was. With my boner rubbing against the massage table, I couldn't help but start thrusting my hips ever so slightly. The sensation was surreal! Earl's hand continued going up, basically squeezing my asscheek. I knew I was wrong for doing this, I knew I was getting myself into trouble. My cock throbbed, rubbing against the table, when suddenly… I began to blow my load!
I bit into my lip even harder, stopping myself from moaning out loud as I jizzed inside my shorts. Earl was still massaging my glute, probably oblivious to the effect it was having on me and the fact that I was cumming in that very moment. I continued to shoot my nut, feeling it seeping through my shorts and onto the massage table.
"Good news is it's just a strained muscle," I heard Earl say just as I was shooting my last wad of cum. He laid my leg down on the table and said, "I'll give you some stretches to do and you oughta feel better in a week or so."
I remained lying on the table, my cock still throbbing in post-orgasmic pleasure.
"You can get up now," my sister's boyfriend told me, standing next to the massage table and offering me his hand.
"Umm…" I looked up at him. "This is really embarrassing, but… Do you have any tissues or something I can use? Because I've…"
"You've what?" Earl asked, genuinely puzzled.
I knew that no matter what I do I wouldn't be able to hide this. There was no getting up without showing the huge cum stain on my crotch. So I finally lifted myself off the table, accepting Earl's hand as he helped me get up. Then, he looked down and realized what the problem was.
"Oh!" he said. He looked shocked, but he quickly shook his head and tried to appear normal. "Yeah, man, I got some tissues here."
He walked to his desk and handed me a box of Kleenex. The first thing I did was use a few to wipe my cum off Earl's massage table.
"I am sooooo sorry about this," I said, feeling mortified.
"That's okay. No worries," he assured me. Although the situation was awkward as fuck, he was actually doing a really good job at making me feel comfortable.
After cleaning up the massage table, I tried using tissues to get the pearly-white stain off my shorts. It was to no avail, of course, since the damage was already done.
"If you want, I have some pants you can borrow. I keep a few pairs at the office," Earl offered. "Sometimes I need to change in the middle of the day if I get sweaty."
"Actually… You would be a lifesaver if you did that," I said, looking at Earl and getting all red in the face.
"No problem," he smiled at me and walked to the closet. He came back and handed me a pair of slacks as well as nice, gray boxer briefs. "I figured you could use those as well."
"Thank you," I said, at a loss of words at his kindness.
"I'll let you change," Earl said and left me alone in his office. I took my shorts off and wiped the cum off my dick. It had started to go soft after cumming, but now it was growing again, excited at the prospect of getting into a pair of Earl's underwear.
—
Two days later, I washed Earl's pants and underwear, and I drove to his house to drop them off. It was around 9 in the evening and I knew my sister wouldn't be around since she was out of town for a few days. Otherwise, I would have a hard time explaining why I ever had to borrow her boyfriend's pants and underwear, and I hoped that Earl had decided to keep the secret from her as well.
Even though I was dropping over unannounced, Earl greeted me with a welcoming smile. He was wearing a white T-shirt and plaid boxers, and I could hear the TV in the background. He was obviously winding down for the evening and he invited me to join him for a couple of beers. I was happy that even after the embarrassing incident at his office, Earl was still completely normal with me.
We had a round of beers, and then a second one. Eventually, of course, we wound up talking about my sister.
"So, if I may ask… Do you think you guys are gonna get married soon?" I said.
"To be honest… I don't know," Earl sighed. He could've simply laughed it off and said something like "haha, we'll see," but the fact he was willing to open up to me really meant a lot.
"We've been together for quite some time now," he continued, "and I know we look perfect to the rest of the world, but like in every relationship there's ups and downs. So we'll see."
We talked about Amy and all of her strengths and weaknesses for a while, until we finally moved on to talking about my love life. I'd had three or four beers by then so my tongue was pretty loose, and I let Earl know that even though I wasn't dating anyone, I was slutting it around campus and getting a lot of dick. Earl just laughed and assured me he did the same when he was in college, getting into as many girls' pants as he could.
"It's your time to go wild," he said and winked at me.
I made Earl tell me some of his crazier stories from back in his college days. Whether it was the alcohol or the fact that he'd already seen me blow a load, Earl was very open with me. We were talking about sex in an uninhibited manner unlike ever before. He told me about fucking some girls in public around campus or fingering them during class. Hearing these stories from the handsome man who might someday be my brother-in-law made me pop a boner in my pants once again. This time, thankfully, I was wearing jeans so it wasn't that obvious.
Earl, on the other hand, was only donning some boxers. Talking about his sexcapades was clearly having an effect on him as well, as he soon began to fill up his pouch more and more. Even soft, it was obvious to me that Earl had a nice-sized dick, but minutes later that thing began to pop out of the fly, which nearly gave me a heart attack.
"Sorry about that," Earl chuckled and tried hiding his rising dick. It was his turn to apologize for his horniness this time.
"Hey, it's nothing I haven't done in front of you already," I reminded him.
"Yeah. I know it's weird to say this to Amy's brother, but one of the best things about her is the sex. So on nights like this when she's gone, I'm not used to being on my own," Earl said, still tugging on his dick as he spoke. He was casually stroking himself through his boxers, and by the looks of it he was almost completely hard by now.
"Don't worry, I know all about my sister's… talents," I admitted. "When she lived at home, I used to eavesdrop on her and her boyfriends in her room all the time."
"Oh really?" Earl smiled, never letting go of his dick.
"Yes. Let's just say it motivated me to learn a few tricks as well," I smiled, placing my hand on my bulge and beginning to rub myself through my jeans as well.
"I'm sure you get plenty of tricks," Earl chuckled. We were both looking at each other's eyes now and shamelessly stimulating our pricks,
"A fair amount. And they have no complaints," I said seductively.
"So how come you're not dating one of them?"
"Ah, it hasn't worked out. Plus, a good amount of the older guys I hook up with are married. They insist they're straight. They just wanna have a guy's ass for a change."
"Aha," Earl let out a guttural sound that was halfway between a grunt and a moan.
"So have you?" I asked.
"Have I what?" said Earl.
"Tried a guy's ass?"
"Can't say that I have," he said and then he smirked.
Feeling tipsy and horny for Earl, I got up and pulled down the back of my jeans, exposing my ass to him.
"Wanna try this?" I asked, shaking it in his face. I wasn't the handsomest or most muscular guy in the world, but I had an amazing ass that I was quite proud of. Apparently, it was tempting to Earl as well, I could tell. I could see it in his eyes as he looked at me and stroked his dick even more vehemently, taking it out through the fly of his boxers and pumping his fist up and down his shaft.
"I dunno. Your sister can't find out," he said to me.
"She won't. You kept my secret about cumming at your office. I'll keep this secret," I promised.
"C'mere," Earl beckoned me toward him. I took a few steps back until my ass was in his face. Then, straight-man Earl surprised me by burying his face between my cheeks, eating my ass like a seasoned pro. The sensation of his tongue on my ass lips was incredible! I pushed out, letting Earl have more of my ass as he kissed it, lips-to-lips.
"When's the last time you've been fucked?" he asked.
"Umm, about a week? Which is a long time for me," I replied.
"Well let's end that streak," said Earl and pushed me onto the couch. I was on my knees, with my ass in the ear, as Earl stood up behind me and positioned his prick between my cheeks.
I was used to sucking men's dicks before they went up my ass, if nothing else then to help them get hard, but Earl needed no assistance. He slapped his rod against my cheeks to let me know just how hard he was. His cock was so big and heavy that the noise it made reverberated around the room
"Ahh, fucking go inside me," I begged, taking my own erection out of my pants and stroking myself as I felt Earl's cock pressing against my ass lips. Little by little, my sister's boyfriend pushed in until his entire circumcised cockhead was inside of me.
"AH, YES!" I moaned loudly while Earl's shaft split my asshole in two. After having a crush on every single one of my sister's boyfriends, I finally had one of their cocks up inside of me. Earl placed his hands on my ass and squeezed and kneaded my cheeks as I moaned and cried out.
After about ten minutes fucking this way, Earl flipped me over so I was on my back. Now that we were face-to-face, we made eye contact and I was surprised as Earl leaned down and planted a passionate kiss on my lips. Most of the "straight" men I got fucked by avoided kissing at any cost. Earl's dominant tongue dove into my mouth without asking for permission, making me open up both holes for him. I let go of my cock, since I didn't need to jerk off anymore. The pleasure I was feeling as Earl's cock tapped my prostate was enough to bring me close to orgasm all on its own. And I wasn't the only one that was on the edge.
"I'm gonna cum soon," Earl panted in my face. "I need to pull out."
"No! Shoot inside me," I insisted.
"Fuck man, you serious?"
"What're you afraid of, that you gon get me pregnant? Fucking cum inside me!" I ordered. A few moments later, I got my wish.
"Ahhh. AHHHH, FUCK!!! Ahhh, fuuuuuuckkkk!!" Earl shouted and blew his babies inside my ass. As I felt his jizz flooding my hole, I shot my own load all over my torso without even touching myself. Some of it even shot as far up as my face, coating my lips and cheeks in warm cum.
"Fuck. Fuck. Fuck," Earl and I continued panting in symphony. Finally, a minute or two later, we were done cumming. To my further surprise, Earl leaned forward once again and planted another kiss on my lips, ignoring the cum that was on there.
"Remember, this is our secret," he whispered and went back to kissing me while still thrusting his cock back and forth inside my asshole, churning the cumload he'd just deposited there.
—
Although we both kept our secret hidden, Earl and Amy broke up two weeks later. When I got a chance to talk to Earl he said that he couldn't deal with the guilt of having fucked Amy's brother, but there were also other reasons that led to their breakup. I insinuated that he was free to call me up any time if he needed to a drop a load, but we never fucked again.
Instead, something even better happened: my sister's first boyfriend Jonah finished grad school and moved back to town. He and I reconnected, and interestingly enough he became my first boyfriend as well! A few months in and things are going strong between us. Maybe if I play this right he'll also be my last boyfriend, and he'll become much more than that someday.
​
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