This is a true story of my first time with a guy when I was 20 in college while working as a delivery boy. I was 5'11 about 175 lbs very lean muscular, dirty blonde hair and clean cut. barely got any peachfuzz, I was a typical "pretty boy". Some of the quotes are more what I remember the sentiment being, not word for word.
I was in my junior year of college, unlike most of my friends I decided to commute to a local college to save money and while attending worked as a delivery driver for a local restaurant. For the first 2 years of college I had a girlfriend that went to a different college about an hour away and most weekends I spent with her staying in her dorm but we had broken up as she was leaving to go back to school. I wasn't really heartbroken or anything like that and mostly fine with it but I was going to miss having sex regularly especially not living at a college and being from a small town with not many options, also apps like tinder hadn't really come around yet.
I loaded my schedule to have classes only on 2 days which previously meant I could see my girlfriend more but now just meant I had way too much free time. Like most horny 20 year olds I was watching a lot of porn which led to even ready erotic stories which led me to discovering all different levels and types of sex I didn't really know know much about. I remember reading a story about a couple who were swingers which started off really hot but eventually pivoted away I didnt see coming, during a threesome with another guy the wife pushed the man to try sucking his cock. I remember being shocked but also shocked that I was still hard reading it, I tried to tell myself it was just the lead up to that part had me so turned on or I was just too horny but either way I kept reading. After that I found myself reading more stories about couples like that until I eventually found myself reading stories just about men having sex and typically a guy having sex with a man for the first time.
I didnt think about it much at the time but when I was ready stories about men having sex it was typically a younger guy like myself and an older man, either being seduced or seeking it out. I hadnt thought I was attracted to older men but something about those stories really stuck out to me and turned me on more than the rest. Looking back it sound naive or funny that I didn't think I had a "type" given what turned me on the most, I still didnt ever feel sexually attracted to guys necessarily as I wouldn't see any guys and think they are hot or would want to do anything with them. The more I read these stories the more I'd wonder if I would ever actually do anything with a guy, when I started reading the stories it was almost like I thought it was hot for them but as time went by Id read them and start to picture myself in the story, the young seemingly straight guy seduced and being fucked by an older man, a "daddy".
During this time I was working more weekend nights, better tips and since I had no girlfriend to visit and my friends were away at school I had nothing better to do. I worked every Friday night which was the most busy night of the week, I was driving non stop until close and the last delivery was always the same exact guy, Rick, I'd cash out from the restaurant so I could make that delivery and go straight home. The guy was very nice, appeared to be in his 50s if I had to guess but objectively looked great for his age, he was just over 6 foot, short dark hair with a short but thick beard and very built. Even in clothes you could tell he hit the gym regularly and hard and while he wasnt much taller than me he had some serious weight and muscle on me. The first time I noticed was when he had a tshirt on and even in that you could see his traps popping and his forearms were huge and veiny. Since I'd see him literally every Friday at the same exact time we chatted a little bit, not much as I was usually just wanted to get home and play video games but he was nice. While I wasn't thinking about actually having sex with him, or so I thought, when I would read stories occasionally I'd read a description of the "daddy" and he'd fit the bill, he was very much a classic hot daddy. While he was very masculine and manly he did make comments about me that would make me think he was gay, like clearly hitting on me but not so much that it was completely obvious or uncomfortable, also he was a great tipper so I was fine with it. To make it even more obvious he would also put on hand on my shoulder as he thanked me and once even put his hand on my back, he was clearly drinking that night as I could smell it on his breathe.
Over the weeks and the more I'd reach these erotic stories the more I found myself, almost daily, reading stories about younger men with older guys, daddies, as they seemed to turn me on the most. Many of the descriptions of the daddy matched this man and I started to picture myself in the story with him, I couldn't read a story without picturing him, it was too the point that just delivering to him I'd notice myself getting hard and trying my best to hide it as he'd make comments about how cute I am, and how Im the highlight of his week. A couple times I honestly thought I came close to saying something back to him but I couldn't get the words out, a mix of fear and not knowing what to even say, I think at this point he started to notice something was clearly up. As much as I was picturing myself with this man, I was still telling myself I didnt actually want it and that I was just really horny from not having regular sex with my ex, I was actually into the idea of being with a guy and specifically him. But the every day I'd try and focus on straight erotica or porn only to eventually move to stories of young men with a daddy and I'd lay there stroking my cock picturing myself with him.
One January night I was making my regularly end of the delivery night to him and rang the bell. I was standing there for a couple of minutes and rang it again, thinking maybe he just didn't hear but eventually he opened the door wearing nothing but sweatpants. He clearly just got out of the shower as his hair was still wet and I couldn't help but admire his body, he was more muscular than I was expecting. He had a big burly muscular build to him, big pecs shoulders and biceps, a gut that wasn't fat almost protruding with muscle, this man was a powerful bruiting man.
"Im so sorry, i was taking a shower and lost track of time. Come in from the cold while I find my wallet"
I followed him into the house as he led me through the foyer into a big kitchen that blended into the living room, he was scurrying around for his wallet as I stood there just looking around while also admiring his body, his back was so muscular.
"Sorry for this, I'm sure you have other deliveries you need to get to"
"It's ok. this is actually my last one. I just go home from here" I instantly thought that was a mistake, he's going to make a move.
At the time I lied to myself saying I didn't want him, it was just the porn and stories had gone to my way too horny head and I was now just inviting him to make a move. I think even then I knew if he did make a move I would give in.
"Well in that case have a drink while you wait, I know it's here somewhere" and he goes over to the bar cart and pours me a glass of whiskey and tells me to take a seat on the couch.
I remember thinking I shouldn't have whiskey and then drive, even one glass would make my breathe smell but also the bottle looked nice and most of the whiskey I drank was knock-off Jack Daniels so fuck it. I did think it was a weird offer especially to someone like me who was clearly young and looked even younger for my age but I was fine with it. As I was looking around I was realizing how big the house was, it was a bit off from teh street, long driveway and not well lit so it was hard to tell the true size from outside, but inside I could see it was actually huge.
"Left it in my pants pocket, sorry about that" as he walked back into the room, still shirtless, and I stood up.
He had also apparently poured himself a glass he was holding as he handed me the money.
"Thank you for your patience. Since you aren't in a hurry want the tour? Don't have too many guests since I moved in and wouldn't hate someone to share a drink with"
I honestly started to feel bad, thinking he was just being nice and maybe not flirting, he was just lonely so I said yes. He took my jacket off of me and placed it over the chair and started to lead me through the house, starting in the kitchen, going back through the foyer and leading me to his "reading room" the entire time I couldn't help but stare at his muscular back. When we got into the reading room it was lined with bookshelves, big thrown like chairs and a table between them, as he was talking about building it almost showing off I noticed a magazine laying on the table, I'll never forget the name "BEAR" and had a big burly man similar this guy on the cover. I starred at it almost wanting to pick it up before I was snapped out of my gaze
"Lets head upstairs"
My head snaps back as I follow him, hoping he didn't notice what I was starring at as he seemed to be so excited to just talk about his place. We made our way up the stairs going from one room to another, all perfectly decorated and furnished and he had so much to say about each. I couldn't stop thinking about he magazine and him, seeing his body just flaunting in front of me had something inside me stirring that I was trying to fight as much as I could.
"Last stop on the tour" as he stood at the doorway and held his hand out inviting me into the room.
I took a step in and it was clearly the master bedroom, it was big like most of the rooms furnished with what appeared to be very expensive furniture and a big king bed. I stood there for a second and before I could take another step I felt his breathe on the back of my neck followed by his big burly body pressing against my back. I was completely frozen, almost in shock my mind racing thinking "oh my god this is actually happening, I need to go now" but I didnt, I stood there frozen.
"how'd you enjoy the tour?" directly into my ear with a whisper
"uhh... it.. good" I couldnt form a sentence, terrified, horny, I didnt know what I was feeling.
"I saw you looking at that magazine. See something you like?"
"uhh... I dont.. know" I was lying, I knew I was lying
"Your body is telling a different story" as I felt his left arm wrap around my chest and his right hand slowly move to my crotch giving my rock hard cock a light squeeze, I didn't even know I was hard.
"It's ok boy, i saw the way you looked at me. Admiring me, you like daddy's body, dont you boy?"
"I... dont... kind of" my heart was racing as my breathing intensified.
He slowly spun me around now almost face to face with him, my nose just below his, his hands slowly moving from my hips to my ass, I did nothing to even try and stop him.
"Mmmmm you have a great ass, daddy loves a sexy boy like you" I took a deep breathe, almost a whimper
"thank you" was all i could say, I didt even think what I was saying.
"It's thank you daddy for now on boy"
"Thank you... daddy" I couldn't believe I just called this man daddy but saying it outloud turned me on so much
Without warning he grabbed the back of my head and pulled my face into his, he began to make. It was the first time I had ever kissed a man, I had thought it'd feel so weird to kiss another man but something about it felt so different but in a good way. He was so powerful, tender and passionate, his power to overcoming me, almost like I was "the girl" but it was intoxicating. We stayed there for a couple minutes making out, my hands rubbing all over his muscular back as he held my head with his left hand and squeezed my ass with his right. He pulled my head from our kiss holding me by my hair looking me right in the eyes.
"You going to be a good boy for daddy?" I couldn't believe I had a man actually talking like this to me.
"yes daddy" I just remember those words flowing out like I had been dying internally for them to finally come out
"Good boy, now take those clothes off"
I quickly took my shirt off, followed by my pants and underwear, kicking my socks off, standing there completely naked infront of this daddy who still had his pants on just examining me.
"The second i saw you I knew you'd have a sexy body" as he walked up to me caressing my body and my breathing intensified.
"You want to see daddy's cock dont you boy?"
"Yes daddy" I was so eager I needed it.
He slowly pulled his sweat pants down and kicked them off, his legs were like tree trucks and his cock, it was a beautiful cock even soft my mouth started to water.
"You want to suck daddy's cock don't you boy?"
"yes daddy"
"No, I want you to say, tell me what you want"
"I.. I want to suck daddy's cock" as he smirked at me and led me to the bed.
He hoped onto it, sitting up against the pillows as I climbed on, instinctually going right between his legs as i reached and grasped my hand around his hardening cock. I slowly started to stroke it as I starred in awe until I finally started to lower my mouth until finally I had his cock in my mouth, I let out a light moan as I began to suck him.
"Fuck yes, you look so sexy with daddy's cock in your mouth boy"
His cock was quickly hard, he was probably 7 inches and meaty, I continued to suck him as I arched my back up, almost showing off my ass. I was trying to think of how I watched so many girls and guys in porn suck cock trying to mimic it but it almost just naturally came to me, I started to savor it.
"Yes boy, just like that, such a natural. Keep sucking daddies cock"
His words literally made my cock twitch, and almost drove me to suck him more enthusiastically. I was almost lost in a daze, I knew he was talking to me but I couldn't focus on anything other than sucking his cock and he was right, i did feel like a natural. I was in my groove until he pulled my head off his cock looking me right in the eyes and pulling me in for a deep kiss. he finally broke the kiss looking me right in the eyes.
"You ready for daddy to make you his boy?"
"yes daddy" I honestly wasn't sure what he meant but I was so in the moment I was completely under his spell.
"get on your back, I want ot see that sweet boy hole"
I rolled onto my back as he went to the night side table grabbing what appeared to be a bottle of lube and condoms, as he got between my legs looking my right in the eyes as he poured lube on his cock fingers and slowly pressed one in. I let out a loud moan, shocked at the feeling of something pressing inside me but he began to coach me through it, how to breath what to do and as I relaxed he added another finger and then a third slowly fucking me with this fingers as I moaned like a slut.
"You ready for daddy to fuck you boy hole?"
"Yes daddy, I want you to fuck me so badly"
I couldnt believe how naturally those words flew out of my mouth but I was dying for it, I had built it up for months at this point reading these stories wishing I was experiencing it and now here I am about to finally experience it.
He gave me almost a devilish look as he put a condom on his cock lubing it up more until i felt him press his cock against my hole adn finally press the head inside me telling me to breathe and relax. I couldnt believe how much pressure their was, the feeling of a cock stretching my hole
"OH FUCK" was all I could say over and over, as he put a pillow beneath my lower back.
"Relax boy, you're doing great, take daddy's cock, let me in boy"
My breathing intensefied with the pain as his cock began to press in further and he held his cock there putting his hands down next to my shoulders lowering his face close to mine.
"You're doing great boy, just relax and let daddies cock in" and he planted a kiss on me.
he gave me time to adjust as he kissed me which naturally relaxed me, my hands no longer gripping the sheets but now rubbing his back, which clearly was a sign to him as he slowly started to thrust in and out of me with more of his cock going in each thrust. As he continued to slowly pick up the pace the pain began to subside or at least the pleasure began to grow I began to moan louder and louder.
"You like daddy fucking you dont you boy?"
"Yes daddy, I love it please dont stop fucking me"
He almost had a smirk as he started to really pick up the pace, his muscles almost popping and sweat dripping down them, it was such a hot sight to see as the pleasure grew more and more.
"Fuck, take daddy's cock boy, take that fucking cock"
my hands swung to the side and gripped the sheets as the pleasure began to grow almost to an uncontrollable level, I couldnt believe how intense and sensation was, how incredible it felt, how hot it was to have this older alpha man fucking me. He switched holding my legs up over his shoulders almost getting more leverage going deeper and deeper, I was moaning and whimpering with each thrust.
"You like daddy fucking you like a littel slut boy?" his words becoming more and more dominant
"Yes daddy, please dont stop, fuck me like a slut" my words just naturally becoming more submissive
"Fuck yes, knew I'd have you begging me to fuck you eventually. Such a sexy little slut" After all of this I was still being shocked, how much being spoken down to was turning me on.
"Im getting close boy, I want to cum in that pretty fucking mouth, watching you eat daddy's seed"
"yes daddy, please give me your seed"
I had never really thought much about where I am would cum, I had usually cum by that point and either stopped reading or watching but in this moment I truly wanted him to cum in my mouth and swallow his seed. He pulled from my hole swung over kneeling next to my face, ripped the condom off stroking his cock next to my now wide open mouth.
"Here it comes boy, take daddy's seed"
he erupted grunting and roaring as he put his cock right into my mouth and began to cum, shooting stream after stream of cum into my mouth. I couldn't believe how much he was cumming. he kept going drop after drop falling from his cock into my mouth as I swallowed it all and he knelt there next my head, cum still hanging from his cock, I pressed my mouth up, sucking and savoring every last drop.
"Oh fuck, you are so sexy" as he collapsed next to me, his breathing so heavy coming down from his powerful orgasm.
"You did so good for your first time. I'm definitely going to need more of those holes boy"
"yes daddy, I going to need more of that cock" still riding my high from this hot session as he pulled me in for another kiss.
We laid there for a second before I got up to get going as it was getting late, I got dressed as he stayed naked and walked me to the door, pulling me in for another deep kiss and giving me his number.
"Text me anytime you need some more daddy cock" with a wink as he opened the door to let me out.
As I drove home, coming down the experience I started to question what I just did, "did that really happen? why did I let that happen? did I actually enjoy it or did I feel pressured?" I was a nervous wreck unsure how to handle this experience. I could barely sleep that night knowing I did something I couldn't take back, "did I really want to do that?" but at the end of all of those thoughts Id think about being with him and how hot it was, hot amazing it felt to be fucked like that. I started to relive it in my head, my cock rock hard and I gave it a few strokes and came so hard, harder than i ever remember cumming before.
The next days he was all I could think about, wanting to be his "boy" again, feel him overpower me and use me until he came in my mouth again. I remember that next Friday there was no delivery for him, I was actually feeling sad, I needed to see him again so as I went to my car I had no choice but to text him. I asked if I could come over tonight and I remember him saying he wanted to see if I really wanted to see him again so tested if I'd text him.
When I got to his place that night we were all over each other ripping our clothes off making out barely feet inside his house. We fucked multiple times that night all over his house, every time he'd cum in my mouth and I came while he fucked me, he stroke my cock maybe a few times and I came so hard I literally started to tear up. It was easily the best sex of my life over and over. The next year and a half I was at his place at least once a week being his slutty boy, i loved how he used me, how he treated me. This continued up until I graduated and moved into the city where I continued to explore my sex life mostly with daddies. Whenever I was back home I always tried to find time to go see him.
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