how i met my Daddy and lost my virginity last year [m/M] [18] | 2016

hi. so ummm this the story of how i lost my gay virginity. i’ve been into guys my whole life but i could never accept it until midway through high school. i didn’t want to be gay, i was so afraid of how hard my life would be and how much i would be made fun of and bullied. i’m not very masculine at all, i’m only 5’5, and really small. i remember being so insecure changing in the locker room when i was younger, and all the bigger boys had already started going through puberty. they were showing off their pit hair and talking about their pubes and how much their penises had grown over the summer. i didn’t get any pubic hair until i was 15, and my penis never grew much - i’m only four and a half inches erect. i felt so ashamed about my body and my sexuality for so long, and assumed everyone knew i was secretly gay and too cowardly to come out of the closet. i went to a small school with about a hundred kids per grade, and only five or six kids were openly gay during my entire time there. there was no one i could date, no one i could talk to. i was miserable. so i spent a lot of time at home alone where my fantasies and desires grew and grew. in the middle of my senior year at the start of 2015, right after I turned 18, i saved up enough money to buy a buttplug for myself. but of course i wasn’t brave enough to go into a sex shop - i gave my mom the cash and asked for her credit card, lying that i was buying school books for the second semester. I made sure to answer the door when the package was dropped off, and I ran up to my room and hide it under my bed. i waited hours after my parents had fallen asleep to take it out and play with it. i went on reddit and looked at porn and read some of the stories on here while i massaged my tight little butthole with the tip of the plug. it took me two weeks to get it all in, and when i finally did, i made up my mind about something i’d been thinking about for a long time. i was going to go online and find someone to take my virginity.

i’ve always been really into older guys and BDSM. I’m naturally very submissive, and for years I masturbated to the image of my middle school gym teacher taking me into his office after school, locking the door behind us, and introducing me to every aspect of gay sex. how i would grind against his bulge with my bubbly little ass, both of us wearing thin gym shorts. how i would get down on my knees, look him in the eye as i pull his shorts down, and say “thank you” right before i grip his thick cock and guide it into my mouth. i imagined him taking me to his house for the weekend and doing my first role-play, where i would be collared and leashed and submit to his will. i was willing to do anything to prove what a good little sub i could be. i imagined changing into panties and slutty outfits for him, and dancing like a stripper in front of him before lying on the bed and spreading myself for his pleasure. “daddy, daddy” i would moan the whole time, “daddy daddy oh my god take me daddy.” I was obsessed with the idea of having a Daddy. it was so so so hot and i felt if i found the right man, i would finally begin to feel comfortable in my own skin, because he would make me feel safe and confident.

I turned 18 in February 2015, and two weeks later i made a Grindr account and started looking on Craigslist. after reading reddit and other sites for a long time, i knew what was safe and what wasn’t, and how hard it could be to find someone truly meaningful to you online. i started talking to guys on Kik and Grindr just to get to know myself and my sexuality. i talked to a lot of really amazing people that helped me understand my sexuality better. i was, and still am, really into cross-dressing, and i’d taken hundreds of pictures of myself in panties and short skirts and thongs that i borrowed from my sister, who had been away at college for two years. Craigslist seemed kind of gross and weird to me, so I didn’t make an ad for a while, but when I finally did, i got almost a hundred emails in two days. it was unbelievable. i posted what kind of person i was looking for along with the ten best photos of my body. almost everyone gushed over my ass and how cute and round it was. i have very little body hair, but i had shaved what little i did have and it really made the difference. reading all those responses, i felt the most incredible wave of horniness and dirtiness wash over me. i read every email i got and eventually narrowed my pool down to six, which made me feel like even more of a whore, like what kind of 18 year old boy is talking to six different guys in their forties, fifties, and sixties and trying to decide which to sleep with?

six quickly became two which quickly became one, and by the end of that week i was pretty much decided on one guy. i won’t say his name, not that it matters - in my mind, all he was was Daddy. he was just like my old gym teacher: stocky, muscular, and super hot. during the week that we talked online, i told him everything, what i wanted, and how i felt about myself. not only was he totally on the same page as me in terms of kinks and interests, he was incredibly supportive and the opposite of intimidating. i started to feel safe for the first time in my life. i told him my longtime fantasy of spending a weekend at my Daddy’s house and being introduced to gay sex and BDSM step by step. he loved it, and would write the most erotic responses to my fantasies, and asking every step of the way if i was comfortable and having fun. i was. i really, really was.

spring break was right around the corner, and i told my parents i was going to the beach with my friends. they were really happy that i was finally getting out of the house and socializing with my peers. i don’t think they could take what i was really doing, but ultimately, i know they’d be happy for me. i was to be picked up by my Daddy just four blocks from my house, and we would drive to his house half an hour away, and begin my training. i told him i didn’t have any toys except my buttplug - he assured me it was ok, that he had everything i would need. i woke up that morning and resisted the urge to masturbate, wanting to save it for my Daddy. i said goodbye to my parents and walked to the bus stop where we said we’d meet. my heart was pounding the whole time, and i got there ten minutes early. luckily, it was deserted, and i spent those long ten minutes thinking about my whole life and how it had all led up to this point. i was excited and incredibly nervous, but when he pulled up to the curb and rolled down the passenger side window to say hello, i fell into something. it was something new, and from then on it all came naturally.

i got in the car and said hi really quietly. i noticed my voice was different than usual - higher pitched. he asked me how i was doing and before we pulled out, he asked me if I was absolutely sure i wanted to do this. i nodded my head vigorously and said “yes yes yes yes” over and over. he put his hand on my thigh and said “it’s okay. you can relax now. i’ll make you feel comfortable and safe every step of the way. okay?” i turned my head slowly and nodded at him, lost for words and a thousand times hornier than i’d ever been. as we drove through suburban streets and eventually got onto the highway, i gyrated in my seat and let out several involuntary moans. Daddy turned to me and said “it’s okay. relax. you’re safe now. you can tell me anything.” something in me changed because i immediately turned to him and asked if i could feel his cock. We were on the highway now and without taking his eyes off the road, Daddy gripped my wrist and put my hand on his thick bulge, barely contained by his athletic shorts. i moaned like a porn star while slowly massaging the first cock of my life. i was hypnotized, and i stroked him over his shorts for ten minutes as we coasted down the highway. all i could say was “thank you, thank you, thank you” over and over again, and for the first time, he corrected me and showed me some force. “‘thank you, Daddy’ you mean.’” i moaned and said “yes Daddy, yes Daddy.” “Yes Daddy what?” “thank you.” “For what?” “….for letting me stroke your cock.” He exhaled, satisfied, and said “very good. you’re welcome.”

When we got to his house, we pulled into the garage and stayed in the car until the door closed behind us. In the dark, Daddy waited several seconds before turning to me and asking me if I was ready. “yes Daddy, i’m so ready. i’m so ready to learn.” He smiled and said I was off to a great start. We got out and he took me by the hand as we entered his house. as soon as we entered the living room, Daddy turned to face me and put his hands onto my shoulders. He gripped them and i looked up into his eyes, totally his. “we’re going to be here for a while. i want you to get on your knees and submit to me now.” he opened a cabinet and got out a padded collar and put it right in front of my face. “this is your collar. it represents your complete submission to me and my will. you become my property while this is around your neck. it is your decision to put it on, but once it’s on, only i can remove it. do you understand?” I nodded and mewled “yes, sir,” like so many of the female porn stars i dreamed of being for years. “Good. Are you ready to learn?” I repeated “yes, sir” and he handed me the collar for me to put on. I wrapped it around my neck and looked up to him as I tightened it, and felt such shame and embarrassment when he grimaced at me and forced me to my knees by pushing onto my shoulders. I had already forgotten one of his commands. “Listen to me. Can you do that?” with the collar fastened around my neck and my hands on my knees, I whispered “yes, Daddy.” He lifted my t-shirt off and asked me what I wanted to do. his cock was staring me in the face and getting bigger and bigger every second. i said “i want to suck your cock” very quietly. “Excuse me?” I blushed, and repeated myself. Daddy smiled and said “Good boy” as he pulled his shorts down and stuck his thick cock right in front of my face. I looked up at him, said “thank you,” and raised my hand to grip him. his shaft was thick and grew stiffer and stiffer as i slowly stroked him, all while looking him in the eye. he had a big smile on his face, told me i was doing good so far, and he gave me permission to take his cock in my mouth. i felt my asshole clench as i breathed in and said “thank you, Daddy.” i turned my eyes to his cock, still growing bigger and bigger. i looked back up at him and said “i don’t think i can fit it all in my mouth,” paused, looked down at it again, and then looked up and said “but i think i’ll try.” with that, i closed my eyes, opened wide, and accepted the head of his penis into my mouth. i moaned immediately, moving no farther than the head, moving my tongue around as if i were massaging it. Daddy let out a sigh and gripped the back of my head. “you’re so good, baby….ahhhh fuck that feels so good.”

this is a lot longer than i thought it would be :p. should i continue? there's so much more to talk about...