This is the true story of my first time having sex (with anyone) when i was a few months into my 18th year. I tell it exactly as it happened, with no embellishment or editing so some things might seem crude, I guess life is like that sometimes :-)
It was the summer of my 18th birthday and until then I’d always been attracted to girls. I wasn’t very good at talking to them but being not too bad looking they still seemed to like me and even though I was still a virgin I’d had a few kisses here and there.
Early in the summer I had stumbled upon the « erotic » section of a local ads website when looking for games to buy, and when I clicked on it I for some reason went to the « men looking for men » section.
I had read a few ads and then had started to come back regularly to read fresh ones.
Call it boredom or hormones or curiosity or whatever else but for some reason I eventually made an account and started posting my own ads. At first they were kinda tame, I didn’t know the vocabulary or anything, but as the weeks passed and I learned more (and started watching some gay porn as well) I began to be more descriptive. Eventually I posted an ad that became quite successful and got a lot of people’s attention (and a lot of answers in my email inbox). It was along the lines of « 18yo bottom teen looking for daddy for my first time » with a few pictures of my slim body and my smooth ass in one of my sister’s lace panties.
I ignored almost all of the answers, I mostly enjoyed the attention and the feeling of being wanted but I had no intention of doing anything because I knew I was straight.
There was however one answer from a 57yo man (we’ll call him J-M) in my town that grabbed my attention. He seemed to know exactly how to talk to me to turn me on. It’s like he knew every one of my deep desires and kinks and the way he spoke to me in that email made me incredibly horny. I’d keep coming back to it and jerking off reading it, only to then feel horrible shame as soon as I came and delete my email account.
Using outlook meant that I had 30 days to change my mind, however, and without fail I would always reactivate it and go back to do the same thing after a few days.
Eventually I answered his email (I don’t remember what I said) and added a few more pictures of my ass for good measure.
He answered back and we went back and forth like that for a bit, him telling me dirty things and showing me his old dick and selfies of his big belly (he wasn’t attractive but that somehow made it better for me???), and me answering him and sending him nudes.
He kept offering to meet me, even inviting me to his vacation home and on holiday and everything but being straight I always said no and changed the subject.
It went on like this for about a month until one night everything accelerated.
I had gone out with my friends for a few drinks but a few turned to many and a couple of joints added in the mix. I always got incredibly horny when I drank and smoked and that’s often when I would take the nudes and email J-M.
That night however I did something that changed my life forever. To this day I don’t know what I was thinking but whilst walking home at 1am I sent him an email with the localisation of the entrance to my street, with a message saying « if you come pick me up right now you can fuck me » and my phone number.
Turns out he wasn’t one to miss an opportunity and he was still awake. Within minutes I got a text message from an unknown number that simply said « on the way. »
My heart started racing but being drunk and high I realized it was mostly excitement, any thought of danger or consequences was far away from my mind.
I waited around for about 30 minutes on a bench near the localisation I had sent him when finally a car pulled up and stopped. I waited for a minute but since he wasn’t moving or getting out and it was 1:30am I figured it had to be him, I walked up to the car and got in on the passenger seat.
He greeted me politely with a smile and started driving right away, when he did the door locked automatically which made my heart jump. The drive was awkward to say the least, we exchanged no more than 2-3 words as I sat there in silence suddenly shy and he just drove in silence as well. At one point he did reach his right hand out and start touching my private areas through my shorts. After a couple minutes he stopped.
Finally after about 30 minutes (that felt much longer) we turned on a small road and drove to a somewhat remote farmhouse. I was pretty anxious at this point, he parked and we both got out without a word. He then smiled at me and said « don’t be shy come on in » and pointed to a door off to the left of the house. I followed him in and realized it led to the basement. I got scared but my fight of flight reflexes are shit turns out and I just silently followed him in. He took me to a bathroom and started undressing me, then himself and then said « we should get clean first ».
We got in the shower and we did. He washed me, spending a lot of time groping my ass and rubbing by asshole which made me go from scared to excited again. I in turn got out of my shell just a little and took his dick in my hand and jerked it a little bit. He got quite hard but to my disappointment his dick was fairly small, maybe 10cm.
When we were done we got out and he dried me, he then got dressed and as I was about to do the same he told me no need and to just follow him. He headed for the front door and I froze in front of it realizing he wanted me to go outside naked. He turned, saw me and just said « it’s 2am and there’s no neighbors here, no need to worry ». Somehow that worked and I followed him outside, naked as the day I was born.
Luckily for me we headed straight for another door to the right of the first one and we were in again on the ground floor within seconds of going outside.
The door led to a corridor with a kitchen on the left, living room on the right and then further along a bedroom on the left and a bathroom on the right. He led me straight to the bedroom.
Once we were in he told me to get on my knees and I obeyed. He undressed again and brought his dick to my lips but when he pressed against them I didn’t open my mouth. Part of me wanted to but I guess I’d sobered up a little and part of me rejected the idea. He simply said « that’s okay no need to rush things » and turned around. He grabbed a paper from the desk and walked back to me. He handed me the paper with an explanation « look it’s a test from last week saying I don’t have any STDs, this means I can fuck you raw. »
Still naked on my knees with this imposing man standing in front of me I simply took the paper and looked at it. I couldn’t make sense of it but simply said « yes okay, promise it’s real ? » to which he replied « trust me ».
He took it from me, put it back on the desk and told me to lay on the bed on my back, an order I promptly obeyed. At this point I realized I wasn’t in control of my own body anymore, I was simply obeying commands and there was very little thoughts going through my mind.
He grabbed my thighs and placed me to his convenience, my butt flush with the edge of the bed, on my back with my legs in the air and my feet resting on his shoulders. He then grabbed a bottle of lube that was on the bed, poured some on his fingers and started spreading it on my hole. After rubbing it for a minute he slowly pushed one of his fingers inside me, and I squirmed. He shushed me and kept it there for a few seconds, and then took it out. I then looked at him pour some more lube onto his fingers and spread it on his erect penis. Once that was done, he looked into my eyes and then at my spread butt cheeks, and without saying a word he positioned his dick against my asshole and pushed it all in in one swift motion. At first it hurt like hell, like lightning inside my ass, and I was surprised because his dick was pretty small so I didn’t expect pain at all. I yelled out and he just kept it all the way in for what felt like ten minuted although it was probably much less. Eventually I felt my hole relax around his dick and the pain slowly went away. I guess he noticed that I wasn’t so tense anymore because that’s when he took it out, which hurt once again. Not one to give me a break, he instantly put it back all the way in.
At this point my mind went blank and I just closed my eyes. I felt him start to go in and out, then speed up and after a few minutes he was fucking me vigorously. I suddenly let out a moan, shocked, I realized that the pain was gone and I was enjoying this. I opened my eyes and saw him with a grin on his face, obviously happy with himself. He started fucking me harder and I just stared at his big belly slamming into my private parts (I couldn’t make out his dick going into my ass), sometimes looking up at him to see him staring at me.
Just as I was starting to get out of my state of shock and enjoy the experience, I saw his facial expression change and felt him tense up. A panic went to my heart as I realized he was about to cum inside me without a condom. A million thought raced to my mind, HIV, STDs,… but it was too late: he let out a groan, forcefully pushed his dick as far as he could inside me once, then twice and then kept it there. I felt something warm inside my ass, and a lot of it. He had just come.
I simply froze in place and looked at him, he came back to his sense slowly and pulled out, at which point I felt a stream of cum come guzzling out of me. Still frozen inside I didn’t even think of wiping myself clean, I crawled up higher into the bed, got on my side and closed my eyes as he went to the bathroom. I didn’t sleep however, I just didn’t want to face to situation just yet.
When he came back into the room I sat up and asked « could you bring me home now? » to which he said « it’s 3am it’s too late, I’ll bring you back in the morning okay? ».
His voice was soft and friendly but I didn’t really feel like I had a say in the matter, I simply laid down on my side again and closed my eyes, exhausted. I fell asleep.
I’m guessing he went to sleep next to me, but what I know is that he didn’t sleep for long and me neither. I don’t know how long had passed but I got woken up by the feeling of him pushing his lubed up dick against my ass. I woke up but kept my eyes closed, adrenaline cursed through my veins. Still pretending to be asleep, I laid there on my side as I felt him slowly push his dick inside me, he then grabbed my hip with his hand and fucked me from the side. My mind was racing, I was quite sober by now and this 57yo man I had never met before was fucking me whilst (he thought) I was asleep, using his own cum that was left inside me as lube. Just a few hours prior I was a normal straight teen with crushes and flirts and now I was being used raw by this old man without him even bothering to wake me up or ask me consent, as if I was a fuck toy.
After a few minutes of using me, I felt him tense up again and he sped up the pace, then proceeded to cum inside me once again. He pulled out and this time something inside me told me to clench my butthole and I managed to keep most of the cum inside. Apparently aware that there was no way I could have slept through this, he said « good boy » and rolled back to sleep. I hate to admit this to this day but it made me feel proud and warm inside, sign of things to come I guess.
I went back to a state of semi sleep, but couldn’t really sleep profoundly, having too many thoughts in my head. A while passed and then suddenly I felt him wake up, I heard the sound of lube being squished out of a bottle and I felt him position himself behind me. I didn’t move but opened my eyes this time. He pushed his dick against my hole but didn’t go in, he just rubbed it on my asshole for what felt like forever and suddenly something came over me. Sick of being teased I reached around with my right arm, grabbed his dick and guided it to my hole. Obviously very happy with me he let out a moan and pushed it inside, my hand still guiding its course. My job being done I took my hand back and he started fucking me harder than ever before. Barely a few minutes had passed when once again, he emptied himself inside me with a loud moan. Now used to it (already), I clenched as he pulled out and little of his sperm came out of me.
We both went back to our (probably semi-)sleep and all I could think about was how I had been fucked three times already and I had somehow gone from scared to wanting more. Luckily for me he was insatiable and before long I felt him move again. This time the slut in me really woke up and not willing to wait I reached around, looking at him, and guided his dick straight to my hole. He started fucking me and after just a few strokes inspiration struck me, I reached between my legs and cupped his balls with my right hand. He let out a yell and I thought I had hurt him but turns out I had made him feel too good because he came instantly as I used his balls to pull him deeper inside me. He had been fucking me for maybe 30 seconds. As he came back to his senses he didn’t hesitate to make his feelings known and simply said « that was great but next time ask first you whore ». I felt a buzz inside me.
By that time I realized the sun was about to come up because I could see light coming in through the curtains. I laid there for a bit and after maybe an hour of nothing happening it was fully day out. I sat up on the bed, and doing so realized there was quite a mess on the mattress behind me. He was awake because as soon as I sat up he said « not so fast ». I turned to look at him and he told me to lay down again like before. I did as I was told, expecting him to fuck me once more but to my surprise he instead reached around with his arm and grabbed my limp dick. Taken aback I didn’t move and he started stroking it. I suddenly felt intense fear, remembering the feelings of shame and disgust that came over me after I would come to gay porn or emails and thinking just how much worse it was going to be if I came still full of another man’s cum.
Unable to move, all I could do was lay there while he masturbated me. After a few minutes of this, biology did its thing and I felt that I was going to cum. It was an intense release physically, like rarely before but it didn’t feel good emotionally. Instantly I felt such shame and regret, I couldn’t move I was frozen in place. When he felt me cumming he cupped his other hand in front of my dick, leaning over me. He managed to catch most of my cum in his cupped hand and I was now not only frozen and disgusted but confused too, what was he doing?
I got my answer soon enough, he took my cum, spread some on his dick and the rest in my own asshole and pushed his dick inside me. He was using my cum as lube to fuck me.
« That is evil » I thought to myself, between shame, disgust, regret and begrudging pleasure at the feeling of being used again.
He soon came and then told me to go wash up.
I got up machinally and walked to the bathroom, I sat on the toilet and suddenly what felt like liters of cum came streaming out of me. Once I was done I wiped myself clean and walked out. He had laid my clothes folded neatly on the bed but wasn’t in the bedroom anymore. I got dressed and walked out into the corridor and that’s when I saw him all dressed in the kitchen.
The morning turned to weird as he kindly offered me breakfast, not saying a word about the night we had just had. Somehow that worked for me too because I politely refused breakfast and he said « okay then if you want we can drive back to your place, I’ll drop you off there ». I agreed and we walked out of be house and got in the car.
We drove in silence for about half an hour, and when we pulled up to my street I noticed that it was already past 9am. He stopped the car, and as I went to open the door I found it still locked. I looked at him, puzzled, and he smiled and reached for his wallet. As if it was the most normal thing in the world, he pulled out three 100$ bills, handed them to me and simply said « you earned it kid », unlocking the door as he said it. Shocked and confused, I simply grabbed the money, put it in my pocket and got out of the car.
I walked the five minutes to my house without a thought in my head, got inside and luckily didn’t run into anyone. I got in the shower, showered for what felt like an hour, then got out and passed out in my bed, still naked, sore and exhausted.
(PS: I still have those pictures from the ad that led to this, if anyone is interested don’t hesitate to email me I’ll send them to you :-))
