Clichecaligirl said:
Glad you guys like my story! Alright where was I...

So my friend has ridiculous depression and body issues and insisted that he wasn't that big, and anytime I even mentioned a ruler he would get soft, so I waited until one morning he was asleep and had morning wood and I measured him at like 11" long and 6" around. He still doesn't believe me, but that got me really horny just knowing that for some reason... SO I decided I wanted it in me, and I got some lotion and started covering his cock with it and he woke up to me with my hands all over his shaft... confused at first but he got into it quickly. I was just wearing a big baggy t-shirt of his and had taken my underwear off so nothing else, and I got on my side with my back to him and held his shaft and pulled it to me. I wasn't on any kind of birth control and I was only 16 at the time so I was determined to get that thing into my ass.
Lucky for me he was a bit nervous, and that got him a little less than fully hard, so I didn't have to take that huge monster all at once on my first try. I'd fingered my ass before so it wasn't entirely new but I'd certainly never had anything quite that thick or long inside it.
There was a little pain and difficulty at first but luckily no major damage was done. I guess that's why I like this picture so much... rule34.xxx/index.php?page=post&s=view&id=1711043
The same position and that giant cock in her ass reminds me of my first time. Well... first time being penetrated.
SO we did anal and oral a lot... then I had to go back home for a while. So I was on the phone with my cousin one evening and I was telling her all about it (she and I are pretty close) and she somehow said something out loud about my bff putting it in my butt. Well unfortunately (and I didn't learn this until more than a decade later) her little sister was standing outside her bedroom door listening, and she ran downstairs and asked her parents what my bff would possibly want to put in my butt and why... and then they called my dad. -_-
So a few days later my dad sits me down and tells me I'm a beautiful young girl who's going to be getting a lot of attention from guys (I was going to be going to actual high school when the summer was over, no more home schooling) and he didn't want me to make any mistakes that might make my future more difficult, so he was going to put me on birth control. I thought he was just being really progressive, I had no idea he was doing it just so I'd stop having anal so much.
Well it didn't stop me at all. lol
So I got on the shot and next time I went to visit my bff he took my virginity. That was MUCH more painful, and luckily again he was worried and wasn't fully hard. Then we had a bunch more anal while I recovered and then went back to trying vaginal again. Eventually I was relaxed enough and stretched enough that I came, and that feeling made me realize I had already been having orgasms from the anal, so I realized I was analerotic (able to come from anal, duh).
My absolute favorite was to let him fuck my cunt until I came and got his cock soaked with my juices, then grab his cock between my legs and push it into my ass, using my own juices as lube. Something about that was really hot to me. We spent a LOT of time just imitating things we saw in porn. It made sense to us... I was a large-breasted blonde and he was a guy with a huge dick... so why wouldn't we be able to do stuff they did in porn? We fucked in every position we could find and tried everything. UNFORTUNATELY I have trouble getting off from toys so I never really got to enjoy being DPed, and it's near impossible finding another partner who would share me and won't get jealous of him because of his size.

Sadly this story doesn't have the happiest of endings... we were young and confused and thought that sex had to = relationship. So we tried being together for a while and it got awkward because we really didn't connect on a romantic level, just as friends and on a sexual level... So we stopped talking for a long time. The good news though is we connected again in our early 20s and we've been friends again since. We're both busy with our jobs but I still try to go visit him or he comes to me at least once a year and gives my ass a nice pounding. Last year we even got really crazy and did a show on chaturbate. Made like 200 bucks in one night. lol

Clichecaligirl said:
Glad you guys like my story! Alright where was I...

So my friend has ridiculous depression and body issues and insisted that he wasn't that big, and anytime I even mentioned a ruler he would get soft, so I waited until one morning he was asleep and had morning wood and I measured him at like 11" long and 6" around. He still doesn't believe me, but that got me really horny just knowing that for some reason... SO I decided I wanted it in me, and I got some lotion and started covering his cock with it and he woke up to me with my hands all over his shaft... confused at first but he got into it quickly. I was just wearing a big baggy t-shirt of his and had taken my underwear off so nothing else, and I got on my side with my back to him and held his shaft and pulled it to me. I wasn't on any kind of birth control and I was only 16 at the time so I was determined to get that thing into my ass.
Lucky for me he was a bit nervous, and that got him a little less than fully hard, so I didn't have to take that huge monster all at once on my first try. I'd fingered my ass before so it wasn't entirely new but I'd certainly never had anything quite that thick or long inside it.
There was a little pain and difficulty at first but luckily no major damage was done. I guess that's why I like this picture so much... rule34.xxx/index.php?page=post&s=view&id=1711043
The same position and that giant cock in her ass reminds me of my first time. Well... first time being penetrated.
SO we did anal and oral a lot... then I had to go back home for a while. So I was on the phone with my cousin one evening and I was telling her all about it (she and I are pretty close) and she somehow said something out loud about my bff putting it in my butt. Well unfortunately (and I didn't learn this until more than a decade later) her little sister was standing outside her bedroom door listening, and she ran downstairs and asked her parents what my bff would possibly want to put in my butt and why... and then they called my dad. -_-
So a few days later my dad sits me down and tells me I'm a beautiful young girl who's going to be getting a lot of attention from guys (I was going to be going to actual high school when the summer was over, no more home schooling) and he didn't want me to make any mistakes that might make my future more difficult, so he was going to put me on birth control. I thought he was just being really progressive, I had no idea he was doing it just so I'd stop having anal so much.
Well it didn't stop me at all. lol
So I got on the shot and next time I went to visit my bff he took my virginity. That was MUCH more painful, and luckily again he was worried and wasn't fully hard. Then we had a bunch more anal while I recovered and then went back to trying vaginal again. Eventually I was relaxed enough and stretched enough that I came, and that feeling made me realize I had already been having orgasms from the anal, so I realized I was analerotic (able to come from anal, duh).
My absolute favorite was to let him fuck my cunt until I came and got his cock soaked with my juices, then grab his cock between my legs and push it into my ass, using my own juices as lube. Something about that was really hot to me. We spent a LOT of time just imitating things we saw in porn. It made sense to us... I was a large-breasted blonde and he was a guy with a huge dick... so why wouldn't we be able to do stuff they did in porn? We fucked in every position we could find and tried everything. UNFORTUNATELY I have trouble getting off from toys so I never really got to enjoy being DPed, and it's near impossible finding another partner who would share me and won't get jealous of him because of his size.

Sadly this story doesn't have the happiest of endings... we were young and confused and thought that sex had to = relationship. So we tried being together for a while and it got awkward because we really didn't connect on a romantic level, just as friends and on a sexual level... So we stopped talking for a long time. The good news though is we connected again in our early 20s and we've been friends again since. We're both busy with our jobs but I still try to go visit him or he comes to me at least once a year and gives my ass a nice pounding. Last year we even got really crazy and did a show on chaturbate. Made like 200 bucks in one night. lol