Killua
01/09/17 08:17PM
I said no but uncle mike told me he would give me cookies afterwards..
toonsrule
01/10/17 01:04AM
First couple of times I became intimate with my first real girlfriend I discovered I couldn't maintain a hard on because I got so used to jackin off to porn. It was a bit embarrassing, but she was nice about it and I got her off with my hands. After that I changed my masturbation habits (some edging, fantasizing instead of porn, kegeling) and it worked out. When I'm single, though, I can't bring myself to stay off the porn, so I'm still sometimes struggling with e.d. :[

Anyway, hopefully some young people out there will take this into account if they plan on getting a girlfriend.
GoodAsh
01/10/17 08:18AM
I am one of those rare people who actually kept his promise to keep it in my pants until married. I did not lose my virginity until I was thirty-one years old on my wedding night. Let me tell you, as that very rare person who has taken this path, I do not recommend it. All I have to show for all of that patience is a pornography addiction, a hormone imbalance, and a ruined marriage. Before this post becomes too much of a PITY-ME crapfest, let me give you a spoiler: there's a happier ending.

When I was in my twenties, there were a few opportunities when I think that I could have scored. At one point, I was engaged to a nice girl. She was this tiny brunette thing. She was willing and even interested, but I put on the brakes. We broke up before sealing the deal, and it took me a couple of years to get over her.

When I turned thirty, a met this wild red head. She was smart, nerdy, funny, and sexy. Although my eye tends to wander younger, she was actually older than me by a few years. We got engaged within months, and we were on our way to getting tied up in the old hitch. We moved in together into a tiny house that she rented from her boss. Her boss had just bought the house from another employee who had to move away because her daughter had some sort of drug problem. Waifu couldn't wait to take my virginity. She actually bragged about it to her friends.

The day of the wedding comes around, and I've got this feeling that I am making a mistake...
GoodAsh
01/10/17 08:26AM
...I am waiting for someone (anyone) to tell me not to do this, but everybody is supportive. Even my father who hates marriage says this will be good for me. I figure I just have nerves.

We go through with the (entirely too expensive) wedding. That night, waifu is willing to take it slowly for me, but I am good to go. We were trying to get preggers at the time, so there was no protection involved. Now waifu suffered an injury during her time in the army, and she has a metal hip now. She only wants sex in one specific position which is comfortable for her, and it's damn awkward for me. Nonetheless, I will myself to power through -- or power into. The sex was disappointing for both of us, I think. We figure that it will get better with practice.

After that night, we move back into the tiny house we are renting. I resent the hell out of the fact that we are paying high rent for this place AND doing most of the restoration work for the landlord. Waifu knows it's crazy, but he is her boss, so she demands that we don't complain. Life gets more and more miserable in the tiny house. My porn addiction gets out of control, but we aren't actually having much sex.

Soon, we are involved in these terrible screaming matches. We are both mellow people, and this isn't like us. Waifu finds some porn on my computer which triggers her. It reminds her of her own traumatic memories, and she freaks. She decides to divorce me and move out to state to be near her family. I beg waifu to stay, but she's made up her mind. If she isn't staying, I sure as hell am not continuing to stay in that little house that I hate. I move my divorced ass into a boarding house where I contently rent a room and attend Sexaholic Anonymous meetings for two years...
GoodAsh
01/10/17 08:39AM
...My brother tries to get me out of my funk by setting me up with some chick from where he works. I'm not interested, but I politely tell him that I will consider it. Now understand, I am still serious about my wedding vows and bullheaded enough to remain chaste for the rest of my days. At the same time, I doubt that is what God wants for me. I pray to Mary about this quandary. She answers me. I swear, the Holy Mother actually speaks to me in my mind. These are her exact words,

"I WANT TO YOU BE A MAN AND MAKE A DECISION ALREADY."

Daaaamn, Mary just talked smack to me.

I gave the girl a call. She's a bit younger than me, and she's another short brunette type, just like I like them. She is by far the least crazy woman I have ever dated. A year later, I make her my second wife. Now, I am the more experienced and more prone to initiate sex. Sex is much, much better. Best of all, I am not sticking my dick in crazy anymore.

Later (just a few weeks ago really), something occurs to me. A friend is over at my place, telling us about her next door neighbors. The friend informs us that the house is either haunted or else chemically bad because every family who moves in there turns violent. Our friend mentions something I did not know, that drug labs are supposed to be condemned because harmful chemicals can embed themselves in the walls and ceilings.

Gears begin turning in my noggin. That damn little house; it used to belong to the mother who moved away because the daughter had a drug problem; I and waifu couldn't stop screaming at each other after we moved into that house; we replaced the floors, but we only painted over the walls, and we didn't get around to doing anything with the ceiling. That tiny house was a god damn meth lab, and it was giving us all the bad effects with none of the highs. Even my lowered sex drive might have been a symptom. We were being fucking poisoned. By leaving me, waifu probably saved both of our lives.
Baxter
01/10/17 08:06PM
I lost my v-card behind a watertight bulkhead door on a U.S. Navy aircraft carrier, underway in the Indian Ocean back in the fall of '09. Best. Deployment. Ever. She turned out to be crazy in the end, but it was so worth it.
GoodAsh
01/11/17 12:09AM
I love these stories.
bipface
01/11/17 07:47AM
GoodAsh said:
I love these stories.

I think yours was the longest so far though :P

Reading them does depress me a little, because they make my own life seem so uneventful by comparison.
Cum_Cannon
01/11/17 11:51PM
My first was with a random hook up I met online. She turned out to be a tranny which is something that at the time I was not ready for, so I left pretty unsatisfied. After that was with a coworker after my first gf broke up with me. I was pretty depressed and she made me feel a lot better :)
Clichecaligirl
01/12/17 12:56AM
Thank you all for sharing your stories!
Well... almost all of you. A FEW of those I could have done without reading... ~_~

I think I posted part of this story somewhere on a different thread but this will be more complete...
So when I was 9 this boy moved onto the street behind mine in my neighborhood and within a year we were like the bestest of friends. Unfortunately around when I was 13 my parents split and I went with my dad when we moved away. We were moving around a bit while he was doing a lot of contract work so I was homeschooled for a while, though I did also end up in a mental hospital for a bit but that's a different story.
ANYWAY... He and I stayed in touch thanks to the intarwebz and we played a ton of MMOs and did rp chatrooms and just one-on-one rping a lot and explored a lot of sex and fantasies through that. He got a girlfriend and we weren't quite as close during that but then when we were 16 she and he broke up. He took it REALLY hard, and that coupled with that he has severe clinical depression meant he was really suicidal and was crying himself to sleep almost every night. I was really worried that he was going to kill himself, the summer had just started and his parents were both working so he was at home alone all day. So I worked my butt off to get a bunch of my own school work finished and then convinced my dad to let me go stay with my bff for a month.
Clichecaligirl
01/12/17 01:17AM
The first few days I was there we just talked a LOT. We played some games and watched some movies and whatnot but mostly it was a lot of talking and also kinda getting back into being comfortable with each other since we'd grown apart slightly. He talked some about the sex stuff but he seemed embarrassed to get too into it, and I being a virgin and knowing only porn and hentai and whatever was under the assumption that real sex was COMPLETELY different and way more personal so I didn't push the subject.
Then a few days later I go out to meet some other old friends at the mall and he stays home saying he's fine and he's just going to sleep in or whatever. Well it turns out those friends turned into cunts in the 3 years since I'd seen them... so I found a polite way to excuse myself early and walked back to his place, letting myself in through the back door that he left unlocked. I didn't announce my return because he said he was going to take a nap or whatever and I didn't want to wake up, so I walk into the room and... woo my heart just fluttered remembering it.
I don't remember exactly what he was watching, but he was at his desk watching porn of some kind, and he had the biggest cock I have ever seen in his hand. Like bigger than most porn stars I'd seen. I was just kind of in shock and trying to comprehend the situation, when he noticed I'd walked in and nearly jumped out of his seat before pulling that monster dick back into his boxers and trying to come up with some silly excuse as to what he was doing (like I didn't know. lol).
So I calmed him down and told him come on... I masturbate and watch porn too. We used to rp really detailed sex scenes, it's not that weird. So we started watching porn and touching ourselves together for a few days after that, though to be honest I was mostly mesmerized by that magnificent dick while he was stroking it. Then we were talking one day about sex and he was saying that even near the end of their relationship he was still sleeping with his now-ex because it turned out he was really good at sex and it made him feel good to please her, though he was now pretty sure she only stayed with him as long as she did because of the sex. So being the dumb, naive sweetheart I was I suggested "Hey well you can have sex with me and then maybe that'll make you feel better about yourself and you won't be so depressed!" I know. How'd I get so smart.

Well it started out how many of your stories start, we tried touching each other while watching porn instead of just ourselves. Then we went to oral, and I learned I cannot deep throat no matter how much I wanted to, I could only get maybe 3 inches of that monster into my mouth and still had to use both hands on the rest of his shaft.
(ack i gotta run, to be continued!)
KingOfTrolls
01/12/17 01:19AM
İve fuck prostitute. She was blonde one hot bitch.
Bigasses
01/12/17 08:13PM
Clichecaligirl said:
The first few days I was there we just talked a LOT. We played some games and watched some movies and whatnot but mostly it was a lot of talking and also kinda getting back into being comfortable with each other since we'd grown apart slightly. He talked some about the sex stuff but he seemed embarrassed to get too into it, and I being a virgin and knowing only porn and hentai and whatever was under the assumption that real sex was COMPLETELY different and way more personal so I didn't push the subject.
Then a few days later I go out to meet some other old friends at the mall and he stays home saying he's fine and he's just going to sleep in or whatever. Well it turns out those friends turned into cunts in the 3 years since I'd seen them... so I found a polite way to excuse myself early and walked back to his place, letting myself in through the back door that he left unlocked. I didn't announce my return because he said he was going to take a nap or whatever and I didn't want to wake up, so I walk into the room and... woo my heart just fluttered remembering it.
I don't remember exactly what he was watching, but he was at his desk watching porn of some kind, and he had the biggest cock I have ever seen in his hand. Like bigger than most porn stars I'd seen. I was just kind of in shock and trying to comprehend the situation, when he noticed I'd walked in and nearly jumped out of his seat before pulling that monster dick back into his boxers and trying to come up with some silly excuse as to what he was doing (like I didn't know. lol).
So I calmed him down and told him come on... I masturbate and watch porn too. We used to rp really detailed sex scenes, it's not that weird. So we started watching porn and touching ourselves together for a few days after that, though to be honest I was mostly mesmerized by that magnificent dick while he was stroking it. Then we were talking one day about sex and he was saying that even near the end of their relationship he was still sleeping with his now-ex because it turned out he was really good at sex and it made him feel good to please her, though he was now pretty sure she only stayed with him as long as she did because of the sex. So being the dumb, naive sweetheart I was I suggested "Hey well you can have sex with me and then maybe that'll make you feel better about yourself and you won't be so depressed!" I know. How'd I get so smart.

Well it started out how many of your stories start, we tried touching each other while watching porn instead of just ourselves. Then we went to oral, and I learned I cannot deep throat no matter how much I wanted to, I could only get maybe 3 inches of that monster into my mouth and still had to use both hands on the rest of his shaft.
(ack i gotta run, to be continued!)

I am sooo glad to see this thread is still alive! And wow, nice stories from all of you, cant wait to hear the continued version
GoodAsh
01/13/17 07:03AM
Hey KingofTrolls, you have me curious. How much did a hot blond prostitute cost you?

Hey ClicheCaliGirl, you have me salivating. I think I am ot the only one. We all anxiously away the climax (pun intended) of your story.
Clichecaligirl
01/14/17 10:36PM
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
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