Mine was, you guessed it, in High School. I used to date this girl who was a year younger than me. We lived in the same neighborhood so I took her to and from school. I was, and still am, a virgin and she had been with one guy before I dated her. She would never say who he was, only that she wished she had waited for marriage. So she made me wait until we got married.
I did persuade her to let me eat her pussy and later her asshole. The entire time I dated her I didn't masturbate out of respect for her. So the entire time I was with her I was pretty much blue balled.
Once she got hooked on me giving her oral sex, it was practically all we did. I would take her home from school and she would shower at my house (she had gym last period and showering was optional) and then we would watch General Hospital until 4:00. Then I would go down on her until 5:30 and then take her home before her parents got there. Because she got more and more into me eating her out, she gradually skipped the shower and had me eat her during General Hospital. I would pretty much be eating her out for almost three hours a day. Her pussy was always sweaty from gym class and I loved the musky taste. I'd lick her sweaty ass crack and asshole too.
During the summer, she went off to her church camp for 4 weeks. When it was time for her to come back, her parents were on a vacation of their own and her sister couldn't get off work so they had me pick her up. I drove almost an hour to pick her up. When I got there she was nowhere around. I asked about her and this girl said she was probably with Adam.
I waited at the car for 20 minutes or so before she came up the path arm in arm with some dude. She didn't see me and so she kissed him deeply, with tongue and his hand cupping one of her tight butt cheeks. My dick got instantly hard. I quickly got in my car and watched them. She finally broke their embrace and walked toward the parking lot. When she saw my car, she stopped. I could tell she was totally shocked to see me there. She finally came to my car and I got out to open the door for her.
She hugged me and kissed me on the cheek. "I'm surprised to see you."
I explained the situation as she got into my car. I had the windows up because I was running the AC. She quickly rolled down the window but I could smell the sex on her. It was very strong. Her lips were swollen from kissing. My dick was rock hard again.
As we drove, I asked her, "Could we find a place to pull over. I have to eat your pussy. I've missed you so much."
"No. I need to shower."
"I don't care if you shower. It's never stopped us before. Please, I need to taste you."
"No. I don't feel like having you do that in the car. Wait until we get to my house. I can shower and you can do that for a long time since my parents won't be home until late tonight."
When we got to her house I begged to be allowed to eat her before she showered. I told her I would be her slave for a month (a game we sometimes played was me being her slave). Finally she relented. Her panties were crusty and still a little sticky. Her pussy was ripe. It smelled pretty strong of sex. I dove in and ate her. Up close I could tell her pussy was very different. It was stretched out and loose. I pressed my face into it and sucked with everything I had. She was going wild. She told me how much she missed me eating her.
Then she let it slip. "Adam won't do this." She slammed her hand over her mouth.
I looked up from between her legs and asked "Is he that boy I saw you making out with?"
She was shocked. "You saw that?!"
"Yes." I answered and began eating her some more.
She didn't know what to say, so she just shut up and enjoyed my oral attention.
When I had eaten her for a few hours, she finally stopped me to go take a shower. She smirked at me a little when she saw how messy my face was. "You might want to wash your face."
When she got done showering, we cuddled a little. I was feeling very submissive towards her and I asked her if I could kiss her feet. This was something we did when I was her slave. "Of course."
As I licked and kissed and sucked on her toes and feet I asked her if she cheated on me with this Adam. She didn't answer. "Please tell me. I won't be mad. I love you so much that I don't even care if you cheated on me."
"Yes. I cheated on you with him. He's the guy I lost my virginity to last year. I couldn't resist him. I'm so sorry."
"Does this mean that you and I could have sex?"
"No. I still want to marry you and I still want to wait until were married. I was just weak. He lives kind of far away so I shouldn't be tempted until next year."
All the time she's confessing, I am increasing my worship of her feet. I stopped long enough to ask, "Did you suck his dick?"
"Yes. He really likes that."
"Do you think you could suck mine?"
"No. Sorry, but that is something you will have to wait for."
"Did you have sex with him?"
"Yes. Lots of times."
"How many times?"
"I don't know. He brought a dozen condoms and we went through them in the first few days. Maybe 80 times? It's hard to say."
"So you had sex with him with no condoms on?"
"Yes silly. I told you we ran out of condoms really fast."
"Did he come inside you?"
"Yes. Every time unless he came in my mouth. I am on birth control."
"Did he fuck you before I picked you up?"
"Yes. In fact, we were doing it probably while you were waiting in the parking lot."
"Did he come inside you?"
"And you let me eat you out without showering?"
"You were so insisting, I got tired of telling you no. Plus it was so hot you eating me an hour after Adam got done fucking me and coming inside me."
I faked like I was upset and went home. As soon as I got there I ran into the bathroom and pulled my dick out and started jacking off. I came in mere seconds and it was such a great orgasm that I nearly screamed.
She dumped me pretty much right after that. She still got me to take her to school. Adam's man took a job in our city and she started dating him immediately. I still managed to eat her pussy from time to time because he wouldn't do it. I never got a true creampie from her, but she planted the seed of cuckoldry in my head and I wouldn't have it any other way.
I'm not sure if it was the last semester of my senior year, or if it was that summer. I know during that February of that year was when I realized I was into chastity, and I also realized that the feelings I had been having for the last 15 months or so were officially submissive. Anyway, I had a girlfriend from June of my sophomore year until February of my Junior year. We lost our virginity to each other, broke up, and a few months later she started fucking other people and I was obviously still in love with her. At this point all I knew was that I had a foot fetish and that I was slightly submissive and liked a little teasing.
However, she and a group of girls we always hung out with became pretty slutty, and it became the weekend thing to get takes and... well, be slutty lol. We did the same things and hung around the same people, so we were always together. The first few months after we broke up was alot of fighting, but eventually we became best friends. Now that I look back on it, if I had been a little more mature and found out more about myself sexually a little earlier, I could have gotten her to cuckold me.
Anyway, fast forward to May of my senior year. Now her and I are best friends, and not only that, but I've figured out that I'm officially submissive, that I'm into chastity, T&D, cuckolding (even though I wasnt sure what it was yet and wasnt ready to admit it), and I'm officially ready to be some nice girl's bitch. The first time (kind of) was in May of that year. She had been going out with one guy who used to chill with us, and she didnt tell me that she was officially with him because she knew how I felt, but mostly because he was small and completely scared of me, and especially scared of my other friends. Plus they both had to see me everyday, etc, etc. Anyway, we were hanging out takeing at a friends house, just like 6 of us. After getting pretty takes the two of them went into the bathroom and just stayed there.
I had no idea what was going on, but I could see the way the other girls were acting, and I never expected her to get with this particular guy, so I just had to find out. Now I was kind of takes, so I dont remember everything that happened. But what I do remember is that I hung around in the hall, and whatever I said, I got her to come out twice. I remember her being slightly annoyed, but more amused than anything, and telling me she wasnt doing anything, go away, whatever. It was playful, but it was obvious that whatever she was doing, she didnt wanna hear me bitching while she did it. Now that I think back, the vibe coming from the other girl we were with should have told me something was going on. You have to remember, I didnt know officially that they were dating. Everyone else knew, but I only suspected. So I thought I looked like a takes friend being a pest to everyone else, but its now obvious that I looked like a pathetic cuckold ex boyfriend helplessly calling her from the hall while she had someone else's cock in her mouth.
So we kept takeing, and the night went on. A few hours later, things were slowing down, and I went to go outside.... and as soon as I opened the door, there were the two of them making out. They looked completely shocked. They each said something to me because they knew they had been trying to keep me from finding out, and I just said whatever and went to my car. Anyway, when I first realized what cuckolding was and realized that I absolutely wanted it, what happened that night was one of the first cuckold fantasies I masturbated to for a long time. When she was in the bathroom and I called for her and she came out giggling at me, only to tell me a lie and go back to sucking her lovers cock.
I realized that totally turned me on. Especially the part about her telling me a "lie". I say it that way because when she told me she wasnt doing anything, I realized afterward that she had actually told me EVERYTHING with her tone of voice, eyes, laugh, body language etc. It was one of those lies that she didn't even expect me to believe. When she looked me in the eye and said those words she was really saying "Duh, I'm sucking my boyfriends cock. And I'm liking it. Sparing your feelings is becoming slightly annoying now. I dont care if you listen at the door, cry like a baby, whatever. Just do it quietly." And thats honestly how she felt. If I wasnt so excited between the jealousy and the sexual feelings I hadnt worked out yet, I might have understood her at that moment. She wanted me to know. If I had just known myself a little better I couldve told her what I wanted, and she loved me enough that right now, 6 years later, I would probably still be watching her get fucked by other guys.
Actually, breaking up with her is actually the most important part of the story of my entire sex life. Because we lost out virginity to each other, we had sex ten times, the last time being in January of 2003, we broke up, and I have not had sex with anyone since. It has been over 7 years since I've had sex. After her, one ex gf gave me 3 handjobs, and one super hot girl dry humped me and played with my dick all night, and thats it. I'm taking a while to write the story of my entire sex life because I really want to get it right and figure out alot about myself by doing it.
I mean, alot of people here may claim they havent had sex in 7 years, but its different at a certain age, its different with marriage, its different if you've never had sex. There are alot of factors, and I think my case is extraordinary. I'll let everyone weigh in when I post my story finally. But if anyone wants to talk to me about that particular piece of information about my sex life, feel free to message me.
Now, onto the first time I KNEW that I absolutely wanted to be cuckolded, knowing exactly what it was, and immediately went home and masturbated to it.... This is 2 or 3 months after that first incident, during summer vacation of my senior year. Same ex girlfriend, same friends, getting takes on the weekend. Except this time we were at an older guys house, a guy who went to our school as well. After me and her had broken up, the first permister she fucked was this guy John, an older guy. He was friends with the guy who's house we were at, and he was there that night. We partied all night, and then came the end of the night.
It was daylight and I was just waiting for cops to change shifts so I could drive home down my favorite road. I finish my last beer and go inside and sit down. I look over on the other side of the room, right in front of me like a good show to watch, its her and John. We're all just sitting there, doing nothing, kind of watching tv. And John keeps trying to get into her pants to finger her. She keeps slapping his hand away, and this goes on for almost a half hour right in front of me. She didnt want to do anything in front of me, because she had no idea that I wouldve sat and watched. But if she had known, she wouldve did it without even thinking about it. But I remember it clearly, she wanted to, badly.
Anyway, I remember sitting there, and that was the first time that it hit me.... I wanted to see her get fucked right there. John was the kind of guy who didnt give a fuck, he wouldve told me to enjoy the show if anything. I dont think he even knew we had been together before. I was hoping she would give in and let him go for it. But she didnt. So I looked around and realized that as soon as me and the two people outside were gone, they were gonna fuck right there. Probably as soon as I was gone. I'm pretty sure I was the only reamister. At this time I was the only one there with a car, so just to get her to confirm it for me, I asked her if she wanted a ride home, and she said no. That meant she was gonna get fucked and walk home later.
It was only a 15 minute drive home for me, and all I had to do was drop my pants and hop into bed. So just as I was grabbing my cock, I was %90 sure that her pussy was being filled at that very moment, and it turned me on. Now the incident that happened a few months earlier was the incident that created the first cuckold fantasy I really enjoyed. But this time was the first time that I knew the girl I loved was going to fuck someone before it happened, while I was helpless to stop it, and had to go home and masturbate AS it happened. And most importantly, this was the first time that I know for a fact I was turned on by it. The times before this when I had been close by and knew that she might fuck someone that night, my jealousy would cause me to do things that put me further away from it all, and then I would masturbate to her at home later. But this time it was official... She couldve told me she wanted to fuck this guy in my car, and at that moment I would have given her the keys, opened the door for her, and stood outside holding her purse and her shoes for her, watching my ex gf get fucked by someone else in my own car. So I guess I can say that this was the time where my arousal overtook my jealousy. So yeah, that was definitely the first significant moment.