If you read my first post about becoming a cuckold, you read about how when she was still a senior in high school, we actually swapped partners with a close girlfriend of hers. You also saw how the other guy one-upped me and fucked the shit out of her, right in front of me, while I struggled to keep my dick hard, while unsucessfully trying to play "pretend stud" with his girlfriend, and how that didn't work, and in the end, I embarassed myself further by cumming within 30 seconds of getting in her pussy after the other couple left, and Kim had told me to "last longer like the other guy".
After that, we cooled it completely(keep in mind for high school, this was pretty far out anyways!). Kim acted like she wasn't constantly thinking about other guys, but I knew different.
We then entered an unusual period for about a year, where we "pretended" that Kim wasn't thinking about other guys, and I wasn't overt in accusing her, role playing, or setting her up for "interesting situations", but I was.
First of all, my best friend Chris. He was a ladies' man, he had a string of girlfriends, that wouldn't last, he was just basically "chasing tail", and getting alot of it(at this point we were both 21, so he started hitting bars, and finding some luck). One time, Kim set up her friend with Chris, and we did a big double-date to Disneyland. The whole time, I would consciously look for flirtation with Kim and Chris(even though there was a girl for Chris), and sure enough, it was the "little things" I noticed, like excessive eye contact, standing too close, etc., I noticed that every time we sat together, Kim would be on one side of Chris, the other girl on the other side, and me off to the far side of Kim(and of course, the conversations were all based on those two, even Chris's date seemed marginalized!).
Later that night, we went back to Chris's house(he lived at home but they had a "granny shack" for Chris in the back), soon the four of us were making out on the couch(seperate ends). Kim shocked me by pulling her panties off from under her skirt, while Chris watched. Soon Chris took the other girl into the bedroom, but I noticed he didn't shut the door all the way. Soon Kim was forcefully making out with me like she had never done, getting really vocal, telling me how wet she was, and how she needed fucking really bad! Kim was soon naked, taking off her clothes before I could even do it for her! She was practially SHAKING she was so horny! Pretty soon we could hear moans and squeaking bedsprings in the other room, Chris was obviously showing her a good time. By now, Kim was making me lick her pussy, and then pulled me up and slipped my hard dick into her pussy. Believe it or not, I lasted quite a while, probably 5 full minutes, but eventually, I couldn't help it, the combined moans(kim was way too loud at this point)proved too much, and I came inside Kim. Kim didn't miss a beat, and jumped on top of me, where she proceeded to have a super-intense, and super-loud orgasm! When we settled down, we could still hear Chris and Kim's friend in the other room. I decided to play devils' advocate, so I snuck up to the crack in the door and peered in: it was pretty dark in the room, but looking in, I could clearly see Chris's ass, going up and down like a machine, in between the girl's thighs, she was moaning repetitively, like she was in a trance, Kim surprised me, by coming up to the doorway too, and looking in with me. She whispered into my ear "Chris really knows how to fuck, huh?". We snuck back the couch and waited. It took about 40 minutes until Chris and the girl came out. Chris commented on how loud Kim was, and Kim responed "I guess it was the inspiration coming from your room that caused that, I hope I didn't distract you guys!".
I took Kim home, and we didn't really talk about what that was like having sex in almost the same room with Chris, but Kim was horny as hell for the next few days, and I couldn't help but notice that she brought up Chris's name quite often.
A few weeks later was Prom. Chris had the same girl as his date, so of course we went double. At one point in the night at the dance, Kim and I were standing, having drinks. Chris walks up, with his cool demeanor, and confidently asks Kim to dance. I'll never forget the humilation of them both instantly handing me thier drinks, and Chris taking Kim's hand, and slowly leading her onto the dance floor. Chris and Kim danced for like 10-20 minutes....forever......finally Kim came back and said offhandedly "that was awesome, Chris is a great dancer!". She was gushing. Later that night, we went back to our motel alone. Kim wanted to stay and party with the group(about 3 couples including Chris and his date reserved a room together, I was smart enough to realize we would have a better chance at having sex if we were in our own room), Chris was fighting with his date, so he poured his attention on her(right in front of me, but nothing overt), they would stand really close talking, I would notice the subtle flirting like the way she would touch his arm, or chest, and the constant eye contact. Needless to say, I was super-horny, so I convinced her to go back to our room. Once in the room, Kim was out of her prom dress(just like the joke), and soon enough, she was instructing me to eat her out. She then said that she wanted me to keep licking, and that she wanted to make sure she came first, so she matrubated while I ate her out for like 10 minutes or so. Finally, she came, loud, all over my face, and her fingers. The whole time, I couldn't help but imagining what was going on in her head. Finally, she let me slide my dick in, I couldn't help it, I said "I know you wish Chris was here to fuck you!". Kim didn't skip a beat, and replied "Just like I wish you could fuck me like Chris!". There. It was out in the open. I began thrusting in and out of her like a madman, and I said "I'm sure he will fuck you one of these days". Kim then teased me and said something like "Go ahead and try and fuck like Chris!". At that point, I lost it, and came and came and came inside my girlfriend. Kim then rolled over onto her stomach, and used her fingers to mastrubate once more, this time though, I kneeled over her stroking my now soft dick and said "Go ahead and cum thinking about him, it's ok, I understand". Kim then began to moan his name into the pillow, while she frantically fingered herself to another orgasm.
We went to sleep soon after, and things were a little wierd the next few days, neither of us talked much about what had happened. I think Kim was ashamed of herself for being such a bad, sluttly girlfriend.
I will continue to post further stories about our long road to cuckoldry. It's all true, and it goes on over 20 years, and it keeps getting better, these are the "old days" stories, things get way more steamier.
I appreciate comments and replies, and questions. I love the way custerslaststand takes apart threads and makes comments on them. Feel free to let me know how pathetic it is for me to have my best friend make my girlfirend cum more than I can!
OnePumpnDump
After that, we cooled it completely(keep in mind for high school, this was pretty far out anyways!). Kim acted like she wasn't constantly thinking about other guys, but I knew different.
We then entered an unusual period for about a year, where we "pretended" that Kim wasn't thinking about other guys, and I wasn't overt in accusing her, role playing, or setting her up for "interesting situations", but I was.
First of all, my best friend Chris. He was a ladies' man, he had a string of girlfriends, that wouldn't last, he was just basically "chasing tail", and getting alot of it(at this point we were both 21, so he started hitting bars, and finding some luck). One time, Kim set up her friend with Chris, and we did a big double-date to Disneyland. The whole time, I would consciously look for flirtation with Kim and Chris(even though there was a girl for Chris), and sure enough, it was the "little things" I noticed, like excessive eye contact, standing too close, etc., I noticed that every time we sat together, Kim would be on one side of Chris, the other girl on the other side, and me off to the far side of Kim(and of course, the conversations were all based on those two, even Chris's date seemed marginalized!).
Later that night, we went back to Chris's house(he lived at home but they had a "granny shack" for Chris in the back), soon the four of us were making out on the couch(seperate ends). Kim shocked me by pulling her panties off from under her skirt, while Chris watched. Soon Chris took the other girl into the bedroom, but I noticed he didn't shut the door all the way. Soon Kim was forcefully making out with me like she had never done, getting really vocal, telling me how wet she was, and how she needed fucking really bad! Kim was soon naked, taking off her clothes before I could even do it for her! She was practially SHAKING she was so horny! Pretty soon we could hear moans and squeaking bedsprings in the other room, Chris was obviously showing her a good time. By now, Kim was making me lick her pussy, and then pulled me up and slipped my hard dick into her pussy. Believe it or not, I lasted quite a while, probably 5 full minutes, but eventually, I couldn't help it, the combined moans(kim was way too loud at this point)proved too much, and I came inside Kim. Kim didn't miss a beat, and jumped on top of me, where she proceeded to have a super-intense, and super-loud orgasm! When we settled down, we could still hear Chris and Kim's friend in the other room. I decided to play devils' advocate, so I snuck up to the crack in the door and peered in: it was pretty dark in the room, but looking in, I could clearly see Chris's ass, going up and down like a machine, in between the girl's thighs, she was moaning repetitively, like she was in a trance, Kim surprised me, by coming up to the doorway too, and looking in with me. She whispered into my ear "Chris really knows how to fuck, huh?". We snuck back the couch and waited. It took about 40 minutes until Chris and the girl came out. Chris commented on how loud Kim was, and Kim responed "I guess it was the inspiration coming from your room that caused that, I hope I didn't distract you guys!".
I took Kim home, and we didn't really talk about what that was like having sex in almost the same room with Chris, but Kim was horny as hell for the next few days, and I couldn't help but notice that she brought up Chris's name quite often.
A few weeks later was Prom. Chris had the same girl as his date, so of course we went double. At one point in the night at the dance, Kim and I were standing, having drinks. Chris walks up, with his cool demeanor, and confidently asks Kim to dance. I'll never forget the humilation of them both instantly handing me thier drinks, and Chris taking Kim's hand, and slowly leading her onto the dance floor. Chris and Kim danced for like 10-20 minutes....forever......finally Kim came back and said offhandedly "that was awesome, Chris is a great dancer!". She was gushing. Later that night, we went back to our motel alone. Kim wanted to stay and party with the group(about 3 couples including Chris and his date reserved a room together, I was smart enough to realize we would have a better chance at having sex if we were in our own room), Chris was fighting with his date, so he poured his attention on her(right in front of me, but nothing overt), they would stand really close talking, I would notice the subtle flirting like the way she would touch his arm, or chest, and the constant eye contact. Needless to say, I was super-horny, so I convinced her to go back to our room. Once in the room, Kim was out of her prom dress(just like the joke), and soon enough, she was instructing me to eat her out. She then said that she wanted me to keep licking, and that she wanted to make sure she came first, so she matrubated while I ate her out for like 10 minutes or so. Finally, she came, loud, all over my face, and her fingers. The whole time, I couldn't help but imagining what was going on in her head. Finally, she let me slide my dick in, I couldn't help it, I said "I know you wish Chris was here to fuck you!". Kim didn't skip a beat, and replied "Just like I wish you could fuck me like Chris!". There. It was out in the open. I began thrusting in and out of her like a madman, and I said "I'm sure he will fuck you one of these days". Kim then teased me and said something like "Go ahead and try and fuck like Chris!". At that point, I lost it, and came and came and came inside my girlfriend. Kim then rolled over onto her stomach, and used her fingers to mastrubate once more, this time though, I kneeled over her stroking my now soft dick and said "Go ahead and cum thinking about him, it's ok, I understand". Kim then began to moan his name into the pillow, while she frantically fingered herself to another orgasm.
We went to sleep soon after, and things were a little wierd the next few days, neither of us talked much about what had happened. I think Kim was ashamed of herself for being such a bad, sluttly girlfriend.
I will continue to post further stories about our long road to cuckoldry. It's all true, and it goes on over 20 years, and it keeps getting better, these are the "old days" stories, things get way more steamier.
I appreciate comments and replies, and questions. I love the way custerslaststand takes apart threads and makes comments on them. Feel free to let me know how pathetic it is for me to have my best friend make my girlfirend cum more than I can!
OnePumpnDump
