Straight Male / 26
Love Being Told It’s Small
So I’ll start from where this all began. Back in high school we were at a party with this girl I had talked to on and off all throughout high school. I was a senior in high school and still a virgin and this was the girl I wanted to get with because I thought she was hot af and was definitely a slut. I tried basically all night to get her to hook up with me but by the end of the night it was actually one of my closest friends that fucked her. I didn’t really talk to my friends about the fact I wanted to bang her so it wasn’t like my friend knowingly did anything wrong so I was never mad at him obviously. The next night we were texting about all the details where he told me everything they did including that they fucked on and off for 5 hours that night and they both came 4 times that night, and he then told me where exactly he came each time. He told me the 1st time he just pulled out and finished on her ass, 2nd time he pulled out but she quickly got her mouth around it so he would cum in her mouth and the last 2 times he busted in her because she told him by then she was on the pill. I jerked off to everything he told me for months not even realizing it was my first time being cuckholded.
So fast forward to right after graduation, she finally gives me my chance but doesn’t let me just hit like everyone else got too, we started dating before I got to fuck her. So the night happened when I 1st fucked her and it was completely normal sex, obviously my 1st time and she knew that so of course it probably wasn’t great for her but I thought it was fantastic and was so happy I was no longer a virgin. When we were just laying there after she fell asleep on me and i stayed awake just thinking about it all, that’s when I started to think about my buddies story with her. I immediately thought about the fact the sex had to be so much better for her with my friend because he knew what he was doing with a girl ANNND I knew my friends dick was close to 3 inches bigger then me. We were like really close friends so we had compared our dick size a year or so prior and he had a 7 inch dick on the dot with a little more girth then me but not a ton, my dick is only 4.3 inches. That weirdly turned me on and I jerked off to that thought the next day when she had left. Now don’t get me wrong, I can tell you from experience that you can have amazing sex even with a small dick BUT I also love the idea that I can quite hit as deep inside of a girl or stretch them out as much as others they have been with.
So over the next 2 weeks we were in the early part of the relationship where all you do basically is have sex and slowly and slowly my urges started coming out, I started saying things like “oh you like that little dick?” Or “can you feel it babe?”. She was so nice and always would say it was so big back to me, until one day. It was like 2 pm after she just got to my house and we quickly got into it since we were home alone the rest of that day and I did something to her about it being small and she immediately stopped and looked back at me while me dick is in her and said “why do you always say your dick is small?”. I was shocked even though I shouldn’t have been and just quietly responded “I kinda like to be told I have a small dick.” She looked at me with a stunned confused face and my heart sank thinking I screwed this all up but THEN, a wicked sinister smile came from her and she said “okay we can do that” and then started up again quickly. Best decision I made in my life being honest with her because she clearly loved it, immediately went in telling me how tiny it was as our pace quickened and it went into a completely different world of sex. I became more aggressive as she spent the entire time that she wasn’t moaning or swearing telling me about how small my dick was. It was the 1st time I had made her actually cum during sex. The only time she had before was when I gave her oral. We laid there after I blew my load covering her beautiful ass in cum, each of us breathing heavily before slowly looking at each other and laughing before she said “that was fucking awesome”. She asked me when I realized that I liked that and I told her everything I told you all, starting from her hooking up with my friend but not including that I jerked off too it. She thought it was awesome but also funny and then noticed I was hard again so we went for round 2.
During round 2 I mentioned my friends name a couple times which she never responded too and then when we were laying there after she was super quite. I asked what was wrong and she started to cry to which I was confused as hell by but then she finally spoke and said she was mad at herself for hooking up with my friend because she said she knew how this would go and that I would hate her for hooking up with him, but before I let her go on and cry more I interrupted her with a “woah woah woah, never forgive you? Dude I think it’s hot as fuck that you fucked my friend”. Her tears stopped as she hit me with the same shocked look as before and asked if I was serious. I told her yes and also mentioned again that I knew he was bigger then me and that you probably liked it more. Her same wicked in disbelief smile came back as the possibilities clearly ran wild in her head. My dick was hard again so I got on top of her and grabbed her throat and slid mud dick inside her then looked at her Evil smiling face and said “why don’t you tell me about how the sex with him was”. The sex from there on out was insanely good. I remember like a week later she told me this has been some of the best sex she had ever had in her life, I told her to just imagine how good it would be if my cock wasn’t small which she quickly cut me off and said my cock being small and me loving being told that was what made it so good. She said every guy is the same wanting to be told they have this big monster dick even when they have a small dick and don’t know what they’re doing with it or if they do have a big dick most of the time they just painfully pound her pussy until they finish and still feel the need to be told there massive cock is big. She said it was so refreshing to not have to lie to a guy so they can feel better about there tiny dick or not mention that she had been with bigger guys that can do certain things better in bed especially the fact that she had one of my closest friends fuck her brains out and she can just talk about it and relive other good sex she has had. I laughed the whole time she went on and on and then finally added “not only do I not care about you talking about other sex but I think it would be hot as fuck if you got fucked my other guys while we dated”. Silence followed that statement so I looked over to her, yet again her shocked face returned but the smile was already on her face. “You would actually let me fuck other guys?” I laughed and said yes, I would even watch you get fucked. She looked like a kid on Christmas morning. She asked if she could fuck my friend again or just random people, I told her I’d mainly prefer it be random people so I didn’t have to have awkward conversations with all my friends but that I really wanted her to fuck my the one she already had again. She had admitted already my buddy was the best hookup she ever had and one of the few that could fuck her much better then I could so she was all in on that being her 1st hookup. I texted my buddy about it telling him it was okay and asking him to keep it a secret and he was all in. Just then he texted my girlfriend got a text from him saying to get to his house now with a picture of his dick. She looked to me for permission to which I laughed and nodded. She through her sexy lingerie on and ran out of the house basically. I texted my buddy saying take good care of her and it was up to him but I’d love a video during and then if you could cum on her her face and send me a pic that would be awesome. He said definitely and then I waited.
After about 30 minutes I got a 30 second video of her sucking his massive dick and looking into the camera with her sick smile. About 20 minutes later I got another video, this was of her ass bouncing in doggy on his dick while she was nearly screaming how much bigger it was then me. (I found out later she only knew about the blowjob video and the facial picture so I showed it to her and she thought it was hilarious). About 15 minutes after that video I got one of my favorite pictures ever which is of my beautiful girlfriend on her knees holding my closest friends big dick in her hand with mascara and cum dripping down her face and her beautiful big smile. She ended up staying the night at his place so they could bang all night and returned in the morning to tell me the details. This was the start of my cuckhold life with the girl of my dreams which has been amazing. She is so thankful for me allowing her to have other dudes fuck her she has surprised me so many times with letting me fuck her smoking hot friends and have awesome 3 ways with her friends and other guys. I actually decided to write this because last weekend my wife had a dream come true where she had a train of 10 guys fuck her while I watched. If there is a lesson to take from this it’s too just be open with your fetishes and kinks because everyone has them and it can lead to awesome adventures.
So fast forward to right after graduation, she finally gives me my chance but doesn’t let me just hit like everyone else got too, we started dating before I got to fuck her. So the night happened when I 1st fucked her and it was completely normal sex, obviously my 1st time and she knew that so of course it probably wasn’t great for her but I thought it was fantastic and was so happy I was no longer a virgin. When we were just laying there after she fell asleep on me and i stayed awake just thinking about it all, that’s when I started to think about my buddies story with her. I immediately thought about the fact the sex had to be so much better for her with my friend because he knew what he was doing with a girl ANNND I knew my friends dick was close to 3 inches bigger then me. We were like really close friends so we had compared our dick size a year or so prior and he had a 7 inch dick on the dot with a little more girth then me but not a ton, my dick is only 4.3 inches. That weirdly turned me on and I jerked off to that thought the next day when she had left. Now don’t get me wrong, I can tell you from experience that you can have amazing sex even with a small dick BUT I also love the idea that I can quite hit as deep inside of a girl or stretch them out as much as others they have been with.
So over the next 2 weeks we were in the early part of the relationship where all you do basically is have sex and slowly and slowly my urges started coming out, I started saying things like “oh you like that little dick?” Or “can you feel it babe?”. She was so nice and always would say it was so big back to me, until one day. It was like 2 pm after she just got to my house and we quickly got into it since we were home alone the rest of that day and I did something to her about it being small and she immediately stopped and looked back at me while me dick is in her and said “why do you always say your dick is small?”. I was shocked even though I shouldn’t have been and just quietly responded “I kinda like to be told I have a small dick.” She looked at me with a stunned confused face and my heart sank thinking I screwed this all up but THEN, a wicked sinister smile came from her and she said “okay we can do that” and then started up again quickly. Best decision I made in my life being honest with her because she clearly loved it, immediately went in telling me how tiny it was as our pace quickened and it went into a completely different world of sex. I became more aggressive as she spent the entire time that she wasn’t moaning or swearing telling me about how small my dick was. It was the 1st time I had made her actually cum during sex. The only time she had before was when I gave her oral. We laid there after I blew my load covering her beautiful ass in cum, each of us breathing heavily before slowly looking at each other and laughing before she said “that was fucking awesome”. She asked me when I realized that I liked that and I told her everything I told you all, starting from her hooking up with my friend but not including that I jerked off too it. She thought it was awesome but also funny and then noticed I was hard again so we went for round 2.
During round 2 I mentioned my friends name a couple times which she never responded too and then when we were laying there after she was super quite. I asked what was wrong and she started to cry to which I was confused as hell by but then she finally spoke and said she was mad at herself for hooking up with my friend because she said she knew how this would go and that I would hate her for hooking up with him, but before I let her go on and cry more I interrupted her with a “woah woah woah, never forgive you? Dude I think it’s hot as fuck that you fucked my friend”. Her tears stopped as she hit me with the same shocked look as before and asked if I was serious. I told her yes and also mentioned again that I knew he was bigger then me and that you probably liked it more. Her same wicked in disbelief smile came back as the possibilities clearly ran wild in her head. My dick was hard again so I got on top of her and grabbed her throat and slid mud dick inside her then looked at her Evil smiling face and said “why don’t you tell me about how the sex with him was”. The sex from there on out was insanely good. I remember like a week later she told me this has been some of the best sex she had ever had in her life, I told her to just imagine how good it would be if my cock wasn’t small which she quickly cut me off and said my cock being small and me loving being told that was what made it so good. She said every guy is the same wanting to be told they have this big monster dick even when they have a small dick and don’t know what they’re doing with it or if they do have a big dick most of the time they just painfully pound her pussy until they finish and still feel the need to be told there massive cock is big. She said it was so refreshing to not have to lie to a guy so they can feel better about there tiny dick or not mention that she had been with bigger guys that can do certain things better in bed especially the fact that she had one of my closest friends fuck her brains out and she can just talk about it and relive other good sex she has had. I laughed the whole time she went on and on and then finally added “not only do I not care about you talking about other sex but I think it would be hot as fuck if you got fucked my other guys while we dated”. Silence followed that statement so I looked over to her, yet again her shocked face returned but the smile was already on her face. “You would actually let me fuck other guys?” I laughed and said yes, I would even watch you get fucked. She looked like a kid on Christmas morning. She asked if she could fuck my friend again or just random people, I told her I’d mainly prefer it be random people so I didn’t have to have awkward conversations with all my friends but that I really wanted her to fuck my the one she already had again. She had admitted already my buddy was the best hookup she ever had and one of the few that could fuck her much better then I could so she was all in on that being her 1st hookup. I texted my buddy about it telling him it was okay and asking him to keep it a secret and he was all in. Just then he texted my girlfriend got a text from him saying to get to his house now with a picture of his dick. She looked to me for permission to which I laughed and nodded. She through her sexy lingerie on and ran out of the house basically. I texted my buddy saying take good care of her and it was up to him but I’d love a video during and then if you could cum on her her face and send me a pic that would be awesome. He said definitely and then I waited.
After about 30 minutes I got a 30 second video of her sucking his massive dick and looking into the camera with her sick smile. About 20 minutes later I got another video, this was of her ass bouncing in doggy on his dick while she was nearly screaming how much bigger it was then me. (I found out later she only knew about the blowjob video and the facial picture so I showed it to her and she thought it was hilarious). About 15 minutes after that video I got one of my favorite pictures ever which is of my beautiful girlfriend on her knees holding my closest friends big dick in her hand with mascara and cum dripping down her face and her beautiful big smile. She ended up staying the night at his place so they could bang all night and returned in the morning to tell me the details. This was the start of my cuckhold life with the girl of my dreams which has been amazing. She is so thankful for me allowing her to have other dudes fuck her she has surprised me so many times with letting me fuck her smoking hot friends and have awesome 3 ways with her friends and other guys. I actually decided to write this because last weekend my wife had a dream come true where she had a train of 10 guys fuck her while I watched. If there is a lesson to take from this it’s too just be open with your fetishes and kinks because everyone has them and it can lead to awesome adventures.
