I posted this once before, over a year ago. But deleted it because I got nervous and didn't want anybody in my real life knowing my kinks if they found this lol.
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Be warned, these stories are all 100% true, however…. There is no actual cheating/cuckolding in these stories.
I wanna start with my ex-girlfriend of 5 years that I dated from the end of high school through a good portion of college (all of college for her, not for me since she was a year older and had a major that took a year less than mine).
We'll call her Liz (very made up name). I knew I had a cuckold fetish and liked being teased about the size of my penis, but I had never told anybody this at the time.
Liz and I went to a halloween party my freshman year of college. And we got back to my house and in the night and were both pretty drunk and having sex. I forget what prompted it, but I got the courage to ask her if she'd want to get fucked by another guy. She was extremely taken aback, but not alarmed. Like, genuinely surprised. She was asking if I was serious, and me being drunk, I was very adamant that I was. I asked her what the odds were that she would do it. I'll never forget this (because the number was so specific lol), she goes "like 77%"
Later, she told me she liked the idea but wasn't sure if she could ever actually do it. She began to tease me a lot. "I bet you'd like it if I was fucking another guy right now," while we were having sex and things like that.
She also knew I wanted it to be with a guy whose penis was bigger than mine. So she would tease me a lot about that too. And one night while she was giving me head and teasing me, I decided to playfully fight back a little bit. After she called me small, I laughed and said "the biggest you've ever had." (side note I forgot to mention, I lost my virginity to her. She had had sex with 1 boyfriend prior to me)
After I said this, she smirks and gets real snarky. Like, almost confident/arrogant in that moment. I just said, "what?" She took my penis out of her mouth and said, "you don't want me to say anything to that."
I'm like, "tell me." She says, "No, you don't actually want to know." I reassured her that I did. She then, for the first time, reveals "(ex-BF) was a lot bigger." My heart started pounding and I kept asking her if she was serious. I asked her to show me about how big he was compared to mine. She basically took my penis and made a circle with her hand around my circumference, but significantly larger than my girth. And showed me her estimate of his length by holding her hand probably about 3 inches above the tip of mine. For what it's worth, I was actually friends with this guy and played guitar with him before he and her had ever dated lol. He's tall and large. Think of a young country-boy type. So I actually do believe her on his size. And the fact that she didn't actually want to tell me his size because she thought reality would be too harsh for my fantasies.
Most of the teasing with Liz was pretty simple, basic stuff. She never really got close to actually cuckolding me. It was really just a lot of her calling my dick small lol. Last thing I'll say, is after we broke up, we were having 1 final argument about 6 months later because she was drunk texting me while out with her friend. She said, "have fun watching your new girlfriend get fucked by other guys. We all know that's what you want." Lol, fun times.
Next one I wanna talk about, I'll call Eve. This was a couple years later in college. This is also the only girl whose virginity I've ever taken. At this time, I was 22 I believe and Eve was 20.
We were casually dating, and having sex after she had told me she was ready and wanted to lose her virginity. We agreed to be friends with benefits. And I had told her how I thought it would be hot if she had sex with other guys. (Naturally, I also mentioned it'd be hot if they were bigger than me lol).
Eve then texts me one night asking if I thought a friend of mine (he was also one of my roommates at this time) would wanna be friends with benefits with him. She had also told me she was checking out his cock in his basketball shorts when he was doing laundry one day when she was over. Lol, obviously, this could have been very hot if I had encouraged it. She'd just told me she wanted my friend with a bigger cock to fuck her. But to be honest, I pussied out and told her it would make me uncomfortable. (I'm lame, I know). She also later offered (to me only lol) to have a threesome with me and him. But again, I pussied out. She was excited by the idea of a threesome because (in her words) she "might finally get to cum."
Later, Eve and I broke it off, but resumed hooking up the following year. Well at the time, she also had a house of about 3 or 4 roommates. (Same situation I was in, just reversed genders lol). One of her roommates has some sort of health/biology/whatever class and was doing her homework. Eve texts me about how they'd seen an uncircumsized penis in her book and how weird it looked. I'm like, "I'm uncircumsized." She texts back something like, "What?! Your penis doesn't look like that." I told her, it's because she's only seen me hard really so the skin is pulled back and the essentially look the same when hard. I offered to show her and her friends lol.
So after a very long period of waiting for my dick to soften because I was about to send a house full of college girls my soft little penis, I took a picture holding a pencil next to it for scale and sent it to them.
Nothing too exciting happened after that. She basically just told me they thought it was interesting. (Pretty sure these 4 or 5 women in their early 20s had no idea what circumcision was until that night lol, crazy). However, Eve later told me her friends called it "weird and small."
Later on, after Eve had been with a total of 3 guys (2 plus me), she told me I had the smallest penis of the 3. She also told me that one in particular that was the 2nd biggest fucked her really well. She said he "does things with his hips that I don't."
Lastly, I have another ex-girlfriend that I'll call Maggie. Our relationship start as just a series of hookups after college, that slowly became more serious. So I had told her in one of our first hookups that I liked being teased about being small. So one night early on, she asked me if I wanted her to tease me. I'm like, "you can try." She hesistates, and after a few seconds of touching my penis, she says, "you know, it's true what they say about black guys." This obviously began a whole lot of teasing and talk of cuckolding.
Maggie was actually 100% down to do it. She even asked me if she could message a guy from her high school who she had wanted to fuck. He had also wanted to fuck her and she knew that, she said they just never had the timing right. So after a short back and forth with like a "hey what's up" type of message, she said "so you still DTF?" He was lol. They exchanged pictures and sexted. She told him after he sent the picture of his cock "bigger than my boyfriend's so we're all good." Lol it's crazy how casual she was about it.
Maggie actually had plans to fuck him one specific Friday afternoon. He didn't want me there to watch, but I told her it was fine as long as she came over to my house right after.
During the leadup, we were discussing it and I asked what they were gonna do exactly for this date/hookup. She said they were just "gonna go out to a bar and have a few drinks then go back to his place." I asked her if she thought his roommates knew about her if the fact that she has a boyfriend. She said, "I'm sure he's told them. And if not, they'll probably hear me so they're gonna find out. But it's not like we're gonna hang out with them. We'll just say hi to them when we get back to his place then we're probably going to his bedroom."
I said, "PROBABLY going to his bedroom? What would be the alternative?" She goes, "then I guess we'd probably just fuck on the couch in front of them."
Her response was the greatest thing I've ever heard in my life. Especially because her demeanor was so serious. So matter-of-fact. Like, she wasn't saying it as a joke or to tease. She just said it like you would say "yeah I think it's gonna rain today." That was hot lol.
Long story short, he had to cancel. A couple times actually and she got fed up and stopped messaging him.
That's about it. Just wanted to share some fun stories I've had with Cuckolding/SPH teasing. There's been a few other small stories over the years, but these are my favorites to share.
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