So this post is about a couple months or so in the making. Forgive any tangents or ramblings, this might be a long read, but I promise it'll be worth it.
My gf of 2 years has always been the jealous type. Any time I would mention interacting with another girl she didn't know, she'd try to play it off like she was fake mad and say something like "what girl? did she hit on you??" I'd of course say no to which she'd say something along the lines of, "you're damn right." I of course didn't want to have to deal with an angry jealous girlfriend so I never brought up my ex's to her and things that I've done in my sexual history or even look in a hot girl's direction when we were together.
I don't want to paint her in a negative manner with that alone so let me just describe her to you. She's really nice and genuine aside from that side of her and goes of her way to make me happy whenever she can. She can be a bunny rabbit - so much energy - and LOVES sucking my cock (and balls too!). We've done anal once before, but she didn't seem as into it as I'd hoped. In all, up to this point in my story, she was definitely great in the sack, but nothing to share cuckolding-wise ;)... yet...
Fast forward to a couple months ago when I was watching an episode of Boardwalk Empire - the one where Mr Purnsley is hit on by a white woman and brought back to her apartment for a fuck session. The two are interrupted by the woman's, also white, husband who tells them to keep fucking while he gets off to it. Long story short the scene ends horrifically, but that might've been the first time I even thought of the idea of cuckolding or wife sharing (and not any sort of violence or murder, in case that wasn't clear lol). That curiosity led me to cuckold porn and ultimately this blog which I now visit weekly. So having read a number of posts, seen pictures, and even watched some videos of some couples and friends having fun together, I started to like the idea... A lot...
Not too long after, we bought my girlfriend her first dildo at my insistence. She admitted that she was curious about getting one but was afraid that I'd somehow be upset with her playing with herself without me. I told her that I wanted to watch and that I liked seeing her having a good time. A few nights later while we're having our own fuck time, I ask her to take her dildo out and suck on it while I'm inside her. I whisper into her ear if she likes playing with 2 dicks at once. She moans yes and says that she wishes there were 2 of me so that she could suck my dick and get fucked by me at the same time. 'Bingo', I think. 'This is my way in.' I make her suck on it some more and I eventually cum inside her tight little pussy just as she's cumming too. That was hot for dipping our toes in a little (metaphorically, lol. I didn't put my toes in her).
A few nights later, we're at it again, and again, I ask her if she likes the thought of having 2 cocks in her holes. She lustfully gives me the affirmative and her pussy seems to drip even more than it usually does. Then one night as we're in the middle of a hot ride, I'm fucking her from behind, smacking her ass harder and harder. Her ass is so red and you can see exactly where my hands have been punishing this naughty girl. In the heat of the moment, I lean close to her ear and ask her if I can tell her something nasty. She replies "fuck yes". "Sometimes, I think about you taking dick from 2 different guys." "You do?" she responds in astonishment. "That's so bad! But... you wouldn't be mad?" "No," I tell her. "I think it'd be hot seeing you turn another guy on, get his dick hard, and pleasure him til he cums." She moans as I keep fucking her tight, slippery cunt. I pound her harder and harder, and finally she cums all over my dick. Gasping between orgasmic moans, she utters "cum inside me!". She finally falls over in exhaustion after I unload a massive amount of cum inside her pussy.
Usually when we have sex and talk dirty, we don't say much about it afterwards or any time we're NOT having sexy time. But a day later, I flat out tell her, in a most sheepish tone, "honey... I really do think that it's fucking hot imagining you with other guys..." She couldn't believe her ears, but I can tell she was pleasantly surprised by my confession. "You do?!" "Yeah. Like if we had another guy with us, and he fucked you while you sucked my cock." She still can't believe it, but I know her heart is racing with excitement. "Wow...I.... Who would we even ask?" 'Whoa' I think. 'She immediately jumped to who we would ask instead of keeping it as just thoughts.' Before, I think I would have been pretty mad at this, but it started turning me on more.
She's already excited, thinking about who she could fuck! I like this. "I dunno," I say. "It'd have to be someone we trust and know at least a little bit." "Yeah, at least for the first time." Her ears perk up at this mention of "the first time". "What about [Kris]?" I ask.
('Kris', lets call him, is my housemate and one of my closest friends. One drunken night, he blurted out to me that he really wanted to fuck my girlfriend. I was too shocked and drunk myself to be upset about it, and had just brushed it off). "Maybe," she quietly says "but won't it be weird since we're all friends?" "That's true... but it might be okay since we all trust each other." "What about your boss [Nick]?" My girlfriend knows 'Nick' and I'm pretty cool with him myself. He's only a little bit older than me, super nice guy, and I can tell that lots of girls think he's hot. "Oh, I might be okay with that..." I respond.
So over the next 2 weeks we just kind of go back and forth with who we think might be cool with this fantasy. I'm leaning more towards my housemate 'Kris' since I trust him the most, and because of that, I start showing him video and pictures of my girlfriend playing with herself and sucking me off. He wasn't at all weirded out and actually really liked it.
He even complimented my girlfriend's clean pussy. I was getting turned on by his obvious attraction to her naked body. I'll mention here that my girlfriend and I don't live too close from each other - about a 5 hour drive, so we don't see each other every day, or even every weekend for that matter. During this time of fantasizing about her with other men, I begin asking her things like "what if I told you to give a guy a handjob in a club this weekend?" or "what if you started talking to the guys at the gym who hit on you and bring them to your place to fuck?".
She loved every scenario I gave. "I love that you're so bad!" she said. "I'll do anything you tell me to. You're the boss. You know, I'm more nasty than you think I am..." "Oh? You are?" I ask. "Yeah. Like, I think it'd be really hot to be tied up and have you and another guy just have your way with me. Fuck me in all my holes. Then cum on my body...." 'Hoooolllyyyy fuck....' my head is about to explode ;) "I've also fantasized about just fucking a random group of guys. White dicks, blacks dicks, any kind. Just fucking me in public and cumming on me. Just me soaked in their hot cum..." I... seemed to have unleashed a beast!! Wow. I still can't believe she said those things, but I fucking love it! (and I bet you all are loving hearing of it too!)
Now is the time where the story catches up to present day. She's going to be visiting me this weekend and I've asked if she wants to actually try doing something crazy. She said yes and that I should ask 'Kris'. The other day I had a few drinks with him to get him relaxed and told him of this fantasy of ours. He was a really cool and understanding dude in that he said he definitely wants to but wants to make sure we're both realllyyy okay with it and that he is too since this has the potential to ruin our friendships. I thanked him for his honesty and told him that he's welcome to join us in my bedroom if he so desires. After talking some more, my girlfriend and I decided that he could watch her play with herself and that we'd take things one step at a time from there. We don't want to rush it so this weekend will be a test.
If anything more happens, I'll follow up. Thanks for reading.
A & P