This happened a few years ago, and at the time, although it was a hug fantasy of mine, my gf, Kayla, wanted nothing to do with it. We were high school sweethearts, and had been together since then. I was her first and only sexual partner, and other than making out with one of our friends on prom night after being drunk for the first time, she had never done anything with anyone else. Our dirty talk never included anyone else, as every time I brought it up, Kayla would shoot it down, and steer the conversation somewhere else. This went on for quite some time, until I stopped bringing it up. I guess it was just never meant to be.
So imagine to my surprise, when one day out of the blue, Kayla texts me while I’m at work. “Hey, do you still think about sharing me with someone else?”. Taken by surprise it takes me a while to figure out a reply, and in the end I go with “sometimes, yea, why?”. She’s quick to send back “I’ve been thinking about it a little more lately, and the idea of having two guys focusing on me, kind of makes me excited”. Sitting at work stunned “uh, did you have someone in mind?”. Again, taking no time to reply, “It might be fun to try it with Andrew, he’s nice.” Jesus, she’s already got someone in mind??? I guess I took too long to reply, because another message came through quickly, “I mean, he’s your friend, and if I was going to be doing something like this, I want it to be with someone we trust, not some stranger.” She’s clearly thought a lot about this, even down to picking the guy. “How do we know if he would be willing to try this Kayla? I haven’t ever really had this kind of conversation with him you know…”. Again, clearly excited about the possibility, she responds immediately, “You just have to ask him silly. Worst he says is no, but I don’t know why he would 😉 “. I can’t argue with her logic, even if I get the feeling of having a pit in my stomach. I simply reply with “okay”.
After finding some courage to actually type out my first text to Andrew, I sit there going through all the “what if’s”. Hitting send, now I wait. “Hey man… I’ve got kind of a weird question, and I’m not really sure how to ask it, but Kayla and I have been talking, and she wants to have a threesome, and she doesn’t think she would be comfortable with adding anyone else but you.” There, it’s done, I’ve sent it. I put my phone in my desk, and go upstairs at work to grab a coffee, trying to distract myself from how nervous I feel. I just asked my best friend if he would be okay with sharing my gf of 8 years with me. Would he be okay with it? Would he freak out and stop messaging me? God, I couldn’t sit still, I couldn’t concentrate, I had no idea how he would react and it was driving me nuts. I had to see if he texted back, so I took my coffee back downstairs, sat at my desk, trying to look as normal as I can be, and I pulled out my phone. Sure enough Andrew texted back “oh wow man, you guys serious? I love a good 3some, when and where?”. Well fuck, he’s clearly into it, I took a screenshot and sent it to Kayla, and she immediately texts back with a “Yay! I’m so excited he said yes!” For some reason I always thought this would have been a lot more difficult to arrange, and it here it is, only about 2 hours later, everyone seems to be on board. I go back and forth with both of them, and we iron out plans to try this at his place, next Friday. The night I get home, and the minute I walk through the door, Kayla comes from our bedroom completely naked, and simply beckons me with her finger, then turns around and walks back into our bedroom. I drop my bag, take off my shoes, and rush to the bedroom, only to find her lying on her back, legs spread, with both hands above her head.
- Side note – Kayla is 5’6”, 115lbs, with long toned legs, a perfectly flat stomach, and A-cups with just the most perfect little eraser tip nipples. She’s got long dirty blond hair, and wonderful vulva with big labia, but the grip they provide, it’s absolutely incredible.
Needless to say, we end up fucking all over the house for the next week. I feel like a teenager again, and when the mood strikes, we literally go at it anywhere in the house. I can’t remember having this much sex ever. We decided on Thursday morning, we would hold off, as we wanted to have some energy, and be ready to go for what ever happened on Friday night. Kayla was clearly excited as we got ready to go out, and she took her time getting ready in the shower, telling me I had to wait upstairs for her, as it would be a surprise. We called that she was ready to go, and I headed downstairs to put on my shoes. Meeting her down there, she was wearing a nice sweater and a reserved looking flowing skirt, and as I thought this was an interesting choice, I told her she looked beautiful, and off we went. It took us about 25 minutes to get to Andrew’s house, and we didn’t say 1 word until we pulled into the driveway of his place. She did however hold my hand tightly the entire time, clearly a little nervous as to what was going to happen. Before getting out of the truck, she looked over to me and simply asked “ready?”. I answered “I think so”. She smiled, gave me a quick kiss, and got out. Walking together we got to his door, and even before knocking, he yelled out “come in!” We let ourselves in, and found Andrew in the kitchen, putting a pizza in the oven, with drinks already out for everyone. We sat down at his kitchen island, and had small talk until the pizza was cooked. We then moved to the dining room, and enjoyed the pizza and more drinks, laughing and joking like we normally do, an I kind of forgot about the whole plan we had for tonight. We were feeling pretty good, enjoying the company, and decided to move things to the living room. We put on some music, Andrew pulled out a joint, and we continued to “party” like it was just a normal night. At one point Kayla gets up to go to the washroom, and for the first time that I can remember, Andrew doesn’t hesitate to check her out, not making any effort to hide it either, turning to me and saying “man she looks good tonight, I’m excited for what’s to come”. I smile and nod, still not sure what to say back.
When Kayla comes back to the living room, we both freeze. She’s clearly outside her comfort zone, and incredibly nervous, but she comes back into the room, and a set of Black lace lingerie, that I’ve never seen before. It has black garter’s and stockings, panties, that are clearly crotchless, and a corset with lace bra cups, dark enough you could just make out her little pink nipples. She was absolutely stunning, but also adorable, as she clearly was nervous, and was kind of hiding herself with her arms. We both complimented her in unison, giving her the confidence boost she required, where she stood up a little taller, and put her arms down to her sides. This is where I noticed for the first time, that she had shaved herself completely bare, and was clearly aroused, as I could see the shine on her thighs, and how red her pussy was from the desire.
She slowly walked over to Andrew and asked “Is this what you’ll imagined?”. He stood up, looking down at her, with a big smile on his face, and said “So much better”, as he leaned down to kiss her. I couldn’t believe what I was seeing, my best friend, making out with my gf of 8 years, who was also only wearing lingerie, knowing that this was only the beginning of the night. He was clearly excited, she was clearly excited. And we were just getting started.
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