What is the worst thing that has ever happened to you during sex?
Have you ever had a threesome with two members of the opposite sex?
Any of you have that worst thing happen DURING a threesome?
You getting where I’m going with this? Good.
Let me break it down for you.
Jason, who I have known for almost a year, has been a steady presence but infrequent lover. I’m the only woman he’s had sex with since we met. He joined me and Johnny for our threesome.
Jason and I have always talked about a mutual desire for threesomes. Before I met Johnny, Jason had found someone for us but it got cancelled at the last minute, when he got delayed at work. When I told Jason that Johnny and I had opened our relationship back up, he resumed his search.
Jason happens to be bi-sexual. Or at least, he will have sex with guys when there is a group involved. I don’t know if he’s ever had sex with a guy on his own, but I know he and a previous girlfriend would “play” on a regular basis with another couple.
So his strong preference was for the two of us to play with another couple. I wasn’t quite ready to share my bits with another woman, so he agreed to start with a man only.
We got together a few weeks ago and he told me he’d found our third – we’ll call him Andrew. He showed me a picture (attractive and intense looking). During sex, he snapped some pics to share. Andrew happens to also be bi-sexual. He and Jason have fucked each other before.
Jason’s time is pretty limited, just like mine. But we managed to find a night – well, a two-hour window – when we were all free. I was hosting.
Here’s how it went down (pun intended):
Andrew shows up before Jason. He is shorter than me, and smaller – but fit and attractive. It’s a little awkward – my internal monologue was constant laughter at the ridiculousness and naughtiness of it all – but I invite him in and offer him a glass of wine.
He’s older than me, divorced with a young child, and a good conversationalist.
Jason is running a bit late; he texts that when he shows up he’d like me to be sucking Andrew’s cock. He also wants me in something “skimpy” – I tell him too late, but I’m wearing some great lingerie.
It’s hard for me to go from a work conference call to spontaneously sucking some new dude’s cock. Perhaps it’s just me.
Jason shows up and spends more time in my living room than he ever has before. We joke about that. It is very odd to have two guys talking about having sex with me. Andrew says “Jason, how could you not have told me about her ass!” as he gives me a playful smack as I walk by. For the record, I LOVED that.
Jason – who had flown in from a different city that morning – says he’s going upstairs to take a shower. I follow him to provide a towel. We kiss for a bit, and he tells me he’s not coming back downstairs.
Okay, we are now on a timeline.
I relay this information to Andrew. He asks me if I’m shy and I explain nope, just feeling a little awkward.
He leans forward to kiss me. It’s a great kiss. I invite him upstairs. As we make it to my bedroom, Jason is coming out of the bathroom.
Andrew comes at me and starts kissing me, his hands roaming everywhere. He undresses me, then grabs me and moves me to the centre of my room where Jason can also have access.
The next thing I know, there is that wonderful feeling of four hands on me and two mouths on me. I wish I could recount it play-by-play, but there was just too much going on.
Andrew is kneeling between my legs, Jason is behind me, with his mouth on my neck and his hands on my breasts and hips. They are both perfectly dominant, moving me where they want me, adjusting positions and talking about what they should do next.
I get put on the bed, perpendicular. I’m told to get on my hands and knees. Andrew slides underneath me and puts his face between my legs. I take his cock in my mouth – it’s large and thick and truly beautiful. Jason stands behind me and starts fucking me. Oh. My. God.
My descent into being just a writhing mass of sensation starts right then. Any semblance of rational thought is gone. Forget any decisions of my own. It’s just about the pleasure.
And boy, was there a lot of it.
I had asked Jason in advance whether he and Andrew were likely to have sex – and he said nope, this time it was all about me. I really didn’t know how I would feel about seeing two men be intimate.
Turns out, it didn’t bother me at all. It was rather hot. They didn’t fuck but:
- At one point Jason withdrew his cock from me and Andrew immediately took it in his mouth.
- When I needed to use both arms to keep myself upright, Jason grabbed Andrew’s cock so I could keep it in my mouth.
You see? It was handy!
So…we switch positions a few times. Jason knows that I wanted to experience both kinds of double penetration. He’s on a mission. I’m completely lost in my orgasms. Jason is underneath me and Andrew is behind me. The next thing I know, I feel extra pressure, but no pain. I hear Andrew saying “Jason are you still in?” and I realize that both their cocks are in my pussy.
I look down at Jason and say “are you both…”? He winks at me and grins. I say “how is that even possible?”, giggling like a crazy person who is also having an orgasm.
It doesn’t hurt. I’m shocked.
After a while they switch positions and that’s when the shit gets truly crazy.