The measure of 2 lovers is how they respond when you… | Part 1

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. Continue reading

The measure of 2 lovers is how they respond when you… | Part 2

For this to make any sense, you need to start with Part 1.

So now I have Andrew underneath me and Jason behind me. They start muttering about lube to each other and I know what will happen next. Even with my body being totally relaxed from the multiple orgasms I’ve now had, my brain is a little nervous.

Just before, I’d managed to have two cocks in my pussy (which, for the record, I’m told is generally pretty tight). But this is again new. After a bit of pressure, I was being double penetrated.

Continue reading

A mature FWB…really?!

I will confess I’ve gotten rather cynical (perhaps some would say, smart) about men in the last 16 months. I know within a few text messages if someone just wants to fuck or simply gets off on a hot chat. I know the guys who are players and the ones who are too needy.

What I don’t always realize is just how much this cynicism affects me. I now expect guys to be douchbags.

Obviously, not all of them are.

If you haven’t read about my threesome (with bonus mortifying moment) I suggest you do: Part 1 and Part 2.

Jason had made sure that he’d opened the door for Andrew and I to see each other again. He’d asked each of us individually if we wanted the other’s phone number. We both said yes, definitely. Ever the gentleman (although in this context I’ll concede it’s a bit weird), Jason told Andrew that I’m too good of a woman to not be satisfied on a regular basis, and therefore he didn’t mind if Andrew and I saw each other solo. Continue reading

I don't think I can have this Friend With Benefits

I write this from the town that Johnny Id and I visited when he was here at the beginning of August. I’m here with my Mom and some close friends.

The stores and places remind me of him. Then there was the man who looked EXACTLY like him sitting on a park bench. My Mom did a double take, as did I. We ended up seeing him multiple times over the course of the afternoon, and were even at the same restaurant for dinner. We’ve passed the hotel we stayed at several times.

I caught myself looking at gifts for his birthday numerous times. Then I had to give myself a shake and remember he’s not talking to me.

It happened more than once. I suppose it’s natural. All I can do is take one step at a time. Continue reading

Expecting disappointment & being pleasantly surprised

To get up to speed on Andrew’s story, you may first want to read about how we met, and our first phone conversation.

We settled on the following Friday to meet again, as it was the first night we were both child-free. Yes, he’s also a Dad, and he equally shares parenting with his ex-wife.

Usually I get frustrated at this point of meeting someone. After a date has been set, my typical experience is that I don’t hear from them, or its last-minute, and I find myself wondering whether the date is still on. I fight an internal battle whether to follow up or just leave it alone. It’s highly irritating. All you have to do is read some of my posts from last year this time to understand how I got to this place.

With Andrew, it was different. We texted a couple of times a day – not overly sexy but a few how-is-your-day-going and I-wish-you-were-there-for-my-morning-wood kinda things. On Wednesday he confirmed we were on for Friday, proactively. He asked what I wanted to do and I stumbled. Continue reading

The beginning of a new relationship – but what kind?

After my first solo date with Andrew, we spoke about when to see each other again. I tried to not be too presumptuous about what he wanted. I’m trying to be more careful on both sides.

From his perspective, I know he has a couple of others, and he has no issues with just casual relationships. I need to resist the urge to think his behaviour means something specific. Because that’s how I get hurt.

I will give you an example. I thought his making me dinner was really nice. Compared to some of the other men I’ve met, making me dinner would signify a major statement of how much I’m valued. And yes, I know how pathetic that sounds. But I’ve been with men who never thought to bring a bottle of wine with them, even though I hosted every. single. time. Continue reading

My mind is a jumble of naughty and heartache

I’m sitting in my vacation spot, outdoors, where it’s a bit chilly. I’m warming myself by a firepit. Listening to what I’m sure is a wedding party, and debating how uncouth it would be to crash. I’m also not wearing a bra, but am sporting a white shirt and realize that I’m a bit nipply.

As I think about what to write, there are many things going through my head right now.

The first (not foremost) is that my masturbation is getting naughtier. I find myself on occasion DP’ing myself. Is that odd?

Sheesh. Okay, here I am asking the internet if DP masturbation is weird. I guarantee that for every kink or idiosyncrasy, there is a community here. Continue reading

I'm more of a threat than his FWB

Last night Andrew and I spent a couple of hours on a skype call together. I like talking to him and I was also hoping perhaps he would talk me through a nice orgasm.

The latter didn’t happen, but we did have a great talk.

I forget now how it came up, but it was organic. I think I had said something about how stressed out I’d been, and he asked me if there was something else going on with me of which he was unaware. I suggested that work and home could be enough, but he knew better and pressed me on it.

I told him about Johnny – I had mentioned it in passing before; that I was coming out of a 6 month relationship – but hadn’t shared the intensity of my feelings. So I did. I told him I had been in love and it ended badly and why I had to make the decision I did. Continue reading

Hands and knees on the bed. Now.

A Skype conversation between Andrew and me:

Ann, I want to see the swimsuit you wore today.

You want to see the swimsuit? Okay, I will go get it….

No, I want to see you IN the swimsuit.

Okay sure, hold on a sec.

Undress slower. Mmmm…yes, that’s better.

Okay here it is. Do you like it?

Move the camera lower. Yes, that’s better. Now turn around.

Like this?

Lower. Yes, that’s better. Get yourself higher. Stand on the bed.

Like this?

Yes. God, you are beautiful. Get down on your hands and knees.

This bench is perfect. I wish you were here. How’s that?

Yes. Just like that. Mmmmm… Now, would you like to see what you do to me?

Oh fuck. That’s beautiful.

I feel terribly unsettled when I should be excited (Part 1)

I was going to write more about Faraway Lover today, but some things have happened with Andrew that leave me, well, unsettled.

He was nice enough to pick me up from the airport when I arrived home (yes, for those of you keeping track – he dropped me off AND picked me up). To make sure he wasn’t just being nice, I gave him a couple of “outs” prior to the actual date. He didn’t bite, so it was a plan. We agreed he would sleep over at my place, and have the morning together as well.

While I was away we spoke almost every single night – Skyped, to be specific. He doesn’t like to text so each day there were only a couple of text messages here and there, but one day I didn’t hear from him all day until I texted him late in the evening. He’s a real estate agent so I know he’s often running around and on the road, but still. Continue reading