first date surprise

Finding more things in common with Gregory.

The morning after my first date with Gregory, I was excited. It was a nice change to have had such a great intellectual and physical connection, with a man who seemed to be on the ball and in contrast to some of my recent experiences, well-balanced. Lots of commonalities to explore.

Even my Mom hadn’t seen any red flags in her internet searches.

I told myself to chill out and take Gregory as he comes. Given what I had been experienced with John, I was keenly aware there is reasonable excitement at potential, versus the crazy-town reaction of expecting everything is going to work out. I was determined to not give any impression I was like John. Because I’m not. I had no idea what potential we actually had.

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The night I didn’t plan to be beaten & have my first experience with a woman (1).

Imagine me last week:

Monday I was able to end my three-week long sex dry spell with a hookup at a sex club. Tuesday night I had crazy-but-empty sex with Lewis and then realized there was no future with him as he had been slowly fading away. Then I had a great night on Wednesday night with Tony, and acknowledged despite how I feel about him, there was no near-term future with him either. Tony and I were planning to have our talk on Saturday night. It was tentative depending on how his work went.

Thursday night I got home, fussed online, and watched television. I had met a couple of interesting prospects on Plenty of Fish who seemed normal, mature, articulate, and keen to meet. They met or exceeded my guidelines. But with plans on Friday to have dinner with a girlfriend, a potential date on Saturday with Tony, and then getting my son Liam on Sunday for the week, it seemed it wasn’t going to work in the near term. Continue reading

My gangbang fantasy became a reality – sort of (3)

Part One | Part Two | I went back downstairs in the sex club, where the main bar and activities were occurring. I was a little bit sex stupid and my legs were still shaky from the orgasms.

An ice breaker activity was about to start. As soon as one of the hosts saw me, she came over and enthusiastically asked me if I wanted to join. “Sure!” I said, and she led me over to the middle of three bar stools where I sat, flanked between a naked man with nipple piercings and a naked woman.

The man greeted me and I complimented him on his piercings. I asked whether I could touch one, and at the same time he said “oh I have a prince albert one too” so there was a little confusion and some giggles when I had to clarify I didn’t want to touch his cock. Continue reading

My gangbang fantasy became a reality – sort of (2)

[Part One] | I wore my unicorn necklace again, and packed the black string dress from Dale and Lisa, as well as a short black nightgown in case I wasn’t feeling as bold. I was ready to go to the sex club.

In the change room, I saw the same large breasted woman who complimented me on my shoes. She didn’t remember me, or if she did, wasn’t in the mood to chat.

As I was getting changed into the nightgown, I looked to my right and was pretty sure the young guy getting undressed was one of the men I was there to meet. He was taller, attractive, early 30s, and in good shape but nowhere near as ripped as his profile pictures. “Kris?” I said? And it was him.

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My gangbang fantasy became a reality – sort of (1)

The gangbang event finished. I woke up the next day with a terrible cold – which I felt coming on the day of the gangbang at the sex club, but chose to ignore it.

I am constantly amused at the dichotomy between my day-to-day life, and my sexual life. The gangbang was no exception.

It did not satisfy my sexual fantasies. It was fun, hot, and powerful. It was also disappointing, uncomfortable, and overwhelmingly weird.

Here is the setup to the event:

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A unicorn walks into a swingers club…5 & Final

Part One | Part Two | Part Three | Part Four

I think it was another first. Not just a new partner, but a completely anonymous partner. I didn’t get his name. He didn’t ask mine. He pounded away while I simultaneously orgasmed and thought that the edge of the platform was going to leave a nasty bruise on my legs (it did: several).

Dale and Jason were watching me, as were others. Jason said later he particularly liked the contrast between his dark skin, and my light.

Two funny things happened. While I don’t think he came, he just decided we were done after one of my orgasms. Perhaps he didn’t care that I could keep going – but to be fair, he would have been waiting a long time. He wandered off and I commented to Dale, Lisa, and the others, that “I guess we’re finished”.

Later, he came back to ask if he could fuck me again.

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A unicorn walks into a swingers club…4

Part One | Part Two | Part Three

I went to my locker to get changed. Not into the dress and heels I brought, but a dress – if you could call it that – given to me by someone at the club. It was essentially a bunch of string woven into a cool and very revealing pattern.

While I am definitely into sex, and feeling sexy, I have never been one to wear anything particularly revealing or what could be called slutty. This “dress” was the epitome of slutty. And I mean that in a very positive way.

So getting dressed was a rather quick affair. Arrange the outfit over my body. Ignore my underwear and shoes. Leave. Continue reading

A unicorn walks into a swingers club…3

Part One | Part Two

Dale helped me get situated by the deck. It was the three of us and one other couple. Everyone else has taken a break to go eat, before the real party started. One couple left saying they were going to try out the swing in the dungeon. Advice was shared on which end to put your ass.

I was mesmerized by Lisa’s breasts – also enhanced – as they bobbed as she talked. I didn’t find her particularly attractive overall (and yes, I have found a few women attractive over the years) but in some ways, it helped me be more comfortable. I wasn’t intimidated at all. She was, overall, rather normal.

I was constantly struck by the incongruous situation. The two naked couples were talking about their favourite camping spots, and we could have been anywhere. But given where we were, and the fact that everyone was naked (except me, with my boring black bathing suit bottom) the discussion turned to some questions on the practical challenges of being “in the lifestyle” and having sex in a camper. Because, of course, camper walls are paper thin and the whole thing moves when you are having sex.

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A unicorn walks into a swingers club…2

For Part One, click here.

What I failed to mention in my previous post was while in the afternoon, I was now scheduled to meet a couple “in the lifestyle”, that morning was my son Liam’s birthday party.

I’m sure I’m not the only one to feel this way, but I find the dichotomy striking between my sex life and being a mom and an executive in a really conservative profession. In moments at my son’s party, I found myself thinking “here I am, being a Mom, doing all the good Mom things, and this afternoon I may get f*cked by some new people. Multiple people. But right now, I’m handing out loot bags.”

Really weird.

I got home from the party (Liam was with his Dad) and had a few hours to kill before it was time for me to go. I texted Jason back and forth to confirm I was indeed, not chickening out. I did laundry. I figured out what I was going to wear. I did some planting on my balcony.

I definitely did things far more mundane than what could be considered appropriate pre-swingers club preparation. Continue reading