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First times  

Insindiary 52M
263 posts
6/17/2011 3:42 pm
First times


Rand had another party last weekend - his biggest of the year. It was literally themed as a Roman orgy. All of his guests, to include Tricia and I, came dressed in togas.

It was a large crowd, and most of the regulars were there. At 10:00, Rand read his rules, and then everyone got naked.

Maggie and I didn't waste any time in playing together on a futon mattress in Rand's living room. "Living room" might not be the best description. Rand lives in a studio apartment. Only the bathroom and a storage closet are in separate rooms. Otherwise, everything is open. Even the bedroom is only separated by a wall. When you're having sex at his place, you're having it in front of everyone.

Lexy and Daisy started playing next to us. They are both regulars at Rand's. Lexy dated Maggie for a year or so. They don't date anymore, but they still play together. After Maggie and I had fucked for a while, Lexy joined in with us. Lexy and I both started to rub Maggie's body and suck on her nipples. Maggie was in heaven, but she literally pushed Lexy and I together at one point, and slowly eased herself out from our threesome.

Lexy is a pixie-like nerd chic girl with a rocking body. She usually wears multi-colored toe socks to Rand's parties, and nothing else. She is adorable. In most of my blog posts about these parties, I've talked about women I would like to have sex with, but never really found the enterprise to ask. Lexy is one of those women.

In a way, it's the sort of thing I've been waiting for - for me to just find myself in a sexual situation with someone who obviously digs me, and Lexy did. Maggie had, in fact, hinted earlier that Lexy was very interested in fucking me.

So, we fucked.

And it was almost completely pleasureless for me.

Lexy enjoyed it very much, and made some nice noises. I held on to the back of her neck, and fucked her hard on her back. I didn't cum, which is the norm for me. After a few minutes of that. I told her to turn around and I would do her from behind. But, at that point, I had lost my erection just enough that I couldn't put it in her. I stroked myself while I fingered her. Maggie mercifully entered the fray again, and distracted Lexy while I tried to get myself hard. It just wasn't happening for me, and, luckily, both Lexy and Maggie chose that moment to take a break.

"You're fun," I told Lexy. I didn't feel a lot of enthusiasm for the statement, but it was the right thing to say.

"You are too," she told me. "I always wanted to play with you but I couldn't talk to you." She said this last part as if it were a simple fact and needed no further explanation.

"What?" I asked. "Why couldn't you talk to me?"

"Because you're so hot," she said.

She really had me flustered with that statement, and the whole scene was a bit weird - being in a room full of naked people, talking to a girl I just had uninspired sex with. Lexy is a little hottie who I doubt has seen 28 birthdays. And here she was, telling me I'm too sexy to approach. I felt stupid, and flattered, but mostly stupid.

"I... don't... think of myself that way..." I started to mumble to her, but her attention had already been pulled away by something Maggie said. Lexy and I parted as friends that night, but we didn't really talk much after that.

I began to think about how withdrawn and timid I am around the other people at Rand's parties. The other people seem fun and confident and interesting. My short talk with Lexy turned some of that inside out. That's how they see me. For as awkward and shy as I feel around them, it occurred to me that maybe they feel the same way. Of course I had considered this before, but it's hard to believe. I KNOW how shy I am. It's hard to believe OTHER people can be that way.

It may not be entirely true of everyone at the party, but it made me look at them differently. It made me feel that maybe some of them needed me to talk to them; to show some interest, to give a compliment, to simply acknowledge them. These are the things I secretly want from them.

I can't say that this little epiphany will change things much. The parties are still too overwhelming for me. I'll always get lost. But maybe I'll have a bit more confidence. Lexy was great for my self-esteem.

I also know that I can play in a way I've been wanting to - to just kind of jump into sex with someone new without a lot of preamble. The result this time was... not great (and part of me must have KNOWN it would be that way, which may explain why I didn't try harder to do it).

Still, I would like to have sex with Lexy again. Let's face it - first times are almost always bad.


christylovesfun 51F  
16880 posts
6/17/2011 4:26 pm

So, it outsides the bounds of your relationship to have sex with her one on one?

Age cannot wither her, nor custom stale
Her infinite variety. Other women cloy
The appetites they feed, but she makes hungry
Where most she satisfies. For vilest things
Become themselves in her, that the holy priests
Bless her when she is riggish. ~~ from Antony & Cleopatra


playful64more 60F
1425 posts
6/17/2011 9:21 pm

It's hard to imagine you as being so shy when you are so completely open here. I am glad you made some progress and hope you keep this in mind in the future.

I AM RESPONSIBLE FOR MY OWN HAPPINESS!! (MY LIFE'S PHILOSOPHY)


Insindiary 52M
153 posts
6/18/2011 11:02 am

    Quoting christylovesfun:
    So, it outsides the bounds of your relationship to have sex with her one on one?
Not at all. I could and would be with her one on one.


Insindiary 52M
153 posts
6/18/2011 11:09 am

    Quoting playful64more:
    It's hard to imagine you as being so shy when you are so completely open here. I am glad you made some progress and hope you keep this in mind in the future.
It's a little more complicated than just being shy. I'm also just not that motivated to play with new women. When Tricia and I started in the lifestyle, I wanted to have sex with everyone. These days, I'm happy to play with women that are familiar to me, and I'm not really looking for someone new. So it feels like I should be more aggressive. I don't think the other people at the party are as conflicted. They simply want sex. And I'm someone who shows up often but just doesn't give it up. Then I feel I little guilty. As you can see, these parties stir up a beehive of emotions in my brain, causing me to just kind of withdraw.


christylovesfun 51F  
16880 posts
6/18/2011 11:22 am

Then hook that shit up! Have fun!

Age cannot wither her, nor custom stale
Her infinite variety. Other women cloy
The appetites they feed, but she makes hungry
Where most she satisfies. For vilest things
Become themselves in her, that the holy priests
Bless her when she is riggish. ~~ from Antony & Cleopatra


TheRedheadinHeat 62F
9294 posts
6/18/2011 3:09 pm

We are not anywhere in the same vernacular, but when next you are in ATL, let's meet up for a drink and chat. I have been reading you for a few years and it would be interesting to meet the person behind the worlds.

If I have stopped by your blog, please be sure to sign my permission slip Pimp Me, Pimp My Blog, But Let Me Do The Same With You


Insindiary 52M
153 posts
6/18/2011 5:43 pm

    Quoting TheRedheadinHeat:
    We are not anywhere in the same vernacular, but when next you are in ATL, let's meet up for a drink and chat. I have been reading you for a few years and it would be interesting to meet the person behind the worlds.
That would be nice. I have no idea when I'll be there again.


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