My second threesome | 1996

I have said on numerous occasions I would write about my threesomes. My first was when I was 18, and it occurred on a beach with #10 of the Men I’ve Slept With. I will write about it but need to find that journal.

I think I will just let my journal tell the story. I was in university, nearing graduation, and had met an actor who I was head over heels in lust with. He was #30 of my sexual partners and was the best lover I’d had so far. I guess he was my first real FWB, since I knew he wasn’t exclusive but we would hang out and occasionally have sex. We had worked on a few shows together, as had the third player in my story.

Here is my second threesome, straight from my journal:


It was the second Wednesday of the run and a bunch of us went out afterwards to the bar. We all drank for a while there, and Stewart, Scott and I smoked up a couple of times, then we all went to another bar to play pool.

At some point Scott, with whom I had had many conversations about threesomes, said to me “don’t you think this is a little weird, this you, me, and Stewart thing?” To tell the truth, it hasn’t occurred to me at that point, but it certainly did then! I played a game of pool against Stewart, who is very good (but I didn’t do too badly either) and we all had another pitcher. Scott and I were flirting pretty heavily, and he even pointed it out to me.

One thing about Scott, when he’s stoned or drunk, he talks a lot. He always has stories and puppet shows and all kinds of stuff like that. But he’s also the most incredibly perceptive person I’ve ever met. He always knows exactly what I’m thinking. I can never hide my motives from him. It can actually be very annoying because I can’t be coy or deceptive. He calls me on anything like that. It’s good practice for being honest, though!

So…we closed the bar down, and we all decided we weren’t tired, so, go figure, we decided to go to my place because I had more weed. By this time Scott was really giving me the “what the hell are we doing” look. We hung out, played music, and smoked up again. Scott did a puppet show for Stewart and I, then we ended up sitting on my bed. I went to the bathroom and (later) found out that the boys were asking each other if anything was going to happen.

They decided that Scott would be the “lead man” and let Stewart know if things were cool for him to get involved. Stewart was ready to go and Scott told him to stay because he thought “it” was going to happen.

So – the question remained. How does one begin a menage a trois? It was pretty clear that we all wanted stuff to happen, but of course nobody wanted it to be too obvious. So we were all searching for a way to begin things.

Scott’s idea, which was mostly successful, was to “shotgun” a joint. One person inhales and then blows it back into the mouth of the other. So, Stewart inhaled first for me, but we didn’t really kiss. Then Scott did, and of course we ended up kissing. We didn’t stop, and Scott because asking me if it was okay for Stewart to touch me, then kiss me. I said yes, so Scott motioned (although I couldn’t see him, he told me later he did) to Stewart that everything was okay.

So, that’s how it all started.

My first threesome experience was nothing compared to this. How incredible! I don’t even know how to describe the experience on paper. Both Stewart and Scott’s attention was completely focussed on me. I did things to them as well, but…it just wasn’t the same intensity. And I can’t even count how many times I had sex or how many orgasms I had.

Stewart wasn’t a bad lover, but Scott was definitely the lead man. Wow.

Sometime in the morning we all went to sleep, and I woke up a couple of hours later between two guys. Scott and I were holding hands and Stewart had his arm around me. It was so cool, I must have had a huge Cheshire cat grin on my face.

We all woke up eventually, and decided to go for breakfast. The three of us went out. We all looked so relaxed and evil at the same time. The jokes flew.

We had two toasts – the first to an evening which none of us would ever forget, and the second to an amazing, incredible experience. Both Scott and Stewart talked about how wild it was to watch someone else have sex. And how great it was to watch me (neither of them had any interaction with the other). They both thanked me (although they definitely were the ones who deserved the glowing thanks) and treated me to breakfast.

After breakfast we decided to go back to my place (we were due at the theatre in a couple of hours anyway) to sleep and shower.

Scott and I took a shower together, having great sex in the process, then both came back to my bed, where Stewart was trying to sleep. I lay down between the two of them, and tried to nap.

Sure enough, we were all at it again. I had sex with Scott while I gave Stewart head, until they both came. Wild. We fell asleep for a while after that, then got up to go to the show.

We arrived at the theatre together and who should we run into but Matt, who knew we had all gone back to my place. He began harassing us immediately, so I went inside so that more people wouldn’t see our entrance together.


That wasn’t the last time the three of us had sex together. It also led to an awkward moment when Stewart thought he could have me on his own.

More to cum come.

0 thoughts on “My second threesome | 1996

  1. Wow, Ann. Leaving out the “dirty” bits invites imagination. However, it feels like you “yada, yada’d” over the best parts. Now I am worried that my wife is going to read your post. 😉

      • Your “next threesome.” Ok, that is sexy.Neither my wife nor I have any concept of this. Probably never will (neither of us has ever been with anyone else…period). I know…we’re strange. 😐

        • Not strange at all, actually. I think here in blog land you can get a very skewed sense of what most people’s lives are like. I am hard pressed to think of any of my female friends who have had a threesome – nor do they have the desire.

          But yeah, it’s a plan for me to have more of them. I didn’t write about the one with Johnny because it wasn’t at all what we thought it would be (he wrote about it, though). But Jason and I are talking about doing it again.

          • Yes, skewed. That is exactly what I have been feeling. However, I do know that the intimate activities that my wife and I do (that I blog about) is probably more foreign and considerably more taboo than the threesome.People like to read about it but they certainly don’t want to talk about it. 😉

            Where I know that my wife and I are strange is that we met and started dating in high school (at 16 years old) and began our sexual intimacy then. We are both less than a year away from 50 and neither of us has experienced any sexual contact with another (I did get kissed and aggressively fondled by a gorgeous and sexy female colleague during an industry business trip that I had – but didn’t want – to back away from). So, no other lovers for all of those years.

          • Well first of all, your wife is smokin hot for 49. I wish I had that body (and I know she works hard for it…whereas the gym and I have not been acquainted for several months).

            But you are absolutely right – it’s not many couple who have stood that kind of test of time. Congratulations 🙂

          • I have to contest…she is smokin’ hot. Period. 🙂 She is going to be blushing like mad when she gets online and sees this dialogue. 😉

            Thank you, Ann. I know that what we have is unique (especially when the marriages of our friends and some family are fracturing all around us).

          • Oh…look what we have done to you (and Sharn). You’re qualifying your statement (about the photos). 😀

            Watch out…when my wife sees this thread, you might be receiving an email with a link. Did I mention that she’s having too much fun with that? 😐

          • No, not to my knowledge. You do realize what you are setting yourself up for, don’t you? Not only are you going to be accosted by an overzealous 49 year old, highly aroused woman, but you are going to make my evening a decidedly long and tiresome (yet extremely enjoyable) affair.

            Lest you think I jest. Yesterday, a fellow blogger asked for her to send the link. She was checking incessantly to see if she (the blogger) responded. We were in bed and she had the smart phone in her hand, waiting and checking for a notification (which finally arrived) during our intimacy. 😐

            If you knew her before, you would be blown away by how much she is enjoying this.

          • Uh, sweetie…first off, we aren’t going to be having a threesome anytime soon. You need to put that out of your mind. Now. Second, Ann is not me (be thankful, Ann!). Thirdly, you have me, Mr. WC! Besides, I don’t think that you have the stamina to do what we do together to add in another person (or perhaps, I am lacking). Onward!

            Ann – thank you for your empowering comments. OMG that means a lot coming from you! I certainly don’t feel like I am approaching 50, but it is the plain and simple truth. Both Mr. WC and I commit a lot of effort to being fit for each other and the rewards in the bedroom make the pain and sweat worth all of the work.

            Yes, I have been getting very excited about our picture sharing. It is has been the most amazing antidote to the ills of my life long suffering from body image issues! Yes, Mr. WC is correct. I do love to share. 🙂

          • Ouch! I wasn’t implying that WE should seek out adding people to our bed. Sheesh. Apparently, you are under the assumption that you have developed the ability to read my mind. 😉 (I do love you, Mrs. WC, with ALL of my heart)

            Watch out, Ann. 😀

  2. Wow…that’s pretty awesome that you shared such an intimate moment. Sounds like you found two mature guys to do it with, too. I think that must make all the difference.

  3. Like Hollie, I’ve never had a threesome. Close once or twice way back when I was in college but it didn’t happen, and I’m sure it’s because of my own body image issues amongst other things. As I’ve gotten older though, especially in the last two years with him, I fantasize about a MFM threesome. Thanks for sharing, as always!

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