Weird Weekend Post #2: Awkwardest. Threesome. Ever.
Posted: 17 Nov 2014 23:29
This isn’t the first threesome I’ve posted and hopefully it won’t be the last, but it is hands down the most awkward.
Last Spring my friend Kelsey and I got into a discussion about music and sex. She is an accomplished classical cellist and works as a host for a weekly program on the local classical radio station in my city. Not surprisingly, Kelsey argued that the best genre of music to have really sweaty sex to was Classical Music, while I argued that the best genre of music to have really sweaty sex to was Something That Isn’t Classical Music. “Have you ever had really sweaty sex to classical?,” she would ask, and when I would admit that I didn’t think I had she would tell me that I shouldn’t dismiss what I hadn’t tried. We agreed that one day soon she would bring over some music she loved and “teach me how to listen to it,” and then see what I thought about having really sweaty sex to it. And then we kind of lost touch for a while. Life, ya know? I finally got a call from her over a weeks ago, and we got back to chatting every couple of days. She reminded me of the classical music lesson idea, and I said I was game -- but our evening schedules never meshed.
I was having coffee last Sunday morning when she called and asked if I was alone and it I had free time, and if so how about doing the music thing around lunch time? I agreed, and a few hours later she came over with cheese, crackers, strawberries, chocolate and an iPad with the music she wanted me to hear. I opened a bottle of sparking wine, pulled my guest-bed/futon mattress over to the living room part of my loft, hooked her pad up to my stereo, and we sat on the futon nibbling and sipping as she explained what we were listening to.
And then my door buzzer rang.
It was Barbara, who I have been seeing a bit lately but who was absolutely dropping by without notice. It was a little awkward as she walked in to see the spread and asked what we were celebrating. Kelsey explained that this was how she was teaching me to like classical music: relaxed with food and wine. So Barbara just kind of invited herself to join -- and then it sort of became this weird territorial grudge match between the two of them. Each was extremely sweet to the other, but each made it known without words to the other that they were each waiting for the other to leave first. It was a true detente, and so after the second bottle of wine was gone I began to get ideas...
In previous pillow talks, Barbara had confessed that although she had never been with a woman, she thought the idea was sexy and wanted to do a threesome someday with me. “But not a swinger thing where we make a date for group sex; I want it to happen organically” was what she said at the time. On the other hand, I had also had similar pillow talk with Kelsey, and knew that she had less than zero interest in either kind of threesome. “Doesn’t gross me out, but I’ll pass” was her point of view. But the wine was talking, and I got it in my head that I’d start making out with one and then the other and see what happened. Worst case, I figured, things would be uncomfortable enough that one of them would leave.
I kissed Kelsey first, because after all she was the invited guest. And then not long after Kelsey and I were kissing, Barbara scooted over closer and kissed my with a pretty deep tongue. We went back and forth like that for 5 or 10 and then I thought, what the hell? I told them I wanted to see them kiss one another -- and they did. And then they began to make out.
Still, it was more awkward that it sounds. And it went in a totally unexpected direction.
Kelsey actually got really into it, and Barbara seemed to barely hold back throughout the entire thing. They two of them kissed a lot, caressed each other, and used their mouths on the other’s nipples. But past that Barbara seemed to draw a soft line. If Kelsey put her hand between her legs Barbara would not object, and if Kelsey put Barbara's hand in between her own legs Barbara would do her best to pleasure Kelsey, but only for a minute before taking her hand away. There were a few times where Kelsey was kissing her way down Barbara’s body, and each time once Kelsey got past the stomach Barbara would reach down and coax her Kelsey’s back up to her breasts or mouth. Once, when Barbara was using her tongue quite expertly on Kelsey’s nipples, Kelsey began to softly push Barbara’s head down between her leg; Barbara resisted without saying anything, and Kelsey never tried again.
After about an hour I came pretty hard, and we all lay there for a bit. Then Barbara grabbed her clothes and said she had to use the restroom. Five minutes later, we heard the door open and close. “You should call her now, not later,” was Kelsey’s advice, and so I did. Barbara didn’t talk long. She just said that she was feeling embarrassed, and couldn’t decide if she was embarrassed because she just lived a fantasy and was disappointed, or because she liked it a little too much. She said she felt like she needed to figure that out before she tried something like that again, and that if she had stayed she knew that we’d go at it again before long. She also said she was embarrassed because she knew she had interrupted a date and had tired to sabotage it by hanging around. We agreed to try to reconnect soon.
Kelsey and I went back to music lessons and eating. After we’d rested a bit, we went back to sex. While the threesome part was pretty awkward, the twosome part was definitely not. I'll post that down below as well.
Kelsey now says she wants to try a threesome with another woman again with me, only with someone who feels more comfortable around her. She also says she wants to try a threesome with me with another guy. If those happen, I will of course post.
Enjoy.
Last Spring my friend Kelsey and I got into a discussion about music and sex. She is an accomplished classical cellist and works as a host for a weekly program on the local classical radio station in my city. Not surprisingly, Kelsey argued that the best genre of music to have really sweaty sex to was Classical Music, while I argued that the best genre of music to have really sweaty sex to was Something That Isn’t Classical Music. “Have you ever had really sweaty sex to classical?,” she would ask, and when I would admit that I didn’t think I had she would tell me that I shouldn’t dismiss what I hadn’t tried. We agreed that one day soon she would bring over some music she loved and “teach me how to listen to it,” and then see what I thought about having really sweaty sex to it. And then we kind of lost touch for a while. Life, ya know? I finally got a call from her over a weeks ago, and we got back to chatting every couple of days. She reminded me of the classical music lesson idea, and I said I was game -- but our evening schedules never meshed.
I was having coffee last Sunday morning when she called and asked if I was alone and it I had free time, and if so how about doing the music thing around lunch time? I agreed, and a few hours later she came over with cheese, crackers, strawberries, chocolate and an iPad with the music she wanted me to hear. I opened a bottle of sparking wine, pulled my guest-bed/futon mattress over to the living room part of my loft, hooked her pad up to my stereo, and we sat on the futon nibbling and sipping as she explained what we were listening to.
And then my door buzzer rang.
It was Barbara, who I have been seeing a bit lately but who was absolutely dropping by without notice. It was a little awkward as she walked in to see the spread and asked what we were celebrating. Kelsey explained that this was how she was teaching me to like classical music: relaxed with food and wine. So Barbara just kind of invited herself to join -- and then it sort of became this weird territorial grudge match between the two of them. Each was extremely sweet to the other, but each made it known without words to the other that they were each waiting for the other to leave first. It was a true detente, and so after the second bottle of wine was gone I began to get ideas...
In previous pillow talks, Barbara had confessed that although she had never been with a woman, she thought the idea was sexy and wanted to do a threesome someday with me. “But not a swinger thing where we make a date for group sex; I want it to happen organically” was what she said at the time. On the other hand, I had also had similar pillow talk with Kelsey, and knew that she had less than zero interest in either kind of threesome. “Doesn’t gross me out, but I’ll pass” was her point of view. But the wine was talking, and I got it in my head that I’d start making out with one and then the other and see what happened. Worst case, I figured, things would be uncomfortable enough that one of them would leave.
I kissed Kelsey first, because after all she was the invited guest. And then not long after Kelsey and I were kissing, Barbara scooted over closer and kissed my with a pretty deep tongue. We went back and forth like that for 5 or 10 and then I thought, what the hell? I told them I wanted to see them kiss one another -- and they did. And then they began to make out.
Still, it was more awkward that it sounds. And it went in a totally unexpected direction.
Kelsey actually got really into it, and Barbara seemed to barely hold back throughout the entire thing. They two of them kissed a lot, caressed each other, and used their mouths on the other’s nipples. But past that Barbara seemed to draw a soft line. If Kelsey put her hand between her legs Barbara would not object, and if Kelsey put Barbara's hand in between her own legs Barbara would do her best to pleasure Kelsey, but only for a minute before taking her hand away. There were a few times where Kelsey was kissing her way down Barbara’s body, and each time once Kelsey got past the stomach Barbara would reach down and coax her Kelsey’s back up to her breasts or mouth. Once, when Barbara was using her tongue quite expertly on Kelsey’s nipples, Kelsey began to softly push Barbara’s head down between her leg; Barbara resisted without saying anything, and Kelsey never tried again.
After about an hour I came pretty hard, and we all lay there for a bit. Then Barbara grabbed her clothes and said she had to use the restroom. Five minutes later, we heard the door open and close. “You should call her now, not later,” was Kelsey’s advice, and so I did. Barbara didn’t talk long. She just said that she was feeling embarrassed, and couldn’t decide if she was embarrassed because she just lived a fantasy and was disappointed, or because she liked it a little too much. She said she felt like she needed to figure that out before she tried something like that again, and that if she had stayed she knew that we’d go at it again before long. She also said she was embarrassed because she knew she had interrupted a date and had tired to sabotage it by hanging around. We agreed to try to reconnect soon.
Kelsey and I went back to music lessons and eating. After we’d rested a bit, we went back to sex. While the threesome part was pretty awkward, the twosome part was definitely not. I'll post that down below as well.
Kelsey now says she wants to try a threesome with another woman again with me, only with someone who feels more comfortable around her. She also says she wants to try a threesome with me with another guy. If those happen, I will of course post.
Enjoy.