It was just another Sunday, like any other Sunday. Being single and carefree, I came and went as I pleased. That usually meant going to see my friend Kim at her music gig down on Carleton Street. It was always a jam, so you never knew who you might see there, but really it was a gig that she played mostly herself and the band she assembled.
On this Sunday, there wasn't much of a crowd. By the end of the third set it was becoming dark. I had taken the subway down to her gig, as I did most times I went to this gig, and was about to prepare to head home. Taking the subway in this case would come back to haunt me as the day progressed and events unfolded.
As usual, I sat and chatted with Kim for a bit.
"Hey, got any plans for tonight?" she said.
"No, just gonna go home and hang out" I replied.
"Why don't you come to my gig tonight, it should be a good one" she said.
I knew when she said that it usually was. Kim played the best and most interesting venues and there were always interesting people to meet. At the very least anyway there would be great music to listen to, since she always delivered that.
She had her car, we packed her gear into it and off we went to the gig. We stopped for dinner first, as there was a two hour gap. We shot the breeze and had a couple of burgers. She asked me if I was seeing anyone. I told her that I wasn't. She was still dating Barry, but it was going nowhere. He would be at the gig tonight so she would be preoccupied with him.
It had been about a year since I met Kim. She wasn't really my type and we really connected on the music end of it. She saw me writing at one of her gigs and came over and asked me what I was writing. When I showed her she liked what I had written and asked if I also sang. She commented that based on my speaking voice I would probably make a good singer as well, and we made a time to meet up at her place to work on the new songs and see if I could sing a bit. She was also a voice coach.
That time when I came over to her place, it was a quaint one bedroom basement apartment. She welcomed me in and we worked on a few songs I had brought. We sang them together. Obviously she was a major singing talent and I was not, but we could harmonize together. She got the melody of the lyrics that I was looking for.
As the night progressed she made me some coffee and we took a break and moved to the couch.
We continued to work on the songs, and we were sitting close. She was dressed relaxed, just a sweatshirt and track pants, and definitely no bra. She was a bit overweight, and not really my type, but she did have very large breasts and I noticed that a bit more this time.
She leaned into me..and we were very close. Our hands were touching and we could both sense that. She continued to lean into me..and I could feel her nipples were hard and against my arm. We both knew that and neither of us was backing away.
She looked up at me and we began to get closer and leaning towards a kiss. As we began to kiss, there was no hesitation on either side. Things were moving very fast and she moved my hand under her sweatshirt and onto her breasts and I could now feel with my fingers how taut her nipples were. There really was no turning back now.
She grabbed my hand and led me to her bedroom. As we got there, she stopped and I was directly behind her. She put both of my hands under her sweatshirt and I was now caressing both of her boobs with both hands as she leaned back into me.
"I have been thinking about this and waiting for this since the first day we met" she whispered into my ear as I lifted her sweatshirt off.
She then turned towards me and lifting off my t shirt and began kissing my chest, stopping at my nipples to suck them lightly as well. It was clear that her sultry and sexy singing was not limited to only singing.
She kept right on going and pulled my track pants off and had no hesitation as she began to suck me. I was very hard and erect and we both knew where this was going and had no intention of stopping it. It wasn't love, but it was pure lust. She did have big beautiful soft lips..and she knew how to use them.
She leaned back on the bed, and now I began in earnest to please her. We kissed for a bit while I was on top of her, completely naked, while she had now removed her track pants but still had her panties on. As we kissed I could feel how wet she was under those panties and my tongue was longing to be there to taste that.
I moved down her neck and began kissing her nipples, moving them together with my hands as I used my tongue to tease the area just below her nipples. I was very hard now and my cock was pressing against her mound that was still under her panties.
The sight of her very large breasts being kissed by my lips was more than I could stand. Although I really wanted to lick her pussy and tease her clit, in this case it was too much to wait. I quickly removed her panties and entered her in one shot, something I guess she didn't expect and she shrieked. We made passionate love for over an hour, and it was everything you would expect from a passionate woman like her.
After we were done, we went back to the living room and carried on with our writing for another hour, then I left. We never spoke about that again and it never affected our friendship. But I always got the impression that she had spread it around that I was a good lover, because many of her friends seemed more friendly after that day.
We got to the Kim's evening gig an hour early, so I hung around the bar. I noticed a different kind of vibe at this bar. Wasn't sure what it was, but it was different for sure.
The band got set up and the crowd started to roll in. It then became apparent that there were a significant amount of gay men at this bar. It wasn't a gay bar, but for whatever reason most of the men were gay..and younger. Being 100% straight, this made me slightly uncomfortable, but it wasn't the first time Kim had led me into this sort of situation. As usual, I just ignored it and minded my own business. As it turns out, the gig was sponsored by a group of Gay And Lesbian people, so it the turnout was hardly surprising.
There were also a few of Kim's women friends there which I knew from her other gigs. As the music began to play and many were dancing, I danced with Michelle, who I had always had the hots for and who had made a pass at me once at another gig. I did kiss her that one time, but it never went anywhere from there. She was significantly older than me, and we just didn't mesh enough to make it worth doing any more than that.
As we sat back down at our table, another young guy, Kurt, was sitting there. I was in my late twenties, but he was clearly 18 or 19. And he was obviously gay. He seemed like he was also a nice guy, and we chatted a bit. A few times he got up and danced with a few guys but he kept coming back to sit at our table. I danced a few times more with Michele, and we kissed again one or two times more, a little more passionately than the other times, but again, other than feeling her up a bit, it wasn't going anywhere.
I had always wanted to do more with Michelle, and I knew that she would have been willing. That first time we kissed she needed a ride home and I could have given her one. If I had I was sure she would have invited me in for a nightcap, and much more. She had a smoldering passion and sensuality you find in only a handful of women in your life. She also was drop dead gorgeous and had a great smile, but it was that inner passion and sensuality that drew me to her. That one kiss we had confirmed that. It was very tender and sensual, and we certainly had a sexual chemistry. She also wasn't shy and was clearly letting me know she wanted more.
But that is a story for another time.
As Michele and I made our way back to the table, Kurt was now talking to a woman. A very attractive older woman, somewhere in her mid to late 40s. She introduced herself to me as Karen, and as we chatted a bit she let me know that she was Kurt's mother. I commented that she couldn't be his mother, because she was so pretty and so young looking.
"This whole place is filled with gay guys" she blurted out to me.
Just as the next song came on, a slow song, she grabbed my hand and dragged me onto the dance floor. As we danced close, she certainly wasn't shy and pressed her boobs firmly against my chest and was caressing my behind.
"Kiss me" she said.
And we did. It wasn't a long or passionate kiss like with Michelle, but there were definitely sparks. We then sat down back at the table, as she led me back there we were holding hands.
We danced again, this time the kisses were longer and more involved. The song seemed to go on forever, and neither of us really noticed.
As the first set ended, we sat down and Kim came over to schmooze. Karen was there and was talking to Kurt. We all ordered food, and Karen and I shared a bit. Under the table, we were rubbing hands and she put my hand down under her skirt and towards her pussy, which was already very wet. She looked me in the eye as she moved my fingers inside or her. She was careful enough to make sure others couldn't see what we were doing, most specifically Kurt, but Kim and Michelle were looking at me, and they knew. However they both smiled at me and said nothing.
The second set started, and Karen and I danced again. This time it was much more friendly. As we sat down, she said she was going home and asked if I wanted to join her. I didn't have a car, and neither did she, so she hailed a cab. As we got in to the cab, a third person, a woman who clearly was a lesbian, a butch lesbian, got into the cab with us. This startled me, but Karen seemed to know her, so I wasn't terribly concerned.
The ride over to her condo was interesting. I didn't really know Karen at all, and her "friend" was certainly not my type of person to hang out with. I did feel a bit uncomfortable being in the cab with them, but I just rolled with it.
As the cab arrived at her building it was obvious she was a very rich woman. This was the type of building you usually see from the outside but never get to go in to. We all got in the elevator and went up to her condo, which was on the penthouse level. As we got in the apartment, the butch girl (Jesse) and I sat on the couch while Karen went to her bedroom. I really had no idea what to expect next. I wasn't nervous, but I did feel uneasy. I was with two women I only knew for less than two hours and who seemed to be a bit erratic.
Jesse and I really had nothing to say to each other. We both knew that we were there for pretty much the same reason: to fuck Karen, but neither of us wanted the other there.
Karen came out of the bedroom in a see through nightgown, and sat on the couch. We started to make out, and Jesse was just watching. She said nothing and did nothing. This went on for about 10 minutes, and we were at the point where Karen and I were about to get naked.
Suddenly Karen got up and told Jesse she had to leave. But she didn't seem interested in that. They got up and argued a bit, then Karen led Jesse to the door and began to push her out and closed the door.
She came back to me and sat on the couch. We made out some more and I pulled the top of her nightgown off and began caressing her breasts. They were average size, but for a woman her age they were very perky and soft. Possibly the softest I remember of all the women I had been with to that stage and since. It was obvious she hadn't been touched in a while and was in heaven when I began to suck her nipples until they were very hard.
Just as we were about to go to the bedroom Jesse began banging on the door. We ignored her for a minute or two, then Karen went out into the hallway and they argued. I still to this day don't know why Karen brought her up to the condo, but I suspect that it had something to do with her son. After about 10 minutes, Karen came back into the condo and Jesse was gone for good.
This time though, we stopped kissing and were just lightly touching and we talked for about an hour. It had been a long day and was close to 1am by this point. The talk was very intense and we learned a bit about each other, then started to kiss again and since she didn't have any panties on I had my fingers inside her. She said she wanted to go to bed, and wanted me to tuck her in. I said ok.
All of my clothes were still on, but as we entered her bedroom, she lifted her nightgown up over her head and was completely naked. She got under the covers and told me to tuck her in. So I did. As I was just about finished pulling the covers on her she grabbed my neck and started to kiss. She then whispered in my ear
"I want you to make me cum"
It was very late, and I didn't have any condoms on me. I wanted to be inside her very badly, but what could I do? I asked her if there were any drugstores open at this time of night, and she said no. We continued to make out and as we did she slipped my pants and underwear off. I was now this close to being inside her, but didn't . I rubbed my cock up against her clit, enough to excite her, but never penetrated. This went on for quite a while and we were virtually making love, but never actually had intercourse. At one point I did remove all the covers and went down on her for about 20 minutes, until she came multiple times.
I looked up at the clock and it was now 2:15. I said I had to go. She said wasn't there any way I could come inside her, and I said no, but that I could come back the next night and finish the job. She gave me her number and said to make sure I called.
It wasn't until I got down to the lobby and onto the street that I realized the subway was closed and I only had 20 bucks left in my pocket. My only option was now a taxi, and it was going be an expensive ride. All the way home, all I could think about is that I wished I had a condom in my wallet. But I didn't.
I called her the next day, left a couple of messages, and never heard from her again. I still think of her, and how I wished I had fucked her. I also think how lucky I was that Karen and Jesse didn't rob and kill me. It was quite a night, one I will never forget.