The One with the Threesome

I am in my 50s and semi-retired from the Game, so I'll just share some stories culled from over 25 years of being a chaser:

Over the last 5 years I had started trolling gay clubs to meet TS. The street action had died down and there were fewer and fewer clubs that catered exclusively to the TS community. I had discovered that some gay clubs usually had a couple of TS, but they were usually there to hang out with friends and were not as aggressive as the girls in the TS-only clubs.

In San Francisco, my favorite spot to troll was the Badlands club in the Castro District. On a good Saturday night, I could expect to see about 5 TS in a club of over 100 mostly gay guys with some lesbians and straight people.

One night, early in the evening, I was standing in Badlands when I noticed a tall, thin Asian-looking woman with long black hair in a tight-fitting yellow dress. I took a swig of my drink and tried to muster up the courage to get closer to her.

As I got closer to her, she noticed me and started dancing towards me. We smiled at each other and started talking. Her name was Michelle (name changed). She was filipina, was there with some friends, had a 9-5 day job, and just liked to dress up as a girl on the weekends.

She was very flirtatious and even grabbed my crotch. Naturally I am rock hard and hoping that something will happen that night. Of course, her gay friends show up and I spend most of the time chatting with one guy who I think thinks I like him. Somehow I ended up with the gay friends' number and Michelle and her friends left the club. A couple of days later I texted the gay friend asking about Michelle but no response.

Over the next several months, I would run into Michelle at Badlands a couple of times. We would chat, she would flirt, I would meet her friends, but she would never go home with me or let me take her out on a date.

About a year after I first met Michelle, I had just started dating an attractive GG. I really liked her and was hoping something would develop. The GG was out of town one particular weekend so I decided to see what was happening at Badlands.

I got to the club around 11:30 and I ran into Michelle. She was already wasted. After a year of prick teasing, the floodgates were now open. We started making out in the club. She pulled me in to the bathroom where she pulled down my pants and started giving me a blowjob. In front of other people (guys and girls) in the bathroom!

Michelle was ready to get laid! She wanted to leave the club now!

For some reason, Michelle brought along a male friend who was dressing up for the first time. His/her ensemble was just a blouse and heels and a wig. Not passable but there was some femininity since she was also filipina.

The three of us grabbed a cab and Michelle was insatiable. While in the back of the cab she was pulling on my pants and ready to give me another blowjob. We finally arrived at my apartment building, left the cab and headed upstairs to my unit.

Once inside, I realized we had 3 people. How would I keep the friend engaged and not want to leave while I was having sex with Michelle? I know! Why not a threesome?

I invited Michelle and the friend in to my bedroom. We each took off our clothes and jumped on my bed. I started kissing Michelle. Every now and then I would kiss the friend to keep her engaged.

Next, a round of blowjobs for everyone! Michelle sucked me, I sucked her, I may have sucked the friend. We were kissing each other, touching, fondling, caressing, sucking, everything. Surprisingly, I was feeling more passionate towards the friend than with Michelle. That was kind of embarrassing since I had waited a year to get with her.

My memory is that we each came that night. After we cleaned up and got dressed, Michelle and the friend called a cab and left.

The next Saturday, I went back to Badlands where I saw Michelle and her friend from the threesome. She admitted that she was VERY drunk that night. Our relationship was now back to the usual chatting, flirting, meeting her friends and some dancing.

Of course I kept calling and texting her trying to get a repeat performance. "Please Michelle! At least let me take you out to dinner!"

No dice!

It turns out Michelle was married to a middle-aged man who didn't mind her going out dressed up with her friends. The husband was the original one who was in to dressing up and got Michelle in to dressing up also. That must have been the reason Michelle would not go out with me.

About six months after our original threesome, I ran into Michelle in the Castro with her husband. The husband was also dressed up. Although middle-aged, the husband was dressed up in a red spandex kind-of dominatrix outfit. It was sexy enough for me to think about asking for another threesome.

I didn't.

After that night, I realized there was never going to be any dating with Michelle and probably never any sex either. I was now able to emotionally release from wanting to pursue Michelle.

Oh, and the relationship with the GG flamed out also. That is another story.