My girlfriend Jan and I had been together for about five months. It was a relationship I wasn't all that enthused about being in, but it was OK for me at that time. Basically, I was getting pussy on the regular and didn't have that much invested emotionally.
Let me give you a little bit of back story.
She was six years older than me. Despite not being a classic beauty, Jan walked around as if she was the hottest thing on the planet. She often dressed like an 18-year-old rather than the 40-year-old woman she was. Don't get me wrong, she was an attractive woman but she wasn't all she thought she was. She was fairly pale, a 5-foot-6 freckled redhead with shapely legs and a real onion for a butt. Jan loved going to the gym. She didn't have big breasts, but I was more of an ass man anyway.
Me, I'm a 34-year-old black man with an average build. I keep myself in shape by riding my bicycle and long walks. I'm not a gym rat, so I'm not a muscular guy, but I'm satisfied with my physique.
We had met at a friend's Fourth of July party a few months earlier and seemed to hit it off pretty well.
We had dated for a few weeks. Though we hadn't slept together at the time, things seemed to be going well before she suddenly broke things off. Jan left a message on my phone telling me how she had a boy toy she was unwilling to give up and that she also was seeing a sugar daddy who could support the type of lifestyle she wanted.
I thought simply leaving a message was a bullshit way to end things, but like I said, I wasn't emotionally invested. I didn't even call to ask for more of an explanation. I simply just let it go.
One night I walked into my favorite hangout to hear my friend's band play. And there Jan was, sitting with a guy named Clarence, another black man whom I'd known for a long time. I walked over to their table, said hello and chuckled as I walked away.
I genuinely felt nothing and didn't give either a second thought. I danced with several other women that night and ended up having a one-night stand with a woman named Denise, but that's another story.
Anyway, two days later I got a call from Jan. My initial thought was to simply hang up on her but I decided to hear her out. She was apologetic about the way she ended things, and told me that she'd broken up with both her boy toy and sugar daddy.
"So, what does any of this have to do with me?" I asked.
She told me how much she enjoyed our short time together and realized we had a chance for something real and wanted to try again. Because she was on the other end of the phone, she couldn't see me roll my eyes. I let her know I wasn't interested. When she asked why, I reiterated she a boy toy and a sugar daddy, which puts me in third place. And I'm not anyone's third choice, then I ended the call.
Jan, however, was persistent and kept pursuing me for the next three weeks. Finally, I agreed to go on one date with her. We wound up having a good time on the date and had a rousing night of sex. And we continued to date and have sex.
One night were lying in bed one night and she was lamenting how one of her friends, Nancy, was so depressed and lonely. Nancy had broken up with her boyfriend more than a year ago and had not been with a man since. And for some reason, no man had shown any interest in her, which was odd because though she wasn't drop dead gorgeous, she was attractive.
"Dan, do you have any single friends who might be interested in going out with Nancy?" Jan asked.
"I know a couple of guys," I said. "It depends on what she wants. If she's looking for a relationship, I could set her up with my friend Mitch. If she just wants her brains fucked out, I'll hook her up with my friend Tory."
She asked about each guy. I told her Mitch was a nice guy, average looking...not too outgoing but a solid guy. I told her Tory wasn't exactly a one-woman man, to say the least. I mentioned that Tory was into the swinging lifestyle.
The swinging lifestyle seemed to pique her interest in Tory. She peppered me with questions about him, such as his build, his age, where he hangs out. She asked if I ever participated in any swinging with him, and I was honest and told her I did a couple of threesomes with him. Finally, she asked the question I knew was coming, which was about the size of his equipment. All I said was he's not small at all and left it at that as I rolled over to try to sleep.
About 10 minutes later, Jan cuddled up to me, began fondling me and asked exactly how big Tory is. I said I've never measured his cock, so I wouldn't know.
