I was sleeping with this guy, Michael, pretty regularly. He was in a relationship so it worked out great for me. We got along great in every aspect. By this time I was recently divorced & had my own place. My friends would come over regularly & we would hang out & party. Michael would join us on occasion & my friends got along with him. I was hanging out more & more with a friend I met from work, Tracy. She was in her early forties but looked like she was in her late twenties. Petite, beautiful face & really big natural breasts. Tracy worked out daily, was a Vegan & very fit. She loved to party though & smoked daily! Her ex gave her a substantial monthly Alimony payment so money was never an issue & she always had Primo weed! Her manners & demeanor were impeccable & she described her ideal guy as "Clean cut, well dressed, professional, articulate well mannered, tall dark & handsome!"
Michael had a real good friend, Manny, who was a serious ladies man. He wasn't bad looking but his biggest talent, besides his supposedly large penis, was his ability to sweet talk women. Manny had met up with us a few times at different clubs or the beach. He was a bit arrogant but he was fun to be with. One night when Tracy & Michael were both over, Manny calls. Wanted to know what we were doing. We decided to meet up at nearby Hooters for drinks & Chicken wings. We figured that Tracy & Manny would meet & we could all just hang out for the evening. He was not her type in any way shape or form. Once there Manny is immediately attracted to Tracy. She was not. She ordered her usual order of French Fries & extra celery sticks & we had drinks & hanged out. Manny was putting on the charm Extra Thick. By the end of the night they had arranged to go out on a date the next day.Talk about "Shell shock?!?" I had never ever thought she would like this guy.
Next day they go out & Tracy calls me to see if she can come over with Manny. Michael was over as well so I said sure. We smoked & drank some whiskey & they were getting more playful so Michael & I decided to go into my bedroom & give them their privacy & in turn we could also have sex. I take a shower & when I finish Michael was passed out on the bed! Turns out the combo of weed & whiskey messed him up. Talk about a Buzzkill! I put on the TV but I was really horny. So I pull out my Rabbit & begin playing with myself. All of a sudden I hear Tracy repeating over & over "No. No. No!" I grab a robe & open my bedroom door. Manny was buck ass naked & Tracy was only wearing her panties. Manny was soft but his penis seemed average. Turns out &, I KID YOU NOT, the issue was that Tracy is Jewish & Manny was uncircumcised. Tracy had NEVER seen an uncircumcised cock. EVER! I called her over & explained that it's not a big deal at all. Once he gets hard his head will be exposed & it's the same feeling, I told her. Well she was pretty nervous so she pulls out another joint & we smoke some more. I was horny & getting frustrated with her silliness to be honest.
Meantime Manny is sitting naked on the sofa. I ask Manny to stroke himself so he can get hard. This was so surreal! I'm acting like some sort of SEX referee! However the sight of a naked man, on my sofa, while a couple of minutes earlier I was using a vibrator was a bit unsettling. I look over at Tracy & just tell her to figure it out. "What do you want me to do?" I ask her frustrated & annoyed. Manny blurts out "Get me hard!" I look over & he has the biggest silly smile on his face. That bastard! Of course he would like that. Tracy looks over at me & she actually says to me that she would love to see how I get another guy hard. She has never seen anybody have sex in front of her. When Tracy said this I guess my hornyness began rationalizing this as a possibility. I mean Manny had a very nice body & he was after all naked in my living room. "You only live once!" I thought to myself so I grabbed Tracy's arm & walked her over to the sofa. I instructed Manny to stand up & to get right in front of me.