At 18 my first real girlfriend was Sammie. She had been dating a guy I knew but he dumped her less than a week before a dance. She asked me if I would take her because she had no date. It started as a date of convenience but we continued to date after that for real.
Sammie was cool. She read Penthouse, and shared with me that she masturbated, and we engaged in a lot of heavy petting. I felt up her boobs, and fingered her, and hoped it would progress to handjobs then blowjobs. We broke up first. (Sammie, if you are out there, just know it wasn't you. I was immature)
I had a few first dates after that but they all fizzled.
Then I met Andrea. I dated her longer. She was smokin hot but insecure. We fooled around quite a bit. I always hoped for more just touching but anything sexual made her nervous.
I went through another string of fizzled relationships before dating Diane. To my surprise and amazement she blew me in the front seat of my Cutlass. It was our first date and I was so nervous I almost couldn't cum. We only dated for a few weeks because I couldn't handle her being bipolar. But she blew me on every date. That was fantastic!
After her came Karen then Jamie then my wife. All the girls were so different, but what was always the same was the excitement of a new relationship and the uncertainty of what sexual activity would or would not happen. Of course, generous amounts of alcohol and treating girls like a lady helped tilt the balance.
After being married for about fifteen years I missed that thrill. I tried Craigslist only to discover that there really were no woman on there. There were however, a lot of married bi guys. Heck, a blowjob is a blowjob. So I placed and answered ads with some success. I discovered that if my ads were clever and sexy I got better results.
One time I placed an ad seeking the excitement of a first date. I knew I could just answer some ad from a guy who wanted to blow me, but that wasn't enough. I wanted the outcome to be uncertain like those first dates. I imagined him sitting on the edge of his couch reluctantly blowing me while I stood in front of him. So I placed an ad specifically looking for a married guy who wasn't sure if he wanted to take the next step. I wrote: "Are you intrigued by m2m blowjobs but not ready to take the plunge? Let's watch some porn then you sit down and we will see what happens."
I found a guy who fit the bill and we traded e-mails for a few weeks while he got his courage up. We talked about my need to recapture the excitement of first dates and I shared with Jim what I already told you. We both agreed that we were uncertain about what would or would not happen and that we had to wait to see how the "date" went.
On the big night I shaved my pubes and washed really well in preparation. I don't like getting BJs from guys with beards so I asked him if he was clean shaven and he assured me that he was.
We met at a neutral place to have a drink and check each other out first. It turned out that Jim was a cool guy. He bought us a few rounds and even treated me to an appetizer. He was easy going and I felt relaxed and at ease with Jim. I tried to steer the conversation toward sex like I would do with any girl I wanted to seduce and Jim took the bait. I couldn't tell if he intended to suck me off or not based on the things he said. I mean, he would say coy things about oral sex but they were never clearly an admission that he was willing to kneel for me. He called me Honey or Babe just like I had told him that my girlfriends and I used to call each other. The suspense was really building causing all those old jitters to play on my nerves. It was a perfect date!
I figured by the end of the night we would have to put our cards on the table and head back to his house for a BJ, or not. I dropped hints and waited for Jim to say he wanted my dick but he never said it. Just when I was ready to call it a night Jim noticed that I was too tipsy to drive and suggested that I come back to his house for some rocket coffee which he assured me would sober us up quickly.
All the way to his house I wondered what would happen and realized that he was a master of the game. Again, a perfect "date".
We both sat on the couch with our coffee. I sipped slowly waiting for the right moment to make my move just like the old days. If I put my arm on the back of the couch he put his arm up on top of mine. If I touched his knee he touched mine. If I was reading the signs right I would be standing in front of him feeding him my dick pretty soon.
Should I just ask if he was ready? Maybe I should touch his dick through his pants? Command him to blow me?
I drank some more coffee biding my time which I had plenty of because I was no where near sober. I guess Jim held his liquor better because while I was slurring my words and having trouble balancing I saw no signs of inebriation on his part.
Jim turned on Netflix for awhile then switched it to a porno. Being as tired and wasted as I was I wasn't much of a conversationalist so we mostly watched the girl in the movie being roughly taken by three big-cocked dudes. She had a mouth-watering pussy and I licked my lips several times and commented on how hot it was to see the huge cocks ramming her.
I must have started to nod off. I remember opening my eyes once to discover that my head was on Jim's shoulder. I'm pretty sure his hand was in his pants which was fine by me cause the night was probably ruined and if he jerked off at least one if us would get release.
