It's common for people use the analogy of a crossroads to describe times of fundamental choice in their life. Of course, it also describes two roads that happen to cross. For me, on a Saturday morning in the late summer of 1989, both descriptions were apt.
For our younger readers, in 1989, there were no cellphones or Uber, and we all seemed to be perfectly happy with being disconnected from the rest of the world. There were no social media or dating apps and most of us tended to meet girls at the local bar or club on a Friday night. I tell you this because it's relevant to how I ended up standing in front of a Stop sign on a country road, halfway through an 8 mile walk back to my apartment.
I was 22 and had landed my first job out of college with a good-sized regional bank. I was excited and assumed I'd be assigned to one of their main offices, but they believed that new young managers should start work in one of their local branch banks. That's how I ended up in a small town in Oklahoma, assigned as the branches' assistant manager. In and of itself though, that doesn't help explain where I was standing. That was the result of having drank too much, made a bad decision, then corrected that error with what I believed was a smart decision.
I had gone out the night before with a group of friends to one of the so-called nightclubs in town, the Crazy Eight. We had been pounding shots and I found myself on the dancefloor slow-dancing with a girl that had clear designs on taking me home. Normally, that would have been perfect, but for the fact that the Tequilla had seriously swayed my standards.
An hour later, I was in her bed. I'll admit that her body wasn't all that bad, but even in my alcohol-clouded mental state, I knew that fucking her, sans condoms, could very easily lead to me being trapped in this small town with someone I didn't want to be with. Fortunately, one of my college girlfriends had taught me a lot about oral sex and I was able to get her off twice with a combination of my tongue and a couple of well-placed fingers. She tried doing the same for me, but I was drunk enough that I never came.
The next morning, I was jarred awake when her roommate jumped up on the bed and in an overly cheery tone asked, "So, how was it?"
Her roommate was actually modestly cute, with curly hair and what looked like nice, perky tits under a thin, oversized sleep shirt. Rhonda, the girl I had just spent the night with said, "He didn't want to fuck, but he has a seriously talented tongue."
"Ooooo...maybe he should show me," she said, pulling her nightshirt off and exposing her nude body. Her tits where just as perky as I had thought, with puffy, pointed nipples. Before I could look lower though, Rhonda threw a pillow at her.
"You're such a slut! He's my date and you need to go find your own."
"I'm sure he wouldn't mind having both of us...would you?"
"Get the fuck out of my room," Rhonda said in a near yell.
"Whatever." With that, her roommate grabbed her nightshirt, got off the bed and headed out the bedroom door, showing off a seriously cute ass as she pranced away.
I looked over at Rhonda, and my prior night's judgement, while seriously clouded, had been spot on. She was just plain ugly and not even her half-way descent body and clearly liberal attitude about sex could overcome that simple reality.
I made an excuse that I had a bunch of errands to run that day and had to leave. I quickly dressed and turned down an offer of a ride home, claiming it was a nice morning and I would just walk. In truth, I didn't want her to know where I lived. It was only after I had walked a mile and stopped at a convenience store that I realized I was actually on the northeast side of town and lived nearly 8 miles away. Oh well.
It really was a gorgeous morning, and the walk was fairly pleasant, although I was horny as fuck. My big brain kept reminding me I had made the right decision, but my little brain kept chiming in about how fun a threesome would have been...and her roommate's ass has been seriously hot.
The fastest way to get back to my place took me down a long, straight rural road just on the edge of town. I was about halfway home when a car pulled up and asked if I wanted a ride. The driver was an older man in his early 60s and seemed reasonably nice so I accepted the ride. I told him where I was going and he said it was on his way and he'd be glad to drop me off.
He asked me why I was out walking and I gave him an abbreviated version of the previous night. He thought the story was funny as hell and pressed for more details so I went ahead and spilled the details, including about the roommate.
"No real surprise, you're a really good looking guy. That's a lot of willpower though. You must be horny as hell." He said this as he took several glances over at me, including looking down at my crotch. I noticed, but didn't really think anything of it.
"Definitely after all that. I'll probably take a long shower when I get home."
He looked down at my crotch again, then back at the road and casually continued, "Young guys like you have a lot of needs. I used to jack off all the time when I was your age...You like to masturbate?"
What the fuck? Did he really just say that? I was totally unsure of how to respond, but in my seriously horny state, I just answered honestly. "Yah. Who doesn't?"
Very casually, he said, "It's natural for guys to masturbate. I still do every day. Not much pussy when you get to be my age though, but that's their loss. My cock still gets just as hard as always." He paused for several seconds then continued, "You're a lot younger though and in your prime. You probably need to multiple times a day," letting the comment hang in the air.
I have zero idea why, but I answered truthfully again, "Yah, pretty much whenever I can."
He looked down at my crotch again, then back at the road. "You should now. I'm sure you really need to and I won't mind."
At this point, I should probably provide a little background context for how I responded and what I did next. I was a cute, but skinny kid growing up, my body well outpacing my coordination, so sports just weren't really in the cards for me except track, where I ran distance and routinely won. Other than track, my main extracurricular activities were band and theater.
Most of my closest friends were girls and at times, I guess my mannerisms could be a little fem. This led to a fair amount of teasing and being called fag or gay, which I never considered myself. I was raised in a very normal, midwestern, conservative family and the idea of being gay just wasn't an option.
That said, when I went to college, I discovered an adult theater in the city and began going from time to time. Seeing sex on the big screen was something I had never experienced and it made me even hornier, if that was possible. Sometimes, older guys would come sit close to me and take out their cocks and openly stroke. At first, I was way to nervous to do it, but eventually, I tried it and found showing off to be an incredible turn on.
My body was lean and fit. I was 5' 10" and 135 lbs, with green eyes and near shoulder-length dirty blonde hair. Other than normal pubic hair, at least initially, the rest of my body was pretty much smooth. Today, people would refer to me as a twink, and my round, bubble ass certainly added to that definition. I was one of the few young guys that went to the theater so I tended to get a fair amount of attention from the other guys in the theater.
The first time a guy came over and took hold of my cock, I was so shocked, I sat their frozen and let them jack me off. Being the first time, I came in no time and immediately fastened my jeans up and left, very embarrassed by what had just happened.
I couldn't get the experience out of my mind though and started going back, usually a couple of times a week. I found I loved the attention and would let the older guys come sit next to me and stroke my cock and soon I was stroking theirs. Then I got my first blowjob from a guy. Again, I came in no time but hung around a while longer afterwards.
It was around this time that I began dating Samantha, Sam for short. I think she sensed I'd make a fun play toy and it turned out she was right. She wanted to be in control and explore all her desires and was looking for a sub guy to follow her lead. I was more than happy to be just that person.
Sam's the one who taught me all my oral skills. She loved oral sex and could have the most amazing orgasms from it, squirting at least a little almost every time if I did it right and a lot if I managed a particularly good job. Sex was the same way and we always needed a towel under or, or to do it somewhere that it didn't matter if we made a mess.
I totally loved spending as much time between Sam's legs as she wanted. Part of the reason was that she shaved bare, and I never had to deal with getting hair in my mouth. Even though a few porn stars had begun shaving by 1989, it was still uncommon, which made it all the more exotic and sexy. She said it was becoming popular with some lesbians since it facilitated better oral sex and scissoring. She added that it also made cleaning up a lot easier given how wet she got during sex.
Even though the rest of my body was essentially hairless, I had a thick patch of blonde pubic hair, which was a nonstarter for Sam. She used an initial blowjob to explain just what was at stake, then explained that further oral pleasures would require her to deal with "the forest" as she put it. This led to a trimming session with scissors, followed by a long, shared bath. When it was all done, I was as smooth and bare as the day I was born. Fortunately, she also introduced me to Lidocaine gel, which prevented all the bumps associated with new shavers.
I honestly think I was probably one of the very first guys who had a totally shaved pubic area. I was more than happy to do it for Sam as the oral sex was truly amazing and I couldn't help but admit that I really liked the look and feel. To this day, I still keep myself totally bare.
Besides oral sex, Sam also loved to play with toys and had a fetish for fucking me with her dildos. We both quickly discovered my body really responded to that type of sexual stimulation and she ended up buying a strap on, and after that, we traded fucks one for one.
She's the first person to openly and honestly tell me I was gay, but if I enjoyed being with women, there was no reason I couldn't enjoy both sexes equally. This was a revelation to me and something that took time for me to digest as I was pretty naive at this point and really didn't fully understand the concept of being bisexual.
Sam taught me that society puts everyone in a box, but I could choose to be who I wanted and do whatever I enjoyed doing. She explained that she was bi and enjoyed being with men and women equally and believed that we should be able to enjoy our bodies and be with who we wanted to be with. This concept was totally foreign to me, but it made a lot of sense and the more I thought about it, the more I felt like it fit for me.
We continued seeing each other for nearly six months until she graduated and moved to California to start a new life and continue her exploration of desires and experiences. I continued casually dating and enjoyed sex with several more girls, but it never approached the intensity of what I shared with Sam. I was still far too insecure to try dating guys and really didn't know how to meet them other than my continued trips to the adult theater.
Before she left, she gave me a going away gift. I opened the box and found two dildos and a strap on I could use with either. I never met another girl that used the strap on, but continued to routinely use the dildos on myself. I still have the larger one and it always reminds me of Sam whenever I slide it into my ass.
