The events in this story happened in late 1998 when I was 25 but the backstory starts earlier.
I was Pinole Valley High School (PVHS) Class of 1990. Most people don't have a clue what that means, but Billie Joe Armstrong and Mike Dirnt of Green Day were also PVHS Class of 1990. Billy Joe didn't graduate, but Mike Dirnt did in case the band thing didn't work out. Gino Toretta who got the Heisman Trophy in 1992 also went to PVHS but was a Senior when I was a Sophomore.
When I was Sophomore, there was a girl I was attracted to but who wouldn't give me the time of day. That wasn't unusual, there were many girls I was attracted to who wouldn't give me the time of day. When Green Day's "Nice Guys Finish Last" came out, all of my PVHS friends joked that the song had written about me. I was the nice guy that the girls just didn't think had anything to offer.
Sexually, I was a very late bloomer. I'd always been attracted to girls several years older than I was, but they were usually attracted to guys several years older than they were. In 1998 at 25, I was still a virgin except for three blow jobs I had received from street prostitutes in San Francisco. I was a fan of a strip club there called "The Hungry I" which I liked because it wasn't ever crowded and the bartender was cool, and on three occasions I did seek street hookers after I had been there. I had never been with a girl I hadn't paid to be with.
In 1998, I went into a dive bar called "The Capri Club" in El Sobrante. A lot of bikers went to that bar, occasionally a few people from the Richmond, CA charter of the Hell's Angels were there but mostly it was bikers not associated with a club. I was not a biker but I lived walking distance from the bar, so if I went there, I could just walk home and not drive while intoxicated.
One Friday night while there, I sat down at the bar and had a nice conversation with another man and a woman about bands from the late 1960s and early 70s such as Janis Joplin, the Grateful Dead, etc. We had not met each other before, or so I thought. She was clearly a couple of years older than me, and the other guy in the conversation was clearly a couple of years older than she was. Story of my life, I didn't even try to come on to her because I figured if she was going home with anyone, it was him, so I just enjoyed the conversation while I was allowed to. I didn't even buy her any drinks, he did.
As closing time came around, he popped the question to her, telling her, "I usually don't pick up women at bars, but I really enjoyed our conversation, and would like to take you home."
She rejected him, saying, "I can't, my mom is with my kid and I have to get home."
He told her he understood and then he left. As soon as he walked out the door, she turned to me and said, "My kid is at my mom's house. Come home with me."
Holy fucking shit. I was in seventh heaven. I didn't even come on to her, I didn't even buy her any drinks, but she chose ME.
I'm a slow drinker and I don't drink hard liquor, it typically takes me thirty minutes to finish a beer. My guess is I was over the legal limit, but I wasn't drunk. She gave me the keys to her car, and I drove to her place. First we stopped at a 24-hour supermarket to get condoms but the condoms were in the pharmacy area that was closed off at night, so we decided (much to my disappointment) that we would only have oral sex. If we had thought ahead, there was a condom machine at the bar, but when we left the bar we thought we could pick them up cheaper at the supermarket.
When we got to her apartment, she told me to wait in her living room while she 'prepared herself'. As I looked around at her pictures, she had her Senior Prom picture on the wall, and that's when I recognized her. She was one of the Seniors during my Sophomore year that rolled her eyes and totally ignored me when I tried to make conversation, making it quite obvious that I wasn't going to get anywhere.
She came out of the bathroom wearing nothing but a pink camisole. She lifted up the front to reveal her freshly shaved pussy and said, "I'm ready".
I didn't tell her this, but while I had seen plenty of fully shaved pussies at 'The Hungry I' I was actually more partial to some hair down there. Now, I don't really give a fuck, but back then I did. However, I was still willing to eat it.
She grabbed a bottle of alcohol, held it up, and told me, "No offense, but I don't like the taste of spunk," and my cock literally twitched. She didn't like the taste, but she was prepared to do it anyway, I was going to get my dick sucked. She then led me into her bedroom.
I wanted to get down on my knees and bury my face in her pussy, but she dropped to her knees first and started to undo my pants. When she had my cock out, she looked up at me and smiled and started to tease my taint with her middle finger while her other fingers massaged my balls. My cock was now rising to full attention.
She then took my cock into her mouth. The blowjob she gave wasn't like the blowjobs I had paid for, or even like the blowjobs I had seen when I rented porn videos.
She started by kissing the tip of my cock, then swirling her tongue around the head, and then she took it all in---but unlike my previous street hooker blowjobs or porn blowjobs, she made a point of never using her hands. She took my cock all the way in, deeper than I can currently can do on a strapon without gagging, and when she needed to pause to breathe she gently held the top of the shaft between her teeth and trilled the head with her tongue while making a sound similar to a trilled 'R' in Spanish.
My best friend's girlfriend, a waitress whom I will call 'Judy' (not her real name), knew that I had never had sex outside of a few blowjobs with street hookers. She had told me that when I did find a woman, it was very important to try to let her come first: to not be a 'Rocket Man'. Well, despite my lack of experience I did have stamina because of anxiety, but the woman I was with wasn't going to come while on her knees sucking me off, so I asked her if she wanted to move it to the bed so we could 69.
She said, "Sure, or you can stick it in my ass, just not my pussy without a condom."
I didn't want to stick it in her ass. I have fantasies about taking it that way with a strap-on, but personally when it comes to anal, I prefer to receive than to give. So we moved it to the bed and started to 69.
Unfortunately I don't believe I actually got her to come despite my best efforts, it was my first time eating pussy. However, I did get my tongue in there and my fingers in there and I know I got her wet and let me tell you, she had a sweet tasting pussy! It reminded me of freshly picked apples right off the tree, at the perfect ripeness you just do not get from the grocery store.
She continued her amazing technique while sucking my cock, only using her hands to tease my balls and my taint. I can't say I get a lot of blowjobs but I've had numerous since then, and none of them compare to the magic of her technique. If I ever find a domme who likes to watch me blow other guys, I hope to master that same technique she used because just over twenty-five years later, I still think about that incredible blowjob. It's a good technique.
I may not have brought her to orgasm, but sure enough, she brought me to orgasm. She took my load in her mouth, swallowed it, grabbed her bottle of alcohol and then washed it down. After that, she put a Belinda Carlisle CD in her CD player and we snuggled and went to sleep.
In the morning, she told me, "I didn't want to tell you before, but I'm married. I still love him, and my son needs his father. He is getting paroled from San Quentin next week, this was just my last fling before he gets out."
I told her I understood. She wasn't the right woman to have a relationship with anyway, she was way too submissive. I did however learn that submissive men like myself shouldn't avoid submissive women, we can learn a lot from them!
I left her apartment on cloud nine and walked to Zip's, the restaurant where 'Judy' worked. She was there for the morning shift. I told her to smell my fingers. She gave me a weird look and asked, "Why?" to which I replied, "Just do it."
She did, and then her eyes opened wide and she said, "Oh my God, you finally got laid!"
I didn't tell her it was only oral.
My dick still hadn't had pussy, but my tongue and fingers sure did! This nice guy finally got to finish.
