Art in the Back Seat: My Very First Handjob

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The first “dirty little secret” that I ever shared with my live-in boyfriend, Ray (not his real name), was a real doozie! It was about how I had lost my virginity in a very unique way, back when I was a young lady. It happened on a hot and sunny summer Sunday afternoon, when I was unexpectedly cornered in a small bathroom at a middle-aged Hispanic friend’s equally-small house, and then sexually molested–and ultimately raped–by her teenage son, Freddy, who was so dark-skinned that he looked more like a black guy, than a Chicano.

And I didn’t try to run away from Freddy, or scream for help, or fight him in any way. Instead, I ended up cooperating with him throughout our entire sexual encounter, which lasted about 15 to 20 minutes or so. And by the time that Freddy finally left the bathroom that day, I had several strong orgasms under my belt and a sopping-wet pussy to show for it, along with a whole wad of Freddy’s freshly-ejaculated sperm deep inside of my totally-unprotected, previously-virgin vagina. And no. Freddy didn’t get me pregnant that day–thank God!

My sharing of that extremely-intimate, long-kept secret with my “better half” only served to strengthen our bond, and to pull us even closer together than we already had been, up to that point in time. Ray totally accepted me and my unique sexuality. And I totally accepted him and his sexuality too.

After my confession about Freddy, Ray gradually opened up even more to me, as he eventually went on to confess several more of his own “dirty little secrets” to me. All I can say is that there sure were a lot of them. And the more I learned about Ray’s unique sexual experiences during his younger years, the more I was amazed and intrigued by his totally-open and candid sexual attitude.

Then one day, Ray and I were lying naked in bed together, talking and fondling each other’s genitals, as we were getting in the mood to have sex. And I decided that it was finally time for me to share my second “dirty little secret” with Ray.

So, as I was slowly and playfully pulling his foreskin up and down the shaft of his not-yet-erect penis, I said to him, “Remember when I told you all about Freddy, and you told me that it really turned you on to find out that I had actually had another guy’s dick and sperm inside my pussy?”

And the ensuing conversation that took place between us went something like this:

“Yeah, of course I do,” Ray answered me, just lying there on his back at this point, and enjoying my manipulation of his slowly-stiffening penis.

“Well, would it also turn you on if you found out that you’re not the first guy that I ever jacked off?” I asked, waiting to see what Ray’s reaction would be.

“You’re kidding me, right?” Ray said.

“No, I’m not kidding. I really did jack off another guy. It happened right before I met you. So does it turn you on to know that?”

“Oh hell yes! God, you’re just full of surprises, aren’t you?” Ray commented.

“Hey! Look who’s talking,” I replied defensively, and then immediately let go of Ray’s dick, to help make my point. “How many ‘bombshells’ have you dropped on me recently? I wasn’t exactly expecting you to tell me that you had an on-going secret sexual relationship with another boy back in high school, you know?”

“No, you weren’t, were you? So are you trying to get even with me for that one?” Ray asked.

“You bet I am!” I emphatically stated, meaning every word of it.

“So then you actually jacked another guy off, before you ever met me?” Ray asked, still not quite believing what I had just told him.

“Yep,” I calmly replied, nodding my head a couple of times.

“Wow! Were you dating this other guy at the time?”

“Yes, of course I was.”

“Did you let this other guy play with your pussy too?” Ray asked, as he was reaching across into my crotch to start fingering my crack and my clit.

“Yeah. I did,” I answered, realizing that I had hit on something that really turned Ray on, because his dick was now at full-attention, and I hadn’t even touched it since I let go of it earlier.

“You do mean your bare pussy, right?” Ray immediately asked, obviously still trying to wrap his head around what I was telling him.

“Yes. But he was the only other guy that ever touched or played with my bare pussy, besides you.”

“What about Freddy? Doesn’t he count?” Ray asked, catching me totally off-guard.

“Of course he does,” I eventually answered, after an awkward moment of silence, and then quickly added in my own defense, “But that was totally different. Freddy wasn’t my boyfriend. And I didn’t jack him off.”

“Sure you did. You just didn’t do it with your hands. That’s all,” Ray remarked sarcastically.

“Shame on you! You’re so bad!” I said, and then reached across to give Ray a soft-but-quick slap on the shoulder with my open hand.

“Yeah, but that just makes me more lovable, right?” Ray said, with a big forced fake-looking smile on his face, and then asked me, “So who was this ex-boyfriend that you jacked off? Do I know him?”

I slowly nodded my head in response to Ray’s last question. And after hesitating for a few more awkward, silent moments in order to try to figure out the best way for me to break this latest “piece of news” to Ray, I said, “Well, you know that I dated Art for a long time, right before I met you–”

“Oh my God! Art’s the guy you jacked off!” Ray blurted out. “He seemed like real jerk to me!”

Ray knew Art pretty well, because Art was a member of the same college fraternity that Ray had pledged during his first semester at the university, where we were all students together. And Art had pretty much acted as if Ray didn’t even exist, whenever the two of them were in the same room together. But that was primarily because Art still had feelings for me. And he was very jealous of Ray, because I was dating him, instead of Art. By the way, Art’s legal name was Arturo.

“He is. And he was!” I quickly agreed with Ray. “But unfortunately, it took me quite a while to figure that out. And since my mother really liked Art a lot, I tried my best to get things to work out between us. I mean, Art was that light-skinned, upper class Hispanic guy that my mom had always wanted me to have as a boyfriend.”

“So then, unlike Freddy, Art had that light-skinned kind of dick that really turns you on, right?”

“Oh yeah,” I said very softly, but not because I was answering Ray’s question. Instead, it was because I was automatically vocalizing in response to my own mild orgasmic sensations, thanks to Ray’s adept fingering of my clit and my pussy crack, which had just “broken the ice” for me enough to give me my very first orgasm of this particular sexual encounter.

“That’s what I thought,” Ray replied, without missing a beat.

“Okay, okay, you’re right. I admit it. Art’s dick did turn me on much more than Freddy’s did. But not nearly as much as yours does,” I added truthfully–right after I had just finished lying to Ray about Art’s dick turning me on more than Freddy’s did.

I reached over to gently squeeze the firm-but-spongy head of Ray’s dick between my fingertips a few times. And then I started fondling his sexy balls. And I kept on playing with Ray’s balls, and he kept on playing with my pussy, while I went on to tell him my story about Art.

“Anyway, Art and I were going steady, and we had dated for nearly a year. And naturally, we got more and more intimate with each other as the months went by, just like you and I did, back when we were dating.

“Then one night, Art and I finally ended up masturbating each other.