The Night I Lost My Cherry Ass

The first time I had a guy fuck me in the ass was when I was very young, just a year of so after I got out of high school. I had just returned from military basic training and married my first wife. I got a part-time job chauffeuring a businessman around who had lost his drivers license. Since his business was selling freezer plans to consumers, most of his appointments were at night.

One night after his last appointment, (his name was Scottie), he said, "I'm really horny - How would you like to get a blowjob?" Being young, naive and stupid, I replied, "Do you know a woman who'll do that?"

"Well, if someone wants to suck your cock, does it matter if it's a woman or not?" he asked?

Not wanting to appear even stupider than I was, I said, "No, I guess not. How do we go about it?"

He told me to drive to one of the city's parks and stop near the "Greek" theater (I kid you not - that's REALLY what its called!). He said if we just waited there for awhile, some "queer" (his word, not mine [smile]) would come to the car and offer to suck us off.

I wasn't too sure about this at all, but I certainly couldn't chicken out now. So we waited and waited... A couple of guys did come up to the car and talk for a bit. But they were looking for the same thing WE were - someone to suck our hard cocks.

After hanging around for an hour of so without "scoring", Scottie said we might as well leave since it didn't look like there was much action going on.

On the one hand, I was somewhat relieved that "nothing had happened", but on the other hand, the "anticipation" had made ME horny as hell too.

Scottie lived quite a ways out of town and as we were headed towards his house he said, "Well, we didn't have any luck at the park, but I'm STILL horny!" And with that, he reached over and started stroking my rapidly hardening cock through my trousers. "And it feels like we're in the same condition," he laughed. "What say we 'take care' of each other? Take a left at the next road and drive down to the end. It's pretty secluded there and nobody's apt to bother us."

"OH, shit!" I thought... "What the hell do I do now? It's ONE thing to have some strange guy suck MY cock but I've never done anything like that - and I don't know if I even WANT to... Shit! I'm scared!!!"

But I'd gone too far to back out now, and as I turned down the dark, lonely trail, Scottie opened the front of his pants, took my free hand and placed it on his hard cock. "Do you like the feel of that?" he asked, as he continued to stroke my hard on. I had to admit to myself that, "Yes, indeed... I DID like the feel of his hard prick" and I slowly slipped my hand up and down his shaft as I drove down the road with one hand. His hand stroking my hard cock felt damn good too.

Scottie's car was a full size station wagon with the back seats folded down and a mattress covering the entire floor. As I pulled the car to a stop and turned off the engine and lights, Scottie said, "Why don't we crawl in the back and get comfortable?"

It was a warm spring night and we both slipped out of our pants and shorts as we climbed into the back of the car and laid down facing each other. After we had played with each other's cocks and balls for awhile, Scottie turned around and taking my cock into his mouth, began deep throating me and squeezing my cum filled balls. Taking my prick out of his mouth for a moment, he said, "Hey, you don't need to be bashful. Go ahead... Give it try! See if you don't like sucking cock as much as I do." Well, his stiff rod was right there in front of my face, begging to be licked and sucked. "Oh, well," I thought. "In for a penny, in for a pound," and I started giving Scottie's cock the same treatment he was giving mine. "Damn," I thought. "This ain't half bad. I LIKE it!!! I then began sucking his cock as enthusiastically as he was sucking mine. As Scottie was sucking my cock and licking my balls, he slipped first one, then two fingers into my puckered (and virgin) asshole. I had NEVER felt anything like that before – It was FANTASTIC!!!

Needless to say, it didn't take very much of that before we were both cumming and shooting gobs of jism down each other's throats. Being a complete novice at the art of cocksucking, I choked, gagged and sputtered as his hot cum hit the back of my throat. And even though I swallowed as much and as fast as I could, quite a bit of his spunk dribbled down my chin and coated his spit slicked balls. (As far as I know, Scottie had no such difficulties and neatly swallowed all I had to offer...)

After we had come down from our mutual orgasms a bit, Scottie said, "Goddamn, kid! You may be a 'virgin' at this cocksucking game, but you've got one hellova' hot mouth and tongue! That was great!"

As we lay there facing each other and resting up a bit as we gently licked each other's cocks, Scottie said, "You know? As much as you obviously enjoyed that, I think you might be ready for another 'virgin treat'. Turn over on your stomach and raise up on you knees."

Well, the truth was, I HAD enjoyed the mutual suck off, and was surprised to see that I was still pretty damn horny and wondering what he was going to try next. I didn't have long to wait as Scottie began to lick up and down between my ass cheeks and run his tongue around and around my asshole, giving me my first ever "rim job." "Oh, man," I groaned. "That feels even better than your fingers did."

"You ain't felt NOTHING yet," chuckled Scottie, as he ran the head of his dick up and down through my ass crack. I thought I was going to scream though when he began to push the bulbous head of his cock into my spassaming and contracting sphincter. At first it hurt like hell and I told him to stop – I didn't WANT that! He told me to just relax as much as I could and that it wouldn't hurt very much or for very long.

As he said that, he reached around and took my now hard again cock into his fist and began to stroke it up and down the full length of my shaft. As I concentrated on those sensations, I did begin to relax a bit as Scottie just left the head of his prick in my ass and didn't try to move or go any further into my previously virgin hole.

Slowly and gently, he started pushing his hot meat deeper and deeper into my rectum. It still hurt a bit and I had never felt so FULL in my life. But as he slowly began to push his cock in and out of my ass, I soon realized that, indeed, it DIDN'T hurt so much anymore... In fact it started to feel damn GOOD! Especially as he squeezed my balls and rapidly jerked me off as he picked up the speed of his fucking my asshole. And as he shot another burning load of cum up my ass, I shot my wad all over his nice clean car mattress.

Again, we rested and talked about what had just happened to me. "Did you like it?" he asked. "Didn't hurt too much did it?"

"No it didn't," I admitted. "In fact, I'm really surprised that I enjoyed it as much as I did! I've never even dreamed of doing something like that. I thought only queers liked that kind of stuff. And I'm sure my wife would tell you that I'm definitely NOT queer!!!"

Scottie laughed at that and said, "No, I don't think you're a queer. I think you're probably a lot like me. If it feels good, it really doesn't matter a tinker's damn whether it's with a man or a woman. Wouldn't you agree?" I had to admit that I did – wholeheartedly!

"Well then, me bucko, it's YOUR turn. I haven't been fucked in the ass in ages." And with that, he straddled my legs and settled himself down on my thoroughly abused manhood and began to fuck himself silly with my cock. And it wasn't long before I came for the 3rd time that night...

As we slipped back into our clothes and climbed into the front seat to leave, Scottie said, "You know, I love getting it on with a guy now and then. But I REALLY like doing it in a threesome with my wife. I just know she'd be thrilled with that young, gorgeous cock of yours. Whatta ya think, Could you get into that?"

"In a fucking heartbeat," I replied... "And my new bride might just be interested too!"

But that's another story...