With all the recent attention concerning the twentieth anniversary of Woodstock, I couldn’t help doing some reminiscing of my own, especially of the wild sex I had back in the crazy days of the Sixties. I was an enthusiastic promoter of free love and participated in many group gropes and drugged out orgies. My favorite memory, however, is of when a couple of rock ‘n’ rollers popped my anal cherry.
It was a few months after Woodstock, and music festivals were all the rage. I attended one not far from where I lived and grooved to the tunes while high on grass. After the concert I weaseled my way backstage to meet the guys from my favorite group, a band that had a faithful following then but has since receded into obscurity.
Tom, the lead singer, took a liking to me right away when I pulled up my shirt and asked him to autograph one of my tits. He happily obliged. I didn’t look much different from any other hippie girl of that era: skinny as a rail, long red hair straight down to my ass, the requisite dusty blue jeans and tie dyed t shirt but Tom accurately sensed that I was a live wire. “You look like you could suck the chrome off a tail pipe,” he said with a wink.
“That’s right,” I said. “You got a pipe that needs sucking?”
He offered me a joint and asked me to accompany him back to the hotel. I joined him on the band’s bus, where he introduced me to the drummer, Barry. While Tom had boyish, all American good looks, Barr was a brooding, prematurely gray haired fellow who didn’t say much. I would learn later that his actions spoke much louder than words.
Once back in his hotel room, Tom wasted little time getting us both naked and in the sack. He laid me down on my back and straddled my chest, thrusting his cock in my face. I gobbled him up, his bloated balls bouncing off my chin, his shaft slamming down my throat. After a few minutes he pulled out and shot wads of come all over my face. He then sat back and smoked a joint. I remained on the bed, come dribbling down my cheeks. “Hey, why don’t you get yourself off while I watch,” Tom suggested. “I always like to watch a chick play with herself.”
Sounded like a great idea to me, so I scooped up some of the semen on my face with my finger and started rubbing it into my cunt. As I fingered myself to a powerful orgasm, Tom’s cock hardened so it was pointing straight up out of his lap. He was slowly jerking off, his eyes riveted to my sopping cunt.
“That looks pretty good,” he said, rising out of the chair. “I think I’ll have a taste.” With that, Tom hopped back into bed and began feasting on my pussy. He was able to stick his tongue far up my hole, scouring my sugary walls for every drop of nectar he could get. I came again and was so lost in ecstasy that I didn’t realize he was paying special attention to my asshole.
“You’ve got a beautiful asshole,” he told me. I’d never received a compliment on that part of my anatomy before and was pleasantly surprised. Before I could reply, Tom had stuck his index finger, coated with my juices, all the way into my rectum. He twirled it around a bit and laughed. “You’re real tight. Have you ever been fucked in the ass?”
“No, I haven’t,” I said. Having his finger up my butt felt really strange, but it also turned me on.
“Well, what do you say? Let’s give it a try.” Tom then rolled me over onto my stomach and pulled me up by the hips so that I was in a crouch. He stuck several fingers in my pussy to retrieve some liquid. Using my secretions, he coated my asshole and his cock and then slowly sank into my upturned behind.
I can still recall the feeling twenty years later it was so mind bending, so intense, so fucking dirty! I held my breath as his cock inched its way past the tight ring of my sphincter. By the time he was in as far as he could go, I was seeing stars. I felt like one of those guys who can hold their hands over a flame and not flinch. I didn’t mind the pain in fact, I turned it around and combined it with the pleasure I felt, doubling the intensity of this wicked penetration.
I must have been moaning up a storm, because Tom said, “You really did this, huh, baby? Well, I’ll ream you real good.” And he did, pounding into my back door with vigor until he pulled out and squirted all over my ass. He got up to wash himself off. I could only lie there, my face in the pillow, too stunned to move.
Perhaps a minute or two later, I heard the door open and looked up to see Barry enter the room. He was completely nonplussed to see me lying on the bed, my ass in the air and covered with semen, and said a soft hell. “Is Tom around?” he asked. “It’s really dead in this hotel.”
Tom then came out of the bathroom. “Hey, Barry, Pam loves it up the ass. She’s a real screamer, too. Why don’t you slip her your bone?”
Barry gave me a look that said, “How about it?” I looked back up at him and said, “Go ahead, Barry. Stuff my ass.”
Barry stripped and stuck his cock in my mouth, and I sucked him to hardness. His cock was bigger than Tom’s by about two inches, and much fatter. I nearly fainted thinking about how it was going to feel tucked up my back hole.
Once he was fully erect, he lay back, lubricated his cock and instructed me to sit on it. I climbed aboard him and slowly lowered my ass onto his cock. He held it upright and guided it into my asshole, which had been widened by Tom’s cock but not enough to allow an easy entry by Barry.
I felt as if I were being split in two. The initial pain was excruciating, but then, after a little movement, the pain subsided and was replaced by a wonderful feeling of total fullness. I started a mild pumping motion, rising and falling on that mighty cock, reveling in the deliciously dirty sensations. Barry reached up and grabbed my tits, pinching the nipples. I lost it soon after that, dissolving in a wild orgasm that had me throwing my head back and moaning loudly.
At this point Tom stepped up on the bed and offered me his erection. I eagerly sucked him, wishing I could see a film of myself with one cock in my asshole, another in my mouth. Tom was so excited he came in no time, spraying come all over my face again. Barry came a few minutes later, shooting his come deep inside me. I crawled off him and lay down limp as a rag doll.
Since that fateful day in 1969, I have enjoyed anal sex as a regular part of my lovemaking. I’m married now to a very adventurous man, and every month or so I surprise him by asking him to fuck my butt like he owns it. And now, with Sixties nostalgia so heavy in the air, I can’t help thinking back to those boys in the band, who turned me on to the wicked pleasure of ass fucking.
Ms. P.D., California