Micropenis

When he pulled off his pants, his micropenis was nestled in his foreskin with the little tip just beginning to peek out. It was so small that he sometimes struggled to hold it to masturbate it. Placing his thumb and forefinger on the foreskin, he moved them forward toward the tip several times, pulling the foreskin over his slit and gently massaging his glans. He took a deep, steadying breath and then repeated this gesture in a steady rhythm for several minutes. Sometimes he moved his index finger up right to the opening of his foreskin so it rubbed against his tip, and the roughness of his finger on his uncircumcised glans caused him to gasp lightly each time.

He truly was a 40-year-old virgin, his tiny penis a carefully guarded secret known only to himself. It had always been plainly obvious to him that his dick was not only abnormal, but also so miniscule it made many sexual activities anatomically impossible. The closest he had ever gotten to sex was purchasing a fleshlight on the Internet ten years ago when he turned thirty. He had been immensely disappointed to find his dick didn't even penetrate past the loose labia into the tight vaginal tunnel, making him unable to bring himself to completion with it.

The last thirty years of his life had therefore consisted of the only method of masturbation available to him, grasping his micropenis between his thumb and forefinger and working himself to completion. He varied it up by changing positions—sometimes lying on his back, other times standing up, and if he was really feeling kinky, on his hands and knees with his ass in the air. He had tried humping and grinding when he was younger, but his tiny penis didn't achieve enough contact with the surface he was trying to masturbate to stimulate him to orgasm. It was a disappointing-to-non-existent sex life.

At his 40th birthday party several months ago, he had gotten impressively drunk and revealed his secret to his best friend. "But you've never even tried it?!," had been his friend's response to the big reveal. And that was why now he was in a seedy motel masturbating as the prostitute his friend had hired for him to "experiment with" lay on the bed watching him carefully prepare himself for the act.

The anatomic impossibility of penetration with his micropenis and the humiliation that would accompany any attempts at sex had always hampered his desire to try. But now, as he masturbated himself and took in the prostitute's splayed legs and glistening, pink pussy, he had to try.

As the prostitute lowered her fingers down to stimulate her clit, he tightened his thumb and forefinger more firmly and began pushing his penis down into his pubis. With just a couple more strokes, he knew he could come.

Desperately, he clambered onto the bed straddled one of the prostitute's legs so that they were in a scissoring position. He ran his fingers down her pussy until he found her entrance, and then lined up his micropenis and thrust forward.

The warm, wet, sticky feeling of her lips surrounding his dick was so good. He was barely able to prevent himself from uncontrollably fucking her, instead holding himself in place for a couple seconds and basking in the brand new sensation.

Then he pulled back and thrust again. Or tried to. His penis bumped against her labia, missing her entrance completely. He found it again with his fingers, lined up, and pushed. He pulled back to thrust again, and found his dick had popped out and was rubbing on her labia once more. He tried the thrusting maneuver several more times unsuccessfully. His dick was just too short for fucking.

The fall-out-then-guide-back-in-with-fingers method was not near enough stimulation for him to orgasm, but her vagina felt so good. Trying to mimic lesbians scissoring, he guided his dick back in and then tried aggressively grinding his hips around. It definitely felt good, but it wasn't going to bring him to completion.

Letting out his first moan of the night—sadly one of frustration and not arousal—he stopped moving and held himself with his micropenis "in" her vagina. His pubis was pressed tight against the prostitute's; if he didn't actively press against her, his penis would come out of her. He tried slipping his hand down and in between their bodies to see if he might be able to masturbate himself while he was inside of her. He had barely wiggled a couple fingers between them when he felt his dick lose contact with her pussy. At this point he accepted what he had originally known and returned to the only option that had ever been available to him.

Grasping his micropenis tightly between his thumb and forefinger, he thrust his hips forward and simultaneously pressed his micropenis back against his pubis with his thumb and forefinger. Sometimes his thrusting caused the very tip of his penis to touch the prostitute's wet, glistening lips, which was both incredibly arousing and also horribly unsatisfying.

His breaths began coming in spurts as he felt himself approach the edge. He leaned over and held himself with one hand as he masturbated himself with the other, trying to move his micropenis as close to the impenetrable pussy as he could. He came in a long, thick spurt as the very tip of his penis touched the prostitute's labia, spilling cum all over the outside of her vulva. Of course not a drop actually made it inside, though.

He continued to hold his penis against her cum-soaked vulva after coming, perhaps for several minutes, before finally pulling away and moving back to put his clothes on.

When he pulled the money his friend had given him out of his pants to pay her, the prostitute just waved him off and said, "No need." He stood there, still a virgin, and watched her leave.