All people in this story are 18 or over
James Porter was tired of being a virgin. Here he was a grown man -- twenty-four -- and the closest he ever got to getting laid was feeling up Valerie Martino. But Valerie came from a strict Catholic family and she was adamant that she would not have sex until she was married. She'd even signed a parish-sponsored purity pact with God, which James, who was also raised Catholic, thought was ludicrous.
Valerie moved away to go to college. James never found out which one. She never said goodbye; one day she was there, the next she wasn't. Her parents always hung up on him when he called her home. The last time, her father threatened to have him arrested. He never called the Martino home again.
James didn't think he was bad looking. He'd measured his erect penis several times. A little over seven inches. He showered daily, wore deodorant, and sometimes wore cologne. He had a good job and wore nice clothes. He implored an attractive (but unfortunately married) female co-worker to bluntly tell him, as a woman, if she saw anything wrong with him.
"Nothing as far as I can tell," she said confused.
What the fuck is wrong with me? he thought.
He had grown tired of masturbating to Internet porn. Then he came across Literotica.com. James was stunned.
These are ordinary people writing sex stories and getting published online for the world to see!
He became an avid reader of the site. He fantasized himself in raunchy adventure after raunchy adventure as he masturbated to orgasm.
Then he came up with a plan.
Wait a sec! There has to be thousands of female members around the country. This is Chicago. There has to be at least one horny woman in this fucking city on the site who is willing.
Later that night, he decided on a plan. He would write a story about his frustrations. He would create a fictional character which was him. He registered at the website, and for five days, he wrote and rewrote and rewrote. Every one of his sexual frustrations were poured into the six-page story. Once a volunteer editor proofread it and her suggestions were implemented, he submitted it. The lady even gave him words of encouragement, adding that if the pic he'd sent her was real, she'd gladly "pop his man cherry" and extended an invitation for him to "cum down south."
"I don't have the money to fly up there," she said. "It sucks because I'd love to cum to/for you."
A few days later, the sad story of William Adams of Chicago went up on the Literotica site. And although he was not religious anymore, he prayed.
After two days, he'd gotten a few positive comments on his story and his writing ability. But they were from guys saying they could sympathize with William. Then a poster sent him a private message. And it was a woman! ChicagoVixenV was her username. She said she loved the story! He thanked her in his reply.
Then he got another private message.
In many ways, my frustrations were worse than yours. I won't go into details yet.
I was a virgin until I was nineteen. I saved myself for marriage. Then I got married. And within six months, I found that the bastard I'd saved myself for was cheating on me! I dumped him and I got the marriage annulled. As soon as it was official, I whored out like crazy for over two years. I love all kinds of sex, but now I'm responsible with it.
If being a virgin is your problem, I'd like to help you. But I think that's just the tip of the iceberg. And I think I can help there, too.
I'm serious... "William." In confidence, I'm giving you my cell phone number. Call me.
James was stunned, but wary. Why did she put his false name in quotes? He held his iPhone and stared at it for over three minutes like it would answer back to him.
Oh, to hell with it! No risk, no reward, he thought as he nervously dialed the number. A sexy-sounding female voice answered.
"H-hello, is this ChicagoVixenV?" he asked.
"William?" said the voice after a few seconds of hesitation.
James suddenly felt... Uneasy? No, that wasn't it. Something was... He couldn't think of the appropriate word.
"Y-yeah. Actually, it's James."
"Call me Val. Everyone does," she said.
"Okay... Val," replied James. "Is this on the up-and-up?"
"Yes, James," said the mystery woman. "Entirely."
"Why?" he asked.
"There are several reasons. I'll let you know one right now: because I want to." she said.
"And what're the others?" he urged.
"You'll see. Now, do you know where Holiday Inn Midway is?" she asked.
"Y-yes," he said.
"Good. Get over here," she said firmly.
"Wait! Y-you're there? Val, are you a..."
"Prostitute?" the voice on the other end of the phone sighed and hesitated. "No. There will be no money changing hands, James."
"Sorry, Val. I-I-I..." he stuttered.
"It's alright, James. Just calm down. I know all of this sounds bizarre. But there's a reason for it," she said. "Give your name -- your real name -- at the desk and ask for the key to room 335. They'll know they can give it to you. Just calm down and drive safely."
He sighed. "Okay. I'll see you shortly, Val," he said with a dry mouth.
"See you soon, my love," said Val, her voice becoming strangely emotional emotional again. Before he hung up, James could have sworn he could've heard crying.
En route to the hotel, he was certain this was a trap of some kind. But what if it wasn't? He arrived at the hotel within a half hour. James was still suspicious, but the lady at the desk immediately gave him the key and cheerily exhorted him to enjoy his stay with them.
That remains to be seen, he said to himself. He thanked her.
He rode the elevator up to the third floor and found room 335. He closed his eyes took a shuddering deep breath and knocked.
"Come in, James," said the voice from behind the door. He opened it. The lights were off, but he could see her standing in silhouette against the window. She was backlit by Chicago's bright lights streaming through it. Although he could not see her face, her figure was clearly accented. He felt his penis hardening.
"Thank you for coming, James," the woman said. "I've been wanting this for a very long time. Over five years, in fact."
"Five years?" asked James in confusion. "W-who..."
"Yes," she said. "Five years. And I'm sorry for what happened. When I read your Literotica story, it sounded familiar. And so here we are. I understand your sexual frustrations. If I didn't..."
He interrupted. "Have we met?" A confused look was on his face. He could not shake the feeling that he had heard her voice somewhere before tonight.
He heard the woman choke back tears
"Do we know each other?" James demanded in a louder, firm voice.
"Yes, James. We do," she said. And she walked to the wall and raised the lights. James' eyes went wide. And suddenly, the mystery was solved.
"Valerie?" he said. "Oh my God!"
She nodded. She'd been crying.
"Oh my God!" he repeated. "You look incredible!" he gushed.
"Thank you," said Valerie. "And you're still as handsome as ever." Tears began pouring down her face.
"Hey... No," said James. He walked to her and they hugged. Valerie sobbed.
"Don't cry, Valerie. What happened?" he asked.
She sniffed back tears and after a minute of trying to compose herself, she began explaining.
"I was brainwashed by priests and nuns and... I don't know... sexually ignorant people. My father sent me away to a private all-girls' college out west. He heard about us. He was always possessive. Mother finally divorced him about a year later. He said I had to go to the school or I was dead to him. Anyway, I left the school after I was almost raped -- by another girl of all things. I called my father. He didn't believe it and he accused me of being a whore and disowned me. We haven't spoken since."
"How'd you make a living?" James asked.
Valerie hesitated. "Anyway I could," she said. "But that's my burden. I wanted you, James, but..." She shook her head.
James tearfully held her hands. "I still love you, Valerie. I've never stopped loving you. And whatever happened to you, I'll still love you. Just stop living in the past."
They hugged again and cried for ten minutes.
"So, do you still want me?" Valerie finally asked.
"Yes," said James. "With all my heart. You're the only woman I've ever loved."
They tore off each other's clothing and were nude in minutes.
"Okay, James," said Valerie. "Time for you to go to school. You're going to learn to make love, not just fuck. You'll find I'm a very sexually -- charged -- woman."
Valerie pulled James to the bed and pushed him down and kneeled in front of him.
"If you cum fast, don't worry about it. It's normal," she said stroking him to erection.
"We have all the time in the world, my love."
And she took his throbbing penis all the way in her mouth. Greg was so shocked he couldn't talk. Within two minutes, he shuddered and roared. His cock erupted, shooting what felt like a gallon of cum down Valerie's throat. She took it all.
"Oh my God, Val! Where...?" he finally asked.
"Lots of places," she said.
After he became hard again, James Porter learned the art of lovemaking under Valerie Martino's experienced tutelage. When he entered her tight vagina, he began crying again. Not out of pain. Not just out of relief. But of gratitude. His Valerie was back. It was a pact. He and his only true love would never be apart again.
The following morning, while Valerie showered, he got on the Internet and found the name he was looking for. and made a phone call. A man answered.
"Hello? Martino residence," he said.
"Mr. Martino?" James began. "My name is James. We have something very important to discuss..."