Lenny Loses His Virginity

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Do you mean to tell me that you are twenty-five-years-old and have never fucked a woman?

Jack and Lenny met while taking evening courses at the local community college. Most of their fellow students were in their late teens and early twenties but Jack and Lenny each had already celebrated their twenty-fifth birthday.

After the first evening of class, they visited a nearby coffee shop and talked about their back-to-school-after-seven-years experiences. They talked about having to buy the text, they talked about the professor, and they talked about the beautiful women in their class; especially that “mature, well-built redhead” who sat near them in the back of the crowded classroom. They learned her name was Barbara.

Jack worked in a few not-too-subtle references to his vast sexual experiences.

Lenny innocently said, “I wouldn’t know. I’m not married.”

That’s when Jack asked the embarrassing question. “Do you mean to tell me that you are twenty-five years old and have never fucked a woman?”

“Yup,” Lenny shyly responded.

Jack shook his head in disbelief.

The two men finished their coffee, finished their conversation, and each went his own way.

As he walked to his car, Lenny thought, “I felt foolish telling Jack I never had sex with a woman, but it is true. Jack simply took it for granted that I had sexual experience. I was brought up to think it was wrong to have premarital sex. I assume he was, too.”

As he drove home, Lenny thought, “All those nights and morning when I jerked off on my pillow and I felt guilty as hell. Now, not only Jack thinks I’m queer but my psychology teacher tells me jerking-off is a normal biological function. Virtually all males masturbate one way or another.”

As he continued his drive home, Lenny thought, “All those girls who let me feel their tits. They knew what I was doing, especially when they helped me unsnap their bahis firmaları bras. They knew what I wanted when I went parking with them. And I thought I was some kind of a weird-o with an over-zealous sex drive.

Lenny’s thoughts continued. “I can’t think of one of those girls who stopped me from finger-fucking her after she let me feel her tits. And, every one of them that I finger fucked, lifted up her ass so I could take off her panties.”

He smiled at his memory of Gloria. “Gloria didn’t always lift up her ass. There was that night at the drive-in theatre when she went to the rest room and when she came back, she handed me her panties. ‘I took them off to make it easier for you,’ she said. She knew what I wanted. After that, whenever we went to the drive-in, she put her panties in her pocketbook. I guess I should have fucked her but I didn’t. I jerked off on her stomach.”

At the traffic light, he saw a pedestrian who reminded him of Polly. “Polly had the prettiest tits I ever saw and I have seen a lot of them. She liked it when I finger-fucked her.” he remembered. “She made me come in my pants.”

As he continued his drive home, Lenny thought, “All those times I masturbated against my girlfriends only one of them ever stopped me. And she was the only woman who chased me after we broke up. She still said ‘No’ when I gave her a second chance. Oh, well, I hope she is able to find a man who doesn’t want to jerk off,”

As he continued his drive home, Lenny thought of that blond Carol. “Carol even offered to let me put it in her, but I was afraid she’d get pregnant and I would have to raise our baby plus the two-year-old baby she already had at home.”

Lenny arrived at his apartment.

The following weekend, Lenny took the overweight customer service clerk from the bank to the movies. After the movies, he asked her if she wanted to park at the beach and talk. She agreed. Talking kaçak iddaa led to kissing. Kissing led to feeling her tits. Feeling her tits led to undressing her. Undressing her led to finger-fucking her. By then, she was completely naked under her wide-open topcoat.

At that point, Lenny thought of his conversation with Jack. “I’m going to stick it in this time.”

He took it out. She made no protest. Naively, he asked her, “Can I put it in?”

She nodded “Yes.”

He guided it towards her love hole. Just as it touched the fine hairs of her bush, it ejaculated sperm onto her triangle. He was disappointed.

She said, “It’s okay.”

Despite the fact that he continued to meet her when he patronized her bank, Lenny was so embarrassed by his premature ejaculation that he never asked her for a date again.

Weeks passed. One Thursday evenings when their class met, Lenny avoided Jack, or Jack avoided Lenny. I don’t know which. They just didn’t have compatible interests.

But, Lenny finally succeeded in accompanying the “mature, well-built redhead” while exiting the class. It took four weeks of walking her to her car before shy Lenny worked up the courage to ask Barbara to dinner and a movie. Eventually, he did. She accepted.

The next day, a Friday, they attended a movie.

After attending the movie, Lenny drove Barbara straight home. He parked the car in the guest parking area of her condo, shut off the ignition, and tried to get a kiss from Barbara.

“Too many people coming and going around her to try to smooch. Let’s go upstairs,” she responded.

As they walked upstairs to her studio condo, they exchanged pleasantries. She offered him a cup of coffee “to help you stay awake on your way home.” He accepted her offer.

Her comfortable studio apartment consisted of one large room that served as a kitchen, living room, and bedroom. A reasonably spacious bathroom kaçak bahis adjoined the living quarters. Barbara seated Lenny at the kitchen table, and excused herself to the bathroom. When she returned, she was in a white bathrobe with a cloth tie around the waist.

When Barbara bent over to serve coffee to Lenny, his eyes easily detected that she was naked under her robe.

“I saw you peeking,” she said with a smile.

His face turned red as he stammered out an “I’m sorry.”

“Don’t be. I’ve been wanting to catch your eye for weeks. Would you like to sit on the couch near me and talk for a while longer?”

“That would be nice,” he said cautiously.

Barbara took him by the hand, led him to the couch, gave him a quick kiss on the cheek, and seated him. Before she could step away, Lenny took her hand and sat her on the couch beside him.

They kissed. She calmly placed her hand on his growing bulge.

“Don’t be shy,” she said.

His hand reached for her breast and fondled it through her robe. She kissed him harder. His hand reached through the plunging neckline of her robe and found her bare breast. He thrilled at the feel of her firm nipple. His penis swelled within the confines of his trousers.

“I’m not afraid of this bulge in your trousers,” she said. “You can take it out if you want.”

Lenny thought, “This girl is hot-to-trot. I’m going to fuck her – if she lets me.”

Barbara acted. She took Lenny’s penis out of its hiding place and started to massage it. He didn’t resist.

Barbara slid from the couch onto her knees. She put Lenny’s dick in her mouth. Her head went back and forth. Her lips applied gentle pressure to his shaft. His hips moved in harmony with her head. He uttered a loud gasp as his semen leaped into Barbara’s mouth.

As Barbara stood up, she let her robe slip to the floor. Completely naked except for the elastic band holding her ponytail, she asked Lenny, “Will you stay here with me tonight?”

Lenny thought, “Wow, what an offer. I’m alone in my condo. No one is waiting for me.” He said aloud, “I have no pajamas.”

“You won’t need them.”

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