The Cherry Popper

I'm 72. I'm widowed. I lost my wife two years ago. For work reasons, our children live in different states. I'm very much alone. At least I used to be.

We had a good sex life until about six months before she passed away. Older people do not die below the waist, contrary to what young people believe. Even when I was cut off by her illness, I practiced self-abuse. A couple times, she suggested I find a lover. Even with her permission, I could not bring myself to cheat on her. It could be argued that it wouldn't be cheating if she knew about it and/or condoned it. After 48 years of marriage, there was no way I could consider an affair.

The children and grandchildren came to the funeral, of course. Bereavement leaves are limited. The grands had to return to school. Within ten days, it was me and a big empty house. The holidays brought the youngsters home for a few days. All the conversations were about mom and grandma. When spring break rolled around, they announced another visit. I told them to stay home and get on with their lives. I loved them dearly, and they meant well, but the memories they insisted on discussing were getting too painful. I, too, had to begin a new life.

They may sound odd, but one of my biggest adjustments was grocery shopping. My wife had had a couple food allergies. I had liked the items she could not have, but I didn't bring them into the house out of respect for her allergies, and to avoid rubbing it into her face that I could have them when she couldn't. On one of my first shopping trips, I started to pass by one of her no-nos, then stopped. I could have that now, so I bought it. It was one of my early guilty pleasures.

Spousal estates are supposed to be simple to settle. That's a big myth. I had to notify Social Security of her passing. Her name had to be removed from the bank accounts. Her cell phone had to be shut off. Her health and dental insurance had to be cancelled. Almost every office wanted an original death certificate. I went through ten at thirty dollars each.

My visits to Rosy Palm and her five daughters provided some relief. Those visits gradually became less frequent. Baby oil and petroleum jelly provided lubrication, but they were no substitutes for a tight, wet pussy.

Eventually I tried meeting some new women. I checked out the singles' groups, but their members were not in my age range. My attendance at meetings was not rejected out right, but definitely not encouraged. Most of the women were divorced. The few people I talked with said they mostly talked about how terrible their exes were. After 48 years of wedded bliss, I didn't need that.

One afternoon when I was checking my email, I received a message from a dating website. Horny women would contact me, it said. Signing up would be free. All I had to do was post a profile, and I would be propositioned by single women, divorcees, and cheating wives. What did I have to lose? Certainly not my virginity. That ship had sailed decades ago.

I signed on to fill out a profile. The first part was easy: a screen name, my age, a physical description. Then came the hard part. What kind of relationship was I looking for? Did I want to something long-term possibly leading to marriage? I hadn't given any thought to remarrying, and I wasn't sure I wanted to. A single woman would probably want a man with that inclination. Perhaps a friend with benefits. An affair with a married woman. It might be fun to cuckold some guy behind his back, especially if his wife preferred me to him in bed. Her marriage would keep her from wanting to tie me down. What about a one-night stand? A prostitute would fill that niche. Why sign up at all? I finally entered that I was looking for someone between the ages of thirty and sixty-five and with no preference for type of relationship. What might work with one woman might not work with another. I attached a recent portrait because the site said it would generate more replies.

An hour later I had received twenty emails. All had photos attached. Three of the women were fully dressed in party attire showing strong legs. Two were completely naked and spreading their pussies with their fingers. A few showed their breasts, and the others were fully nude but tastefully posed. The list included wives looking for affairs, single women looking for husbands, and some who wished to date and see where things went. One was outside my desire age range. She was only eighteen. I started to erase her message but stopped to look at her picture again. She was completely naked. Her breasts were firm B-cups. Her pose was relaxed. What I noticed most was her smile. She made no attempt to be sexy. She simply was happy. Her name was Nancy.

I drafted a reply complimenting her on her looks and gently pointing out that not only was she outside my desired age range, but that I was also old enough to be her grandfather. When I clicked the send button, I learned why signing up was free. Sending messages was expensive. The introductory package was ten messages for twenty-five dollars. Other packages brought the per message cost down to a dollar, but it was priced at three hundred dollars for three hundred messages. I opted for the introductory package not expecting to continue my membership for very long.

Fifteen minutes after clicking on send, I received a reply. "Hi, Matt, I'm Nancy. Thank you for responding to my email. I realize I am much younger than your specified age range. I was very afraid you would consider me too young and not bother to reply. Your profile struck a chord with me that I really can't describe. Unlike other men who have emailed me, you were the politest. Younger men want to get me into bed on a first date. Even though you were trying to discourage me because of our age difference, you weren't condescending or mean.

"I'm not looking for a long-term relationship or a husband. I'm eighteen. After I graduate from high school, my family is taking a vacation to Europe before I go to college. I will major in music and minor in education. That way if I don't become rich and famous by singing, I can teach music.

"I don't have a boyfriend. Guys my age seem to only be interested in sex. What I really want is a friend I can talk to, who will listen to me without judging, who will hold me and make me feel safe, who will care for me without stifling me. If I read your profile correctly, I think I'm describing you. Please be my friend.

"Nancy."

Her words of desire for a romantic, yet platonic, relationship conflicted with the photo of her nude body. Was she as confused about what she wanted as I was? She acknowledged the gap in our ages but gave no sign as to whether it mattered to her. I was tempted to end the conversation, yet curiosity compelled me to write back: "You write well, and you are open your goals. Somehow, I wonder if you really understand what is at stake. You don't want a committed relationship, yet you speak of the desirable attributes of commitment. On top of that you sent me a picture of your lovely body that awakens lust in me. Perhaps you should pursue a male peer whose needs are in tune with your own.

"Matt."

"I guess it's time for me to fess up. That picture was meant to make you horny. I want you to lust after me. This will probably make me look like a silly teenage girl. It's call peer pressure. I'm still a virgin. Many of my friends are sexually active. They brag about having a man inside them, about sucking cocks, about having orgasms. I want to do those things. I want the same pleasure they are having.

"The ones that gave their cherries to their boyfriends complained about the guys' ineptitude. They only wanted to stick their dicks into pussies. They didn't care whether the girls were in pain. Others opted for older men who knew what they were doing. They were considerate of the girls and deflowered them gently. Sure, there was some pain; it's part of being a girl.

"Matt, I want you to be my first. You're sweet and caring and loving and kind and all the good things a man should be. I don't care how old you are. Think about the girls you pleasured when you were young. You can do it again. I want you to teach me how to fuck a man. I want to give you the same pleasure that you will give me. I'm on the pill so you can cum inside me. I want to feel your man juices. After you've torn my hymen, you won't have to see me again. Just fuck me! Please!

"Nancy."

Nancy was right. I had no idea what to do the first time I bedded down with a girl. Fortunately, she was experienced and guided me through my first fuck. In my teenage excitement, I came very quickly. Even a half century later, I still remember her patience with me. Girls deserved the same patient treatment. Yet the fifty-four-year age gap did bother me. Chronologically she was a woman, but in my eyes, she was still a child. She was as desperate to be an adult as I had been at her age. The nude photo of her firm breasts and shaved pussy did excite me. I would have to shave too. "There is a lot more to ending your virginity than having your hymen torn. There is a learning curve to sex like any other skill, and sex is a skill. A proper setting is important. Your feelings and your lover's must be considered. You will probably hold back initially because you expect it to be painful. Nature is unkind to human females in that respect. The pain will be brief, just a few minutes; however, it can't be avoided. I would probably find the physical act enjoyable, but there is also an emotional factor. I have a granddaughter your age. I love her dearly, but I could never consider going to bed with her.

"Matt."

"I understand where you are coming from. I wouldn't sleep with my grandfathers, but you and I are not related. We could have a sex date. Lots of my friends do that. We could make it a business transaction. I'll pay you fifty dollars to provide a service.

"Nancy."

"I don't think the fifty dollars would be appropriate.

"Matt."

"Okay, I'll make it a hundred.

"Nancy."

I took a deep breath. She was not going to be denied. I supposed deflowering a virgin could be considered a service. Maybe I should start a business. There would be the matter of marketing. I couldn't run ads in the newspapers. "Okay. For legal reasons, I must see a photo ID confirming you are at least eighteen. I don't want your parents to charge me with statutory rape. Let's decide on where and when. I live alone so my house would work. Being retired, I'm basically available twenty-four/seven.

"Matt."

The website would not allow us to exchange addresses or telephone numbers through it. We were able to set up a breakfast date at a nearby restaurant the following Saturday.

I was still wondering if I was doing the right thing when I arrived at nine a. m. The fifty-four-year age difference between us could never go away. I had made an agreement, and I find a way to convince myself to carry out my part of the bargain. When Nancy parked her car beside mine a minute later and got out of it, I became partially ready to proceed.

She was even prettier than in her profile. She wore knee-high, high heeled boots and a skirt that came down to mid-thigh. Her coat was appropriate for February. Once we were seated, we removed our coats. Her shirt was tucked tightly into her skirt. Although the fabric was opaque, her nipples were clearly outlined through it. After the server took our drink orders, she took her passport from her purse and handed it to me. She was indeed eighteen. A one-hundred-dollar bill was tucked inside it. I tucked the money into my shirt pocket and returned the document to her. Now there was no turning back. I had accepted her money. I was officially a gigolo.

After we ordered our meals, she leaned across the table toward me. Her shirt was unbuttoned enough for me to see the tops of her boobs. "Is it okay for me to be scared?" she asked quietly.

"Anything new is intimidating," I said. "Your feelings are natural. If it helps, I'm nervous too. I haven't had a new partner in fifty years. I'm praying I can please you."

"Considering how kind you have been so far, I'm sure this will be a positive experience for both of us. I watched some porn movies on my computer, so I think I know what we will be doing. I did notice that many women kept their shoes on. Should I do that?"

"It doesn't matter to me. Wear as much or as little that makes you comfortable. You might be interested in knowing my wife played the piano. I still have hers."

"I should play for you. They make me play classical music in school. I like it okay, but I prefer the newer pieces. You probably wouldn't care for them."

"My wife was partial to Bach. I prefer Beethoven. When she was mad, I was treated to the 1812 Overture, but without the cannon. There were times she wished she had one."

"I like you. It appears we have more in common than we suspected."

Nancy followed me in her car to my house. As I closed the door, she asked, "What should we do first?"

"Let's hang our coats up," I said as I opened the closet door.

"Of course," she said with a sheepish expression as she handed me her coat. She noticed the grand piano when we entered the living room. "May I?' she asked.

"Be my guest," I said.

She sat on the bench and opened the keyboard. She played a quick scale. "It's even in tune. I want to play something for you."

"The sheet music is in the bench."

"That's okay. I know a few by heart." I recognized the piece at once. As I had done that last time I heard it, I sat beside her on the bench and put my arm around her waist just I had done every time my wife played Beethoven's Moonlight Sonata. Tears welled up as I recalled the many times she had played it for me. After about ten bars, Nancy heard me trying to stifle my emotions and stopped playing. "Am I playing the wrong number?"

"It's the perfect one. I love the Moonlight. My wife played it for me all the time."

"Matt, I'm so sorry. I didn't know."

"You couldn't have known any more than I could have known it would be your choice. Please play it."

She began again at the first measure. I closed my eyes and listened to the music. Gradually my tears ceased. The music calmed me, and I found the peace I so desperately needed. As she ended playing, Nancy turned to face me and saw my smile. She put her arms around my neck and kissed me softly. My free hand caressed her inner thigh beginning at her knee and slowly traveled up her leg under her skirt expecting to encounter panties, a thong, a G-string. No, there was a bare bald pussy. "You like?" she asked.

"Very much," I said.

"I'm ready to go to the bedroom."

We stretched out atop the bed covers facing each other. I brushed her cheek with the back of my fingers and gave her a brief kiss. She smiled, and we kissed again. "You are trying to get me to relax," she said. "I appreciate that, but I'm still nervous. Maybe a little scared, but definitely nervous."

"It's called anticipation," I said. "You know what's coming, but you still wonder if are ready for it."

"How do you know so much about being a girl?"

"It's natural for everyone." I kissed her again.

She placed her hand on my cheek and gazed into my eyes. This time she kissed me. My hand slid down her side. She giggled as I passed her waist. "I'm ticklish there." My palm rested on her rump. I gave her a slight squeeze. "That feels nice." My hand continued to the hemline of her skirt, then went underneath it and up her leg. She maintained eye contact with me as I caressed her warm flesh. Again she kissed me. "That feels even better. Is it okay if I do that to you?"

"I would love it."

"Your pants are in the way." I stood up long enough to completely undress, then returned to her side. "That's much better." She rubbed my bottom and gave it a squeeze. "I've never seen a naked man before. I've seen pictures, but they don't compare to the real thing. I should be naked too." She took off her shirt and skirt and struck a couple poses. "You did say I could keep my boots on?"

"If you so desire, yes. You look sexy with them on."

She returned to the bed and pressed her chest against mine. My cock began to stir. "My nipples have never gotten hard before." She ran her hand across my chest. "Yours are getting hard too."

"That means we are becoming aroused." I rolled her onto her back.

Slowly, softly, I kissed her cheeks, then her neck. Her eyes closed, and her breathing slowed. My fingertips drew circles around her nipples. Her breath became deeper. "That feels wonderful. You play my body like a violin."

"This is only the first movement." She gasped as I took a nipple between my lips and squeezed it. The other nipple soon received the same treatment. Her proud young breasts jutted upward as I smothered them with kisses. I attempted to kiss her ribs, but her ticklishness prevented me from doing so.

She looked down and saw my rigid cock sticking straight out. "The women in the movies put the men's penises in their mouths. May I do that with yours?"

"Be my guest." She kissed the tip a few times before placing the crown just inside her mouth. Her tongue touched my pee hole making me take a deep breath. She took another inch in, then another. Her head bobbed up and down as she strived to take my entire cock into her mouth. "Suck harder." Her lips formed a seal around my shaft, and her lungs pulled on my dick. When I felt the urge to cum build in me, I had her lay on her back.

Starting at her knees, I kissed my way up her inner thighs toward her pussy. Her breathing slowed and deepened as I approached her slit with my mouth. It had opened a bit allowing my tongue to trace its folds from the lower end up to her clit. She gasped as my tongue touched it. A drop of moisture sparkled at the lower end as I licked her slit again. Her hands held my head as I continued to dine on her pussy lips and clit. Her panting became deep and rapid until her thighs clamped against my head. Her hips shook. When her body relaxed, she asked, "What happened?"

"You had an orgasm," I said.

"I've never had one before. That's amazing. It was so incredibly intense. I loved it. May I have another one?"

"You are going to have hundreds in your lifetime."

"I meant now."

"That can be arranged. I am going to use a different technique this time." I crawled up atop her and rubbed my cock against her clit.

"Will doing that give me an orgasm?"

"This is the beginning." I placed the tip of my cock just inside her pussy against her hymen. She tensed up as I touched the membrane.

"It's that time, isn't it?" I nodded my head. "It's going to hurt. I knew it would, but I'm still scared."

"I know this sounds silly, but it will hurt less if you can relax."

"I can't." Her arms crossed over her chest in a protective pose. My fingertips lightly caressed her waist. She started to giggle. "Stop that." I tickled her some more. "You know I'm ticklish." Her giggles turned into laughter. "Please stop!" I felt her tension disappear and pushed my cock into her. "That hurts. It hurts! It hurts! It hurts! I don't like it. I want to stay a virgin. Take it out."

"Too late." I laid still with my dick inside her. "The pain will go away."

"Please take it out. It hurts too much."

Slowly I withdrew from her vagina. I raised my hips. "Take a look."

She glanced down at my cock. "You have blood on your penis."

"It's your blood."

"How did it get there?"

"It's from your hymen. You are no longer a virgin."

Her eyes opened wide in astonishment. "Really?"

"Really. How is the pain now?"

"It's going away."

"I'm going to put it back in you. Tell me how it feels." I slowly slid into her.

"It didn't hurt. It feels strange. I guess it's because it's new." I moved my shaft in and out of her. "Oooh, that feels good." She pushed her pussy toward me as I pushed inward. We found a rhythm to our thrusts. Gradually our pace increased. She wrapped her legs around my waist. Her leather boots excited me even more as I thrust harder into her. Her screams told me she was approaching another climax. Her arms around my chest crushed her breasts against mine. "Yes! Yes!" Her vaginal muscles gripped my cock as I emptied my balls into her womb.

Nancy stared into my eyes as she caught her breath. "That was so wonderful," she said. "I never thought sex could be that great. Now I don't mind that you made me pay for it."

"Wait a minute," I said. "The money was your idea. I never mentioned it."

"Then why did you take it?"

"I know when to keep my mouth shut."

"Can you fuck me for free in the future?"

"No, but I will make love to you. We must do it some more. You have a lot to learn before I turn you loose on the boys out there. There are several positions to learn. There is a proper way to do blowjobs."

"I want you to teach me. Several of my friends want to learn too. After we chatted online Tuesday, I realized I shouldn't be selfish." She reached into her boot and pulled out a card. "I made this on my computer." She handed me the card.

"'The Cherry Popper'," I read and laughed. A second line read, "Bring me your hymen." My laughter tripled.

"They would pay your fee," she said. "I would expect a referral commission."

"I don't believe you," I said. "You are one crazy woman."

Her eyes widened in astonishment. "Do you really mean that?"

"Ten minutes ago, you were a virgin. Now you want to be my madam. How is that sane?"

"I meant the other word you used. You called me a woman. It means so much to be considered an adult. Your phone number would have to be added. What do you think? Would you like to do it? Think about all the fun you would have."

"Hell! Why not? The standard commission rate for labor is fifteen per cent. I must insist on seeing picture IDs. I won't budge on that."

"That's good. I couldn't make any money off you if you went to jail."

"Let's clean up. After I've rested, we can try some other positions."

Monday afternoon my cell phone rang. "Hello?"

"Are you the cherry popper?" a female voice asked.

I smiled. "Yes. How can I help you?"

"Can you see me now? I've already paid Nancy."