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Former Cheerleader Needs $200

Category: Mature
24.03.2018
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I am a product of thinking patterns and values that were probably always wrong and early training to cherish women. Love and respect was without question the basis of male and female relationships. Until just a year ago, I struggled to find dates my own age or denied my age in an attempt to attract healthier, younger, more active females. Stupidly, I competed with the young broad shouldered, narrow waisted, handsome, deep voiced twenty and thirty year olds. If that is what the women wanted, I could not compete.

I have poise, education, success, financial stability, humor, health, vitality and know how to please my lady. However, I am a young looking, retired, sixty-six.

I knew women always make the choice to have sex, but when I read “Why People have Sex” in 2007, foreign ideas began to gel for me. I was presenting myself all wrong. There were women out there, of all ages, who would find what I had to offer attractive. The mystique died completely in 2009 with the follow-up work “Why Women have Sex.” By then, I could have written the book myself. I had learned to attract the women looking for strength, financial stability, respect, a gift, a cruise or security. Don’t make the leap that I’m finding prostitutes. I don’t have youth but I do have money. Read the book. Cindy Maston and David Buss found 237 reasons that women have sex – for revenge, saying thank you, stealing a man away from another female, getting the male to do things, keeping her relationship together, paying bills, duty and even to relieve pain. Sure the love, feel good and lust elements were high on the list but their works showed women traded or engaged in sex for dozens and dozens of reasons that were rare or non-existent in the male mind.

To test my newly defined playing field, in 2007, I asked a woman almost my age to go on a cruise with me and indicated that I would expect some intimacy. She said, “No,” but her younger sister, called me. We have been on two very enjoyable cruises now. Even most of the professional “sex workers” I meet in the local strip club where I shoot pool, seem to appreciate the lack of drunken gamesmanship. Up front now, wherever I am, I accept that what I have to bargain with is different than what the testosterone driven, young and handsome studs, so proudly display.

Let me give you a short, actual example. It happed at the strip club. Please don’t judge, just consider.

——————

“Megan told me to talk to you.”

“She is a lovely dancer. I have known her for years, she has danced for me dozens of times and I always enjoy her wet luscious body. But why would she tell such a beautiful young woman who does not dance here, to come talk to such an old man?”

Her hands trembled and she could not keep her nervous eyes looking at me. She tried to speak twice but aborted her words both times.

“Is Megan a friend of yours?”

“She is a friend of my older sister. We’ve known each other for ten years.”

“I bet you were a cheerleader or homecoming queen.”

“Cheerleader. How did you know?”

“You are tiny, athletic, very pretty, your complexion is clear and your body just demands attention. What shall I call you tonight?”

She blushed at my sincere compliments and said, “Sherri.”

Megan was nude twirling around the pole. My tiny companion looked away, embarrassed to see her nude. I took Sherri’s hand, pulled her to the rack, sat her down and motioned to Megan. I put a ten in front of my new, uninitiated partner. Megan rubbed her breasts into her friend’s face and almost touched her shaved cunt into Sherri’s shocked, gaping mouth and jutting chin.

When the song ended, we walked back to our secluded, dark bar height table and stools. “Did you smell her wetness? I really enjoy the smell of Megan’s pussy.”

She did not answer. When she diverted her eyes again, I asked, “Sherri, if you do not answer my questions how will we learn about each other and talk? Did you like the scent of Megan’s pussy?”

“Yes.”

“You should tell her. She likes most women more than she likes most men.”

Still she did not talk to me. I motioned to Megan as she finished her set.

“I cannot get this beauty to talk to me. It took me three tries to get her to admit that your pussy smell’s good.”

She had to rush to a table dance but she took the time to scold me, “Damn, Carl, you are scaring this poor woman to death. She needs some help and I told her you are about the only one who she should trust and talk to. She needs two hundred dollars tonight or she will be evicted in the morning. She has a kid and was with an asshole, who just left her high and dry.”

“Sherri is all that true?”

“Yes, I feel really stupid. I wasn’t working when Matt left. I’m busted and the bills are coming due.”

“Why did Megan send you to me?”

“She said you are playful and gentle. She also told me, that you don’t get drunk or abusive. That you are generous and don’t demand sex.”

“What did she tell you that you might have to do for me?”

“I might have to kiss you, talk to you, tease and let you touch me.”

“I’m much older than you. What are you 22?”

“23.”

“Are you okay with what Megan told you?”

“I’m frightened, but yes, I’m okay with it.”

“What would you like to drink while you tell me all about your likes and dislikes?”

“A Long Island Ice Tea, if that is alright and not too expensive.”

“You look hungry, when did you eat last?”

She did not answer.

“Conversations are tough with you.”

“Yesterday at lunch, I had free stuff at Costco.”

“How about your little one?”

“He’s alright. I’ve had enough to feed him.”

“Order some food with your drink. Let’s at least get you fed.”

“I need more than that. What do I have to do?”

“First you have to relax and enjoy your time with me. Smile, eat and have fun with me. I’m not going to kill you, hurt you or rape you. You might even enjoy my company a little bit.”

For this tiny thing, the Long Island was strong and she ate the biggest burger with no onions on the menu. We talked only about her while she ate. She was loosening up and starting to laugh with me and joke with the few people who stopped by.

“Are you driving tonight?”

“No, I don’t have a car. Matt took it when he left. I’m riding with Megan so I’m here until twelve.”

“Well, it’s a little after nine. I have to leave at eleven. Have another drink and play with me.”

She was going to object but I put two hundred dollar bills, folded so they could not be seen, under the napkin dispenser on the tall table. I scooted closer to her with my back to the bar. When her second drink was delivered, I held it away from her.

“Kiss me for your drink, pretty lady.”

I got a tiny peck. I motioned Megan over. “Wait for the boss to go into the back and show this shy thing how to kiss for a drink.” Megan showed off nicely and licked my tonsils so my cock started to rise. She reached down to check and took my table partner’s hand to prove the effect of her kiss. Sherri was small and her hands were proportional with short fingers. She started to pull away but was curious, so she pressed her hand into me for a few moments. Her fingers could not close around my cock.

“Sherri, Megan is a kick, but that is not what I had in mind.” I held her hands. “Look at our hands. Relax, my fingers are clean and my nails are smooth. Please hold my hands and come stand between my legs and let me kiss you.”

Our first kiss was sweet; she let my hand pull away, trail lightly up her body, caress her neck, her ear and hold her. I used my other hand to press gently at her chin, open her mouth and slip my tongue into her when she relaxed. She inhaled sharply; I was ready and breathed into her lungs when she did. Her eyes were wide open and glistening.

“Now you exhale.”

She did and thoroughly enjoyed the new feeling of me sucking her breath from her lungs into my chest. My little moan of enjoyment pleased her. I teased between her lips and gums with my tongue. She was stingy, so I told her, “Suck.”

My tongue waited patiently for her first trial efforts. I let it grow in her mouth and my wetness flow with it. She lost some of her embarrassment and it hardened for her. She had caught on to the fantasy tease. Her eyes closed and she sucked it like a small cock. When she let it go, I praised her, “That was beautiful Sherri. You played with me. We could learn to be very good at kissing. Your mouth is soft, wet and yielding. I enjoyed tasting your wetness.”

She was ready for another kiss but I pulled her stool closer, she sat and we talked, looked into each other’s eyes and drank. I figured she needed three for me to look reasonable to her.

“Which of your breasts is the largest?”

“The left one.”

“Which nipple is the most sensitive?”

“The left one.”

She was not quite tall enough for her breasts to be above the table; but gently, I began to rub her left breast and then roll her nipple too lightly between my thumb and forefinger. We talked as I caressed her. After a few minutes, I pulled away and she pushed to follow my hand.

“May I kiss you again?”

“Yes.”

This time, with her on the stool, I stepped between her legs, she tilted her head up and we kissed; more experienced this time. She did not seem surprised when my left hand crept over the top of her buttoned blouse and my fingers teased their way into her bra and moved all around her standing nipple and gently teased over it, as my fingers retreated. Her second drink was almost empty. I would be handsome and young after the next. Her eyes stayed closed and I reached under her skirt and timed my touch high on her thigh with my lips on hers. She had on thin panties, with a strap that went back between her cheeks. The crotch was wet and she did not resist my tickling fingers along her slit and around the protruding nub at the top.

“One more kiss my lovely and I’ll get us our last drink before I have to leave.” Her tongue welcomed me and her hips rolled to give me access to the edge of her panties. At first, I sucked her tongue in time with my middle finger gaining entrance into her wetness. When I was palm deep, I gave her my tongue and she sucked in time with my slow even thrusts.

Her eyes were wild and her expression complained when I withdrew my finger because our drinks were being served.

“Trust me?”

“Yes.”

“Close your eyes and open your mouth slightly. I am going to kiss you.”

She was ready for all except my finger. It was wet with her juices and I slipped it between our lips. She caught on quickly and sucked and licked for them with me.

Her body wanted release; we were seated in the darkest corner of the bar, near the seldom used ladies room. “Go remove your panties and come back to me so we can enjoy our last drink.”

She started to object. “I will not hurt you, embarrass you, only please you and then you can pay your rent tomorrow.”

She came back to me in two minutes and sat with her legs slightly spread, close and asked, “Will you kiss me again?” Just before our lips met she added, “Sometimes I make little noises. Tell me what to do.”

“Do not worry little one. I will protect you and tell you what to do. You just do what I tell you.”

We drank half our drink and I said, “Come to me.” She leaned forward and kept her ear next to my lips. I hinted what was going to happen, “Hold on to my shoulders while we kiss. If it gets too intense, slip you mouth to my neck and bite the collar of my shirt.”

Her eyes said she almost understood. She leaned forward and we kissed like experienced lovers. My body blocked my fingers as I had her suck and lick them making them very, very wet. Her thighs flared and her hips tilted when my two fingers slipped down between her legs. Just the finger tips touched when I spoke to her, “Sherri, I am very oral. You cannot imagine how I wish my fingers were my lips and tongue slipping into you.”

She moved first to take the tips of my fingers. I centered them with my slippery thumb on her clit and pushed smoothly all the way into her wet, yielding, sucking sheath. My thumb played for a while but I could tell she needed to feel my fingers push into her g-spot and stretch her. Her hips moved more than my hand did. The nasty stripper was blasting us with “I’m going to fuck you blind bitch.” The dirty words seemed to inflame my little plaything. I was attentive and worked to keep my thrust in time with her humping hips. She whimpered into my mouth. I felt her wet lips trail down my cheek and onto my neck. At first her teeth caught some of my skin but they pulled away, clinched on my collar and her body trembled. The song was just beginning. I had heard this long version a dozens of times. I matched my movements with the length of the song, forcing her to slow and hearing her body complain.

It was Megan dancing again. She had watched us and guessed correctly; she increased the volume to mask Sherri’s sounds; she dropped the lights to only the spot on just her and called out to the audience for attention so no one would pay attention to the dark corner. Sherri began her climb, oblivious to the world. Her stool rattled against the floor. I felt her drool through my collar onto my neck and I felt her cunt begin to suck harder at my fingers. In just moments, her scream was muffled into my collar but my fingers did not stop when her hand grasped mine.

“Take it Sherri. Suffer another climax for me. Let me watch your beauty. Fly for me.”

The loud song was about over, when Sherri screamed again and grasped my hand with both of hers. At first, I thought she would win and push me away but her body convulsed and went limp just notes before the end of the music. I held Sherri so she would not fall off the stool. I licked away some of her wetness from my fingers and wiped more on her upper lip and cheek. Only Megan knew. She came to me after she dressed on stage.

“Megan, our visitor has had too much to drink tonight. Get her a place in the dressing room to rest. I will carry her back.”

More than the two hundred made it into her purse. She was so tiny and light in my arms. I could not quit thinking about how beautiful her body would be slipping down my cock, seeing it throb in her at her belly button, hearing her scream freely and watching her excitement before she collapsed with me pouring into her.

“Megan, she will be happy with what is in her purse. Please get her home safely. She could please me day and night, but I am not what she wants. Thank you for letting me help.”

“I’ll take care of her, Carl. You take care of me next week.”

“Any way you want, Beautiful. Here or you know where I live. You know, you take my breath away and that I am wild about how you taste. You always have too many suitors to pay attention to me.”

“Not true, old man, and you know it. You have reduced me to putty several times like you did Sherri tonight.”

“Maybe but I have to call 911 for two things every time you leave my house. First to get my heart started and second to get my cock to go down.”

“You say the sweetest things. Take a nap in the afternoon and make sure it is in working order next Sunday night. I’m going to need $500, to please you and to cum at least four times before I pass out.”

“Will we argue again, like last time, about who cooks breakfast while the other has to service the cook?”

“No, you cook this time. We’ll see, if you do any better. Remember, I cooked the eggs too long and burnt the toast.”

“Okay, but I really enjoyed you using my cock to stir your orange juice last time.”

“In my glass or in my mouth?”

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