O’Grady’s was a young people’s bar on the near north side of Chicago. You could enter from the alley or the street; the bar itself ran almost the entire length of the room ending in a long ‘J.’ I sat at the end of the ‘J’ where I had equal opportunity to observe who entered from either entrance. I sipped my beer that early Friday evening; the crowd would start in about an hour. Shortly afterward it would be elbow to elbow; smoke and noise. Females would be slightly outnumbered, but not by much. That statistic was the reason for my early arrival ... maybe tonight would be the night?
Larry Jackson is my name. I am a recent graduate of a Midwest college where I majored in computer science. My first interview was my last; I joined a major software company located in Chicago and was in my second month of a lengthy training program. At six feet tall with brown hair and brown eyes and no fat on my 190 pounds, I thought I was good, but not great looking. However, if some girl tonight decided on great, I wouldn’t argue too hard.
For two months, several times a week I sat at O’Grady’s. I never missed Wednesday or Friday night, since those two nights seemed to attract the greatest number of females. Despite my due diligence, my score card was pretty empty. I grew up on a farm far from the nearest town so I never received the proper socialization required to attract and keep the opposite sex entranced. I long ago concluded that my efforts to enjoy the pleasures of sex rated at least a B, but my execution was an F—and that score might be generous. So I took up my position at O’Grady’s, hoping for the best and expecting the usual.
The bar had by now started to fill. There were two empty seats left at the bar and the waiters were starting to attract beer orders from clumps of people commingling on the floor. I heard a female voice next to me yell at the bartender, “Damn it Frank; if you would look around you might find 500 or so customers that need a drink ... especially me! Will you get off your ass and bring me my usual?”
Frank grinned at her from down the bar, gave her half a finger in a joking way, and shuffled over to mix her drink. While she waited for speedy Frank, I checked her out. She was a nice looking blond about five feet six inches or so, big breasts hidden by a colorful sweater, and very nicely tapered legs showing beneath her skirt.
“Can I buy you that drink?” I heard myself say. She turned to check out the offer. She had blue eyes and high cheek bones; definitely a class face. I saw instantly, however, that I missed one key item; she was old, at least twenty-five or so to my twenty-one.
I knew that she also spotted the age difference; the four years were like 20 for those into the bar scenes. I could see her thoughts turning to voice as she was about to put me in my place. For some reason she stopped whatever she was about to say, gave my hand a little squeeze and with an ironic grin said, “Thanks, but I’m a little too old for you, and I’m usually a pain in the ass, but thanks for the offer.”
It was a gentle put down, but the arrow went deep. She saw my hurt, but Frank came up with her drink and she was gone.
I couldn’t help it—I sipped and sulked for another hour or so. O’Grady’s was now packed. Chairs at the bar were sold for ten dollars so that someone could sit next to their date. The floor was packed; the waiters fought through the crowd to deliver beers and accept tips. I thought to myself, “Another 45 minutes or so of sipping and I will call it a night.”
My elbow was tapped from behind me twice. I swiveled in my chair and found the nice looking, but tough blond in front of me. She grinned and said, “Your luck is as good as my luck; why don’t you offer to take me for a walk out of this smoke filled den of sin and booze.”
I dropped a couple of bucks on the bar for Frank and we were off through the alley exit. We came out on the street of bars—all of them like O’Grady’s but with different names. We walked without talking for a block and she turned onto a quiet street. Not a word had been spoken yet. Finally she said, “My name is Jenny Collins ... and you?”
I answered, “Larry ... Larry Jackson that is. I’m a computer nerd going through a year long training program. O’Grady’s gives me the chance to remind myself that the world isn’t just made of computers.”
Jenny replied, “Nothing is wrong with computers or the ones that make them go. There is money in those things.
“If you don’t mind walking a bit to get the smoke out of us, tell me about yourself Larry.”
And so I told her about growing up on the farm, the high school and college highlights and how impressed I was with myself to finally be living in a big city like Chicago. She asked me questions and got me talking some more. We walked for an hour and Jenny asked the questions and I did the talking—I couldn’t stop talking to this female, who was beautiful, who was paying so much attention to me.
Finally Jenny stopped walking. We were in front of an apartment on one of those Chicago tree streets—Oak, Elm, Chestnut or one of those. She looked at me and said, “This is where I live. Do you want to come up for a while?”
I was shocked. Jenny was way beyond my league, and yet she was asking me to go into her apartment late on a Friday night. I was elated; I was scared. I was hoping that I could fake my lack of experience.
“Sure,” I said. “I’d like that.”
She took my hand and led me up the stairs to the second floor. She unlocked the door and pulled me in. Her hand flipped a switch and a table lamp came on somewhere in the room. I looked into her eyes; afraid to do something, and afraid to do nothing. She grinned and stepped closer to me. She said in a teasing voice, “Can’t a girl get a kiss without waiting forever Frankie?”
I moved into her and brought my lips to hers. I felt her tongue force itself between my lips and our tongues met, and teased each other. I pulled her closer and felt her breasts pushing against my chest. I kissed her harder. She took my arms and pulled them down. Taking my hands in hers, she raised them to her breasts and covered each of her breasts with my hands. I felt the softness of them; I squeezed them gently, not wanting to hurt but wanting to feel. She took my hands again and brought them to the bottom of her sweater. They slipped under her sweater and I felt her bare midriff. My hands explored her stomach moving up to her breasts and our kiss continued. As I reached her breasts she said, “Take off my sweater; it will be easier for us.”
She lifted her arms as I pulled the sweater over her head. She stood there in her bra. Her breasts strained against the material. She whispered, “Now my bra.”
My hands went around her searching for the clasps. I found them, but they wouldn’t open. I was embarrassed that I could not get Jenny’s bra off, but my fumbling so close to her breasts was causing me to have an enormous erection. Finally, one of the combinations worked, and her bra fell from her arms. I stepped back and saw her breasts. They were large with a little sag, the nipples were small. I touched one of the nipples and it began to harden.
Jenny suddenly grabbed my hand and dragged me into her bedroom. We stood face to face. Looking at me she kissed my lips and stepped back. She kicked off her shoes and removed her hose. Then her skirt fell. She slipped her fingers around the elastic of her panties and pushed them down. She stepped out of them and faced me. My eyes went to her pussy. It had been trimmed for a small swimming suit bottom. I looked up and she stepped up to me; she undressed me.
By the time she pulled my shorts down to my ankles, my erection was unbearable. She pulled me as she lay on her back on the bed. My lips went to hers and we kissed, I assaulted her nipples with my tongue. My penis was moving over her vulva searching for an opening. It found her vagina and entered her. I came almost immediately.
The release was fantastic. My thoughts were horrible. My first time and I did everything wrong. Did Jenny come? Was she even aroused? I was embarrassed.
Jenny drew my body up to her and gently kissed me on the lips. Jenny said in a quiet voice, “I did a very unfair thing to you and I want to talk about it now. I knew that you had little sexual experience; it’s not hard to spot. Maybe this was even your first time?”
She looked at me and I nodded my head.
“I think you’re a nice person who is just starting his adult life. Some things come easy and some don’t. Having sex is easier than programming computers, but experience is the teacher—not some books or porn pictures or whatever. I have a proposition for you. I will teach you what it takes to make a woman enjoy sex. What do you think?”
I stopped the urge for instant agreement, and asked, “What is my part of the deal?”
Jenny sighed and said, “There is no short answer. Snuggle up to me—touch me if you want—and I will tell you about your part of the deal, but it will take a while.
“I grew up in a small town in Nebraska. It was my younger sister, my mom and dad. Things got financially difficult and dad started drinking. He was becoming older and meaner, but before anything really bad happened, he left us. I have never heard or saw him again since I was a junior in high school. In my senior year, my mom got cancer. Six months later she died.
“It was only Beth and me. Beth was just entering high school. My job, my obsession was to make Beth happy. College was out, but with a little insurance money, selling the house, and a minimum wage job, we managed. Beth made it through high school. She was a cheerleader and an athletic. She applied to a college near Boston and was accepted.
“Of course the problem was money. I was working hard, but with no college, big salaries just weren’t there. When I turned twenty-one I saw a chance. I married a person who had money. Maybe there was some love, but there was money to pay for Beth’s college. I wasn’t a virgin when I got married. You might describe me as a street smart female who did what she had to do. I’m not proud of things I have done, but I’m not embarrassed either. Life is a lottery, and most people don’t win.
“Well, when you marry for money you generally get what you deserve. Sixteen months of agony and then the divorce. He was nice about it. I received enough money for the rest of Beth’s tuition. Three year’s later I am about 10 credits shy of a college degree from night school, and my company has promised me a big promotion when that degree comes.
“So I guess you would call me an old 25 Larry.”
I had turned on my side facing her on the bed. I said, “You’re not old Jenny; you’re beautiful.”
She laughed and continued, “Eventually you would think of the question ... why are you here? It’s Beth again. She is everything to me; I would do anything for her, anything! I have sheltered her from a lot of the real world. My hard knocks have not been her hard knocks. She looks up to me. Beth wants to be me not knowing what I am.
“We talk every week. Two weeks ago we got into a long conversation. Beth was almost in tears. She is still a virgin. All her friends are sexually active and she is not. Beth is stubborn and she is convinced that to lose ones virginity is the beginning of adulthood. Nothing I said changed her mind; she can be as stubborn as me. I asked her to visit me on her Spring break and we would talk about it more. Her last words were, ‘We can talk, but her visit to Chicago could be the start of her adulthood.’
“Larry, if she is determined to go through with it, I don’t want it to be any pick up on the street. A quick fuck and that’s it. If she wants to fuck for the first time, I want it to be with a nice person who will be gentle with her and start her sex life upbeat and not with some guilty post depression trip. If you agree, I want it to be you.”
“Me?” I gasped. “Why would you ever want me to have sex with Beth when you just saw how terrible I am doing it? I don’t know anything.”
“But that’s the point Larry,” Jenny replied. “You know how it is to be inexperienced. You know how people can put you down—like I did to you at O’Grady’s. I need someone like you to cushion Beth and to help her. If she becomes afraid and wants to stop, I want someone who will stop. If she is determined to go through with it, I want it to be a wonderful experience.”
“How can I make it a wonderful experience?” I asked.
“Because I will teach you,” whispered Jenny, “To make Beth happy. Will you do it?”
There was no other possible answer. “Of course I will,” I replied.
“OK,” Jenny said, “First lesson; into the shower.”
I got up quickly and headed for the bathroom. “Wait,” she commanded. “You just got out of bed facing away from me and walked quickly to the bathroom door. Are you in a hurry for a shower, or are you afraid I will see your body? Come stand in front of me.
“Larry, we don’t have that much time. Your body is beautiful. Stand still.”
She took my half erect penis in her hand and said, “Don’t be so shy. If you are, you will make your partner shy. Size isn’t what it is cracked up to be, but if you want to know, your penis is above average in length and it is thicker than average also. Now watch when I cup your balls and squeeze. You just grew to about 90 percent. How does my touch feel?”
“Wonderful,” I croaked.
Jenny continued, “Now Larry take your hand and lightly explore my vulva. Cover it with your hand and rub a little. Take your finger and move it up and down my lips; push your finger in and touch me. How does it feel? How do you feel?”
I replied softly, “I’m aroused and I’m a little embarrassed. This is new and strange.”
Jenny commanded, “Give me a kiss; use your tongue.”
I came closer to her and we kissed. Our mouths opened and my tongue probed her tongue. My prick was pressing against her. She moved her hands from my back and one slid down to my ass. Suddenly her finger was pushing into me.
I broke the kiss. “What’s wrong?” she asked.
I said, “Your finger was going into ... into...”
Jenny interrupted, “The word Larry is asshole. My finger was exploring your asshole, and you were surprised and embarrassed. The lesson I want you to remember is you should do anything with your partner’s body that they enjoy. We aren’t going to mess with your asshole Larry, but some time you might have a partner that wants you to explore hers, so don’t be timid. Have fun.
“Into the shower.”
She soaped up two wash rags and washed me everywhere. She teased my body mercilessly. Then she commanded me to do the same to her. When I reached her vulva my hands explored her relentlessly with the soapy rags. After five minutes of wiping and probing, Jenny moaned in anguish.
She said, “Enough. Rinse us off and we will dry each other. Then back to the bed.”
Back on the bed she said, “Beth will be here on Thursday. I will be with her Thursday, Friday and Saturday morning and then I will be gone. Your date with her is Saturday night. My apartment is yours. We don’t have much time.
“Turn on a brighter light Larry, and push the pillow under my hips so that you can see me better. Now touch me. My lips are partly open; spread them with your fingers. Look for my clit and touch it. That’s it ... not too hard. Be gentle. Trace your fingers inside me; now push your finger into my vagina. Good. Now two fingers. Move them in and out just a little. Yes. Now I want you to kiss and lick—tease me until I tell you that I am ready. When you are kissing me you will be very erect; try not to rub yourself against me as it will make you come too soon. Then I want you to come into me again. The idea this time is for me to come.”
So I started kissing her. Her mouth was first. At some point I licked her breasts and then her nipples. I went to her inner thighs and licked and kissed. Then my fingers touched her labia and probed. Jenny was started to moan. She spread her legs wider. I parted her lips and my tongue explored her insides; broad strokes with my tongue; then penetrations with my tongue into her vagina. Finally I focused her clit. She gasped as I teased it; my tongue gradually applying more pressure and speed. Finally, she whimpered, “Hurry, put it in me. I knelt between her legs and guided myself deep into her. I could feel her vagina squeezing me, and as she came, I came. When it was over I lay next to her and gently kissed her lips. I whispered, “Thank you.” She squeezed my hand.
Later I dressed and as I was leaving, Jenny called to me, “Eight o’clock next Wednesday for your final coaching.”
When I arrived on Wednesday Jenny said, “Off with your clothes.” I stood naked in front of her; there was little embarrassment now after our last time together. I made her come by tonguing her clitoris with no penetration. We both came after 20 minutes of my mouth teasing her body. After a sensual shower, she took me by the hand and sat me at the edge of the bed. She knelt down and taking me in her hand said, “This is crudely known as a blow job. It can feel wonderful if done correctly.” It was wonderful; it was done correctly.
As I was saying good night to Jenny she said, “A few last things. Beth is expecting her blind date to come to the apartment at six o’clock for a dinner date. When you arrive, I will be gone for the night. Take her somewhere nice. What happens after that is up to Beth and you. If she invites you back to the apartment, be gentle; she is everything to me. I forgot to mention two things. If it goes that far, do not worry about the pain of the first penetration. Her soccer playing fixed that difficulty in high school. She also told me she is on the pill so that she would ‘be ready.’
I kidded her, “Jenny, you’re acting like a worried mother.”
She looked at me and I leaned forward for a kiss. She kissed me lightly on the forehead and said good night.
It was Saturday night and I was knocking on Jenny’s door waiting for my first glimpse of Beth. The door opened, and she said, “Hi, I’m Beth, and I sure hope you’re Larry?”
I laughed, “Good guess Beth. I am Larry and tonight my job is to be your tour guide through the streets of sin—better known as the near north side.”