Special thanks to Jim7 for his expertise in editing and proofing.
Being fifteen and nearly broke was not the best thing in the world as the summer holidays were ending. All my buddies were in the same boat. We were always daydreaming about what we would do with a pocket full of money. The summer was nearly over and my total earnings to date amounted to $35.20. With the cost of my wants, that wouldn’t last very long. I had canvassed the neighborhood for any small jobs such as cutting grass or painting with little luck. All the boys were looking for the jobs. We all managed find a little work but not enough to carry us through the school year.
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My parents helped but their funds were limited as well. My two sisters were currently available for babysitting which they did as often as possible. They’re a little ahead of me in the income department. But things were about to change. My mom called me.
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“Don. Here is an opportunity to earn some cash. The family that just moved into the Johnson house called looking for a babysitter. Your sisters can’t do it so I suggested you.”
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At this point I couldn’t be picky. I needed the money. It was to begin today at six o’clock. I was aware a new family had moved into the neighbourhood but didn’t know anything about them. The prior owners the Johnsons had moved because of a job transfer. The house had been for sale, and then a sold sticker showed up attached to the For Sale sign. Two weeks ago a large moving transport unloaded the new owner’s furniture.
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I was at the door just before six. A very attractive woman answered the door. She had black shoulder length hair. Her dark eyes were shining. But it was her large breasts got my attention. Then realizing she noticed where my eyes had settled, I stammered.
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“Hello. I’m Don Parsons. My mom sent me over for the babysitting job.”
“Hi, Don. I’m Avery Raven. Come in.”
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Following her very beautiful well-shaped rear that had wonderful movement, she led me to the living room. My guess was Mrs. Raven was in her early thirties. Her long well shaped legs were encased in form fitting black slacks. Avery’s perfume reverberated through my scenes. The scent seemed to go right to my core, something that had never happened before. My mom wore scent but nothing that made John Thomas respond as Avery’s.
“Alishia is in bed. She should be set for the night. I just fed her.”
Mrs. Raven led me to a child’s bedroom. Her baby was sleeping in a crib. It had me wondering if she breast-fed. Mrs. Raven certainly had the equipment for it. Staring at her I felt embarrassed. If Mrs. Raven noticed, she never let on.
“I should be home by twelve. Here’s a telephone number. If you have any problems call me immediately.”
“What time will Mr. Raven be home?”
Avery Raven smiled and said.
“There’s no Mr. Raven. I’m divorced.”
“Oh. I’m sorry I didn’t mean to pry Mrs. Raven.”
“Don. There’s no need to be sorry. There was no way you could’ve known. Please call me Avery. Mrs. Raven reminds me of the useless teat I married.”
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That comment made me a bit uncomfortable, Avery’s a beautiful woman, the type I thought about many a time while masturbating. I couldn’t wait for her to leave so I could relieve the building tension. If I were older; perhaps Avery would look at me as more than just a kid. My active imagination was working overtime. My total experience with women was nil.
Avery showed me the emergency exit and the fire alarm. I never knew there was a site plan for a building. I would ask mom if we had one.
“Do you have any questions Don?”
“Yes. When is the baby to be fed again?”
“I will feed her when I get home. That is something you aren’t equipped to do.”
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Question answered, Avery breast-fed her daughter. The baby must drink a lot of milk to keep her mother’s breasts drained. I wondered what it would be like to see breasts that had milk in them; my imagination was going to get me in trouble. Again when I looked at Mrs. Raven she was smiling, like she was a mind reader.
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“There’s pop in the frig, and chips on the counter. Help yourself.”
“Thank you, Mrs. Raven.”
“Avery, please, I’ll see you about twelve o’clock.”
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Mrs. Raven drove away. All there was on television was reruns. The new programming didn’t start for month. Looking at the reading material in the magazine rack, they were typical except for one. It was a catalogue from Victoria’s Secret. My boner was still semi erect and growing. Grabbing the magazine I headed to the upstairs bathroom. Mrs. Raven’s bewitching scent was strong. The clothes hamper got my attention. My four and a half inch tool was begging for relief. Opening the hamper revealed a bra and a pair of black thong panties. Feeling a little stupid, I grabbed them. The bra’s label was Victoria’s Secret. The size tag was 34D. My moms were only 34B. The bra felt so soft. Now with it at my nose, Avery’s scent really had me ready, my boner was in my other hand pumping. I dropped the bra and examined the thong. The crotch was coated with white crusty substance. As an expert of schoolyard sexual gossip I assumed it was dried pussy juice. Smelling them, it had an intoxicating pungent odor, it was exhilarating. Holding the thong close to my nose while pumping John Thomas, my climax was one of the best ever. My sperm squirted into the bowl. Now done and feeling much better I cleaned my dick with the thong and drop them into the hamper, then flushed the toilet.
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When I passed the baby’s room, the child looked contentedly sleeping after enjoying a meal from her mom’s lovely nipples. I would be contented as well. There were two other bedrooms on this floor. One had to be Avery’s. The first one I entered was obviously hers. Like in the bathroom her scent was strong. The big king-sized bed was the largest bed I had ever seen. It seemed like a lot of bed for a single woman. My imagination had her naked waving to me to join her. There was a large seven-drawer bureau against one wall. I was nosey and looked into a drawer. It was full of bras similar to the one in the hamper. They were so soft. One of the other drawers was full of thongs and bikini panties. It was apparent, Mrs. Raven liked sexy lingerie.
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My mind was wandering. It had me watch her dressing or undressing. Avery could easily become an interesting part of my life anytime she wanted. Making sure everything was back in place, I closed the drawers. After getting a coke I looked at the catalogue. As I looked at each picture, I envision Avery wearing all the sexy outfits. My boner was showing some life. The next thing I remembered was a hand shaking me.
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“Don. Wake up.”
Avery’s was standing beside me. She looked like my dream girl.
“Are you planning to buy something?”
Then I realized the Victoria Secret catalogue was open at the thongs. I could feel the heat of my blush starting from my toes. Avery was laughing softly. If she hadn’t been laughing at me, it would be considered very sexual.
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“Don’t be embarrassed Don. The majority of teenage boys like to look and dream about women wearing sexy clothing. Girls think of boys the same way. Do you like thongs?”
“I’m sorry. I should have put it away before I went to sleep. I’d planned on watching T. V. but its all repeats.”
“Yes. I know. I found the same thing for the last two weeks. How was Alishia?”
“She’s excellent. I checked on her several times and she was sleeping soundly.”
“I’ve got to feed her now. If you’d like to stay, we can talk. I haven’t been able to make too many friends since I’ve moved. You could help by telling me about the local businesses, where the churches are etc.”
“Ok. I’ll wait for you.”
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Avery left me and headed upstairs. How I would love to watch her as she fed her child, breasts and nipples exposed. It was wishful thinking. While watching television Avery reappeared with Alisha. She sat down across from me.
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“I hope you don’t mind me feeding Alishia?”
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She was going to feed Alishia in front of me! I was tingling. I was going to see her titties and nipples. Frank my best friend would never believe me. Watching in awe, Avery opened her blouse then unhooked the front of her bra. Her hands were delicate and her long fingernails manicured. I wondered how they would feel circling my hard cock. Her breasts were gorgeous. The rosy red nipples were the size of small grapes, how could her daughter manage them?
I stared like an idiot, unable to take my eyes off of Avery’s breasts. Then I heard her laugh. She was enjoying watching me watching her feed her child.
“You’ve never seen a baby being fed before?”
“No. It’s beautiful.”
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I didn’t know what to say. The sucking motions of Alishia seemed to reduce the size of her mother’s breasts. I envied that baby. What I wouldn’t give to suck one of Avery’s nipples. This time Avery must have figured out what I was thinking about.
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“You haven’t seen a breast or breast feeding before have you?”
“No. Only in pictures and none as beautiful as yours.”
“Thank you. Would you like to see them close up?”
I couldn’t believe what she was suggesting. What did she mean by close up? Would she let me sit beside her? Could my dreams come true?
“Yes. Wait till I’m done feeding Alishia.”
I would wait till hell froze over to get close and personal with Avery. She got Alishia to burp.
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“I will put Alishia back to bed. She has a fresh nappy. That feeding should hold her till morning.”
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I was nervous in anticipation. Was I dreaming or what, was I actually getting close to Avery’s boobs. There was movement upstairs. The few minutes she was gone seemed like hours. Then she came down the steps. She was wearing a wrap that had a tie at her waist. A red ribbon held her black mane in place. She looked angelic to me.
“Don. Come, sit beside me.”
John Thomas was reacting. I couldn’t believe this was happening. We were sitting so close to each other the heat from Avery’s body was transferred to my thigh. She removed the sash, her robe parted. My little tool was really hard. There was no way to disguise it.
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“Okay, Don. You can take a look now. They won’t break. You can even touch them.”
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With her robe open, I was spellbound looking at her real titties. Avery’s nipples were thick and long. It was obvious it was no problem for Alishia to latch on to them. Each one had drops of milk forming on the tip. I touched the side of one with the tip of my finger. It was soft on the outside but felt firm.
“Don. Feel one. They won’t bite.”
Avery grabbed my hand and cupped her full breast with it. It was much bigger than a handful the warmth makes my hand tingle. Getting braver, I massaged one then the other. My fingers were wet from her milk dripping from the nipples. Her milk was thick and sticky.
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“Do you want to be my baby boy, Don?”
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Does she mean what I hoped she meant. I nodded okay. She guided my mouth to her nipple. Closing my eyes I mouthed the jewel. Her perfume was evident. Starting to suck, her milk flowed down my throat. It was sweet tasting. Avery was moaning softly. Shifting our positions caused her robe to open. She was naked except for her thong. The curly hair was escaping on both sides of the narrow bit of cloth molded to her luv lips. This was the closest I had ever been to a real pussy. Avery’s hand was on my hip slowly caressing me. It felt good. When the first breast was drained of milk Avery guided me to the other. There was no way her baby could drink all the milk Avery produced. It had a sweet taste to it.
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“Don. That feels wonderful. It’s the first time I’ve my breasts drained. Alishia can’t drink all of it. It makes me feel so sexy drained. I see it has the same effect on you.”
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Her hand dropped to John Thomas, caressing him through my jeans.
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“That is quite a tool you have there. Have you used it with your girlfriends?”
“I don’t have a girlfriend.”
“Do you masturbate?”
Now, I was blushing, nodding my head yes.
“It’s nothing to be ashamed of. Since my divorce I’ve been masturbating regularly with a dildo. Do you know what a dildo is?”
“Yes. It’s an artificial cock.”
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Avery laughed softly, she was lowering my zipper. Her warm hand was under my shorts and grasping my hard cock. That really felt good. It was a lot better than when I did it myself.
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“There is nothing like the real thing. You have a nice one, Don. It feels so warm and hard. You should have a girlfriend play with you and suck you. I know you’d like that.”
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I had answered her question about girlfriends, none. The closest I had been with a girl was at the school dance. In my mind we always did more but in real life I was a complete nerd. I always broke out in a sweat when I was close to opposite sex.
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“I don’t have a girlfriend. You’re the only girl that has touched me other than my mother and that was a long time ago.”
“Do you like what I am doing?”
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Are you kidding? Avery was slowly pumping John Thomas. I had never felt anything as exhilarating in my life. As she caressed me I was enjoying the taste of her large nipple and her milk. Her skin had a distinct taste.
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“Yes. It feels good.”
“Don. I haven’t felt this good since I started nursing. I tried breast pumps but they didn’t do the job. But you sure did. I could use you on a regular basis until I wean Alishia. Would you be interested in drinking mother’s milk for a couple of months? I’ll pay you.”
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I couldn’t believe what Avery just asked me. She would allow me access to her beautiful breasts for months and would pay for it. I didn’t tell her I would do it for free. I must be the luckiest fifteen-year old in the world. I nodded yes and continued to suck.
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“Don. We’d better do something about this before you go home. It’s nearly twelve o’clock. I told your mother I’d have you home by twelve thirty at the latest. Follow me.”
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Avery was referring to my hardon. What else could she do? Following her was a pleasure. Her robe moved gently from side to side accenting her beautiful bottom. It was beautiful to watch. As we entered her bedroom, she turned on a night light. She had rolled down the bedding. What was she going to do now?
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“Lie down Don.”
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I did as instructed. Avery dropped her robe now she stood before me in her thong. It was white with a very damp crotch. Was I the reason for that? I hoped so. She sat beside me.
“Lift your hips.”
She quickly removed my shoes, socks, jeans and shorts. My cock stood proud. Avery stood in front of me and lowered her thong. It was mesmerizing view. The love lips were large and mainly bare; there was a tuff of hair on top of her crease. Moisture was very evident. I just stared.
“You haven’t seen a girl’s vagina before?”
“No. It is beautiful.”
Avery opened her legs spreading her lotus blossom. Her inner pink lips parted, her clitoris extended an inch and was the size of my finger. She lay down beside me.
“Ok Don. Take a good look.”
Avery spread her legs wide. Her outer lips were full and puffy. The view was like a magnet. I looked and studied. Avery was watching my every move. I moved my head closer and was hit with her sexual scent. I was mixed up inside. My desire overwhelmed me. I lowered my head to about four inches from heaven. The scent was strong drawing me closer. For some unknown reason I kissed the open lips. My tongue tasted the juice. Licking her got me more and more excited. Avery was moaning her hands were on my head pulling my face into her tasty treat. When I encountered the clitoris I started to suck. I could feel her hips push against my face. Juice was flowing freely. All my attempts to trap it were fruitless. My face was covered with her syrup. I could feel her body tense and Avery went rigid.
“Don. You are a natural born pussy eater. I haven’t cum as strong as that in years. You are better than my useless teat husband ever was. And I lived with him nine years. But I have to take care of you and get you home. Lie down.”
Stretching out beside her, John Thomas was the longest I had ever seen it. I knew what I should be trying to do something with Avery’s pussy but didn’t know what to do. Avery engulfed John Thomas swallowing it whole. What a wonderful feeling, my hips pumped against her mouth as she sucked me. This must be a blowjob. At school we all talked about it as if we knew what we were talking about. From this day forth I would know from personal experience. The pressure to cum was building. With my heels dug into the mattress I pushed up against Avery’s warm mouth. Cum was delivered down her throat. I watched as she swallowed. The feeling was beyond anything I could have imagined. Avery licked her lips then she kissed me. Not a mother to son type kiss, but a real boyfriend girlfriend type of kiss. It felt so good. Her lips were full and her lipstick left a pleasant aftertaste.
“Don. We had better get dressed. You have to go home. Will you be able to come and see me tomorrow morning? I will need your service again.”
She was pointing at her beautiful breasts. They pushed out from her body. Nodding yes I reached out and cupped them both.
“As early as possible. You can tell your parents you are helping me unpack. I will pay you for babysitting tonight as well.”
Shortly after that I was on my way home. Tonight there would be no need to masturbate before going to sleep. Avery had taken care of that. I wondered what tomorrow morning would bring.
I was up early showered and had breakfast. I was really antsy. It was a perfect morning. I knew that Avery breasts were waiting to be serviced. Mom wondered what had caused this change.
“What happened to you? You actually got up early and had a shower. If I didn’t know better I would think you had a date.”
Mom was smiling when she mentioned date. I haven’t even mentioned girls around her.
“Mrs. Raven asked me to come over early to help her move some boxes. She said she would pay me for helping. You know I need the money.”
“I guess it was a good thing that you took that babysitting job.”
“Yes, Mom. It may develop into a lot more.”
I wondered what mom would say if she knew what I had done with Mrs. Raven. The feeling flooded through my body.
“Have to go, Mom. I’ll see you later.”
It was nine-ten. Mrs. Raven must have fed Alishia by now. Her breasts needed to be emptied, Don to the rescue. Mrs. Raven answered the door with the first ring.
“Come in, Don. I was thinking about you.”
Avery was dressed in a robe that opened showing a very short sheer nightie. John Thomas was showing his appreciation. She led me to a sofa. Her robe melted from her shoulders. The nightie left nothing to the imagination. Then Avery pulled two little ties and stood before me naked. My anticipation heightened.
“Don. I need you to suck me again. My breasts are so sore! They need to be emptied.”
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Avery sat down and motioned for me to sit beside her. She had me lean over her body like a child and placed the first nipple in my mouth. Her milk was warm and thick. I could feel the milk draining from her as I massage her breast. She had me switch nipples. Soon she was drained. And to think I was getting paid to do this.
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“Thank you, Don. Can you come over tonight about eight o’clock? I will give Alishia her last feeding of the evening and you can have the rest.”
“I will be here. You taste so good, Avery. I love your milk. I can’t believe this is even happening. God you are beautiful.”
“Why thank you Mr. Parsons. I see you have a little problem in your pants. This morning you are going to lose your cherry.”
“Yes. I am going to teach you how to satisfy a woman with that tool of yours. You do want to learn, don’t you?”
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It was every boy’s dream to learn how to use his tool with a girl. Avery was no girl but a really beautiful woman, and she wanted to teach me how to use my boner with her.
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“Let’s go upstairs to my bedroom.”
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She picked up her robe and led me up the stairs. Her bum moved in slow motion as she walked. I could see her pussy lips and anal pucker between her legs as she climbed the stairs. What could be better than this? The bed had been made and a blanket covering the top. In the daylight the room reflected Avery. The scent of her perfume was evident. I watched her every move.
“Get undressed, Don.”
I don’t think there was a stopwatch fast enough to have timed me. Avery lay down on the bed and beckoned me beside her.
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“First lesson will be how to keep your lady happy once you get her to bed. You know that my breasts are sensitive, also my nipples and the cartilage just under them. Always be gentle, you will get more from your lady friends if they enjoy your foreplay. My earlobes are sensitive, also my neck. I like to be nibbled. You will have to test the waters on all your lady friends to find their erotic zones on their bodies. My tummy, belly bottom, pussy and rosebud are very sensitive. I like to be kissed and sucked and licked all over my body. My former husband never could figure out foreplay. I still can’t figure out why I married to him. I am going to teach you how to satisfy me. That is of course if you want to be a student of love.”
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“Oh, yes. I want to learn all about it. Will it help me with the girls at my school?”
“It will once you get them in a position of trust, when they allow you to touch them. Usually the first conquest is a girl’s breast. If you are able to make her feel wonderful with your talents of sucking and massaging, it won’t be long before she will surrender her panties to you as well. You are going to be an expert lover when you graduate from my school of new lovers.”
“I hope what you say is true. Maybe I will have enough nerve to ask Jayden to go to a movie. She has blond hair and a beautiful face. I sat behind her at school. She is the girl I think about when I masturbate.”
“How old is Jayden?”
“She is fourteen with a sixteen-year-old’s body. She has been wearing bras for two years. Many of the other girls that I know don’t need to.”
“Okay, Don. This will be your first lesson. Get between my legs. Support your weight with your arms. Is your cock lined up with my pussy?”
Avery was going to let me fuck her. John Thomas was next to her moist opening. I nodded yes.
“Lower your body and when you feel the tip enter me push hard.”
I couldn’t believe the feeling. A warm moist glove engulfed John Thomas. My hips started to hump Avery automatically.
“That’s it, Don. It feels good.”
“But I’m so small.”
“Don. It isn’t the size that counts but how you use it. You have to make sure you satisfy your partner before you cum. That is important if you want to be offered the pleasure of her pussy. Together we will make you an expert, a stud. Since this is your first time you can cum when you are ready.”
Cum gushed into Avery. Nothing I had done in my fifteen years prepared me for the feeling of my cock ejaculating into Avery’s welcoming pussy.
“Don. Thank you for your cherry. I was your first. Next time we will try to have you hold your climax off, till I cum. We can try again in an hour. Now you can make me cum with your fingers.”
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She had me lie beside her. I lay with my head on her breasts feeling her heart beat. She took my hand and put it between her legs. Avery’s pussy was soaked. My finger ran up and down her slit.
“Don. Slowly rub my clitoris. Don’t be rough. Think of it as a soft rose petal and just caress it softly.”
I did what I was told dipping into her honey pot to keep my finger moist. Avery breath started to quicken.
“That’s it, Don. Keep doing what you’re doing.”
Her breath started to get erratic, she appeared to be gasping. Then her hips rose and her body stiffened.
“Oh, Don. That was good. It’s not going to take long to make you a love toy.”
“Yes. A love toy for every woman and girl that allows you access to her. They will melt at your touch. I will want to hear about your date with Jayden.”
“But I don’t have a date with Jayden.”
“You will. I will give you enough money to take her to a movie. All you have to do is ask her.”
“But I have never asked any girl for a date or to go to a movie. I really don’t know how.”
“It is mind over matter. You’ve no confidence in yourself. After a week of lessons you will.”
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Avery pulled me to her and kissed me. Her tongue explored my mouth. I returned the favor. My hands were all over her body. My life was changing fast.
During the next three weeks my savings increased, and so did my knowledge of being a lover as well as my self-confidence. Avery was impressed how fast I was able to become an accomplished partner for my age.
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“Don. You are now ready to try your skills on a young girl. You should have the confidence to ask Jayden for a first date. What do you think?”
“I would like to try. I haven’t had a real date. I wish it could be you.”
“That would be nice but we both have to be realistic. You are welcome to come and make love to me anytime you want. But I know you are going to want to date young ladies your own age. I will expect a blow by blow accounting of your progress with every girl you date. I want to make sure my protégé’s does everything possible to make his partners sexually satisfied.”
“Do you think I will get anywhere on the first date?”
“Oh, yes. When I am done coaching you, your first date should yield a virgin pussy to pet.”
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I thought of Jayden. She had a shapely body. Her breasts always attracted me. She had long willowy legs. Considering the time I had to practice with Avery I felt I had a good chance of making Jayden happy if she agreed to a date.
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“Why don’t you call her right now? Do you know her number?”