The introduction is a bit long but necessary.
It all started when I was in the second grade, 7 years old. The end of the school years was approaching. Early one morning i walking to school earlier than normal, because I had volunteered to help my teacher with a project. My school was about six blocks from home. As I neared the end of the second block I saw someone crossing the road ahead of me. I quickly recognized them, it was Debby, one of my classmate's who had also volunteered to help our teacher. Debby was one of the cuter girls in my class. She had sandy blonde hair and bright blue eyes. She was taller than many of the girls in my class. She had a wonderful smile. We were not close friends, but she was very friendly when we interacted. She seemed to be happy most of the time. We got along well.
She made no acknowledgement that she had seen me. She continued walking slowly toward school. As I approached her I could hear her softly sobbing. I caught up with her, slowed down my pace, and walked beside her for several seconds. She was sniffling trying to avoid crying.
“What’s wrong Debby?”, I asked.
It took several seconds but then sniffling and stuttering she said, “M.my parents had a big fight l.l.last n.n.night. I think they are going to get d.divorced. My f.father was so m.mad he left and didn’t c.come back. This morning my m.mother would not talk ab.bout it.”
All I could think to say was, “I am sorry Debby.”
I put my arm around her and she slowly put her head on my shoulder. She continued lightly sobbing as we walked to school.
“Maybe things will be better by the time you get home,” I tried to comfort her.
“Thanks Andy,” she said as we entered the school.
We went to our classroom and helped our teacher until school started. I noticed throughout the day that Debby was not her normal self. She was quiet and just looked sad. We hadn’t finished our project in the morning, so Debby and I stayed an extra 15 minutes to finish. When we finished our teacher thanked us and then Debby and I walked out together.
After we got away from the school building and away from any prying eyes, Debby asked me to hold her again. Soon we were walking with my arm around her and her head on my shoulder. She started crying softly as we walked on. I held her a little tighter and she seemed to appreciate it.
“I hope things are better when I get home!” she said sniffling.
We walked slowly to her house, it was just one block over from mine. When we arrived she stopped, gave me a hug, and then a hard kiss right on the lips. I had never kissed a girl before, except maybe a relative.
She then gave me a squeeze and said, “Thank you! See you tomorrow.”.
After that she walked up to her house and went inside.
I just stood there for a bit thinking about what had just happened. I walked the rest of the way home puzzled, but feeling good about it. I kept thinking about it off and on all night. Finally I went to bed and did not give it another thought until school the next day.
I was one the first to arrive and waited at my desk for everyone else to arrive. When Debby came into the classroom she looked at me then quickly turned away. She gave something to our teacher, then she hurried to her desk and sat down staring straight ahead. I wondered if I had done something wrong. I felt so bad for her. Things must not have improved.
Debby was again quieter than normal throughout the day. She had that same sad look as the day before. She avoided me at both lunch and recess. At the end of the day when the bell my teacher asked me to take some paperwork down to the office. I noticed it had Debby's name on the outside of the envelope. I wondered what was in it while I walked to the office.
It was nearing the end of the school year, so the office was busier than normal after school. It took several minutes before Mrs. Anderson, the receptionist, was able to take the envelope from me. She thanked me, I left, and went out the nearest outside door. To my surprise Debby was waiting just outside.
“Can you walk me home?”, she asked.
“Sure, I would be glad to!” I answered a little puzzled.
As we left the school grounds, Debby moved closer and put her head on my shoulder. I instinctively put my arm around her and hugged her lightly. We walked along slowly, silently for several minutes.
“Are things better today?”, I finally asked, not really knowing what to say.
“No not really. They are worse”, she replied. “My dad is moving to a city near Chicago. Mom says I am going to live with him. She has too many things to work out here.”
I learned several years later that Debby's mother had gone somewhere to be treated for alcoholism. Debby’s dad had threatened to go to court to have her mom’s parental rights terminated if she did not get help. Also that Debby’s father was being transferred by his company to Chicago to be the head of the division there.
“My dad and I are leaving at the end of the week since that is the last day of school,” Debby continued. “Only two more days to pack and say my goodbyes.” She started choking up, so I squeezed her a little harder. “Can I write to you?” she asked.
“Sure! I would love to,” I responded without hesitation.
“Thanks! Write down your address and give it to me tomorrow after school,” she said.
“Ok,” I said.
By this time we were nearly at her house. Just as yesterday she moved in front of me, gave me a big hug, and a longer, harder kiss than the day before.
“Thanks, see you tomorrow,” she said as she turned and walked up to her house.
“See you tomorrow,” I replied.
Again I walked home thinking about the hug and kiss. I was having feelings that I had never experienced before. It was kind of like the feelings I had for my sisters and brother, but it was not quite the same. My mind was gyrating all night. I didn't sleep well. I woke up several times thinking about Debby and then feeling sad that she would soon be gone.
The next day Debby did not show up at school. After school I walked to her house. She was sitting on the front steps. When she saw me she jumped up, ran to me, and gave me a hug.
“I hoped you would come by. I needed someone my age just to care about what I was going through. I had to stay hone and pack the stuff I wanted to take with me. Did you write down your address for me?”, she asked.
I handed her the sheet of paper on which I had written my address.
“Debby, I am going to miss you,” I said. “I wish we had gotten to know each other better. I wish we had more time together, to get to know each other.”
“My dad is picking me up when school let’s out tomorrow. I will give you my goodbye now,” she said. She hugged me and gave me a big kiss. I hugged and kissed her back, no longer surprised at her actions. “I will miss you too. Don’t forget to write back,” she said with tears in her eyes. She turned and went into her house.
I felt very sad as I finished my walk home. I thought about Debby the rest of the night, but finally fell asleep sometime after midnight.
The next day at school it felt weird every time I looked at Debby, knowing this might be the last day I would ever see her. I felt sad every time I thought about it. The day went by too quickly. Being the last day of school there was no real classroom activity. The bell rang. Our teacher wished us a good summer. Everyone left the classroom. I followed as Debby walked to the front door. It was not the normal door I would use to leave. She walked out the door. Her father was waiting for her in a car with a small trailer attached. Debby got in the car, then looked over saw me and waved. I waved back as the car pulled away.
I walked home slowly and sadly. Usually the last day of school was a happy day, but this one was not. I was feeling sadder by the moment. I had not been close to Debby until the last few days, but I was feeling a great sense of loss.
The next week I was busy with summertime stuff. On Saturday I received my first letter from Debby. She said she was doing fine, but she missed her home and she missed me. She went on to describe the apartment she and her father were living in and the city. But she said again that she missed home.
I wrote back describing my plans for the summer, swimming lessons, little league baseball, and a family vacation to the Black Hills, the Bad Lands, and Mount Rushmore. I closed by saying I missed her too.
We wrote back and forth about every month or so. During the summer she wrote about her gymnastics classes, and her father and her looking for a house. She described downtown Chicago and the waterfront on Lake Michigan. She ended every letter by saying missed me.
When school started she described her teacher and classmates. She said it was hard being the new kid. A lot of the kids were different than back home. Many were rude and some were crude. She did make a few friends and hoped things would get better.
I wrote her about my class. Most were the ones we had gone to school with in the 1st and 2nd grade. There were a couple new kids that had just moved into the neighborhood. They were welcomed by rest of us. I told her that I missed her very much when I closed the letter.
Our letters continued for about 4 or 5 years, but eventually the time between letters got longer, then they stopped altogether. I never got a response from one of my letters, so I wrote another. After a few weeks I still had not received a reply from Debby. I still got a card for my birthday. I sent her one for her birthday.
I got a paper route the summer before my 13th birthday, that included both my house and Debby’s old house. Aside from delivering newspapers, one of my tasks was to collect money for the newspapers I delivered. I had to do this every two weeks. On my first round of collections I walked up to Debby’s old house. I didn’t even know if Debby’s mother still lived there. I rang the door bell. Debby’s mother answered.
I said, “Hi, I am your new paperboy. I am here to collect for the last 2 weeks deliveries.”
She brought me the money and gave it to me. “Weren’t you in school with Debby before she left?” she asked.
“Yes I was. How is Debby doing?” I asked.
“She is doing well. I will be going to see her next week. I can say hello for you?”
“Sure,” I said. “Thanks for the money and the tip,” I said as left.
As I walked away I thought about how much Debby and her mother looked alike. Same sandy blonde hair, bright blue eyes, same very pretty face. Debby’s mother also had long legs and large wonderful breasts. Being 13 I had just started noticing them, ok becoming obsessed with them.
Two weeks later when I was out collecting, Debby’s mom told me that Debby said hi and had asked how I was doing. After that we didn’t talk about Debby when I came collecting.
Moving ahead 2 years. I had just turned 15 and starting the 9th grade in a couple of days. I had not received a birthday card from Debby. I was very disappointed and wondered if I would ever hear from her again.
The first day of school I went to my homeroom and showed my teacher that I had a problem with my schedule. Somehow I had been scheduled for 2 classes during fourth period and no class during fifth period. The teacher sent me to the office to get things straightened out.
I waited in the office with several other students that had scheduling problems. I was told I was number 18. As I waited some students came in and asked for a copy of their schedule. I did not recognize any of them, so I assumed that they had just moved into the school district. Then in walked a tall sandy blonde haired girl. Her back was toward me as she approached the receptionist's desk. She had long slender, beautiful legs. She asked for her schedule, received it, and turned around. As you probably have guessed, it was Debby.
She noticed me at the same time I recognized her. I stood up as she walked over to me. She looked so much like a younger version of her mother it was almost frightening. In the few moments it took her to reach me, I noticed that she had good sized breasts because they bounced a little as she walked. Debby grabbed me in a very strong hug and gave me a very passionate kiss. I felt some stirring between my legs.
“That is not appropriate behavior in school! Young lady you need to get to your class!”, the receptionist warned.
We both said sorry and backed away from each other.
“Meet me at my house after school,” said Debby as she walked toward the office door. I nodded yes as she walked out. I felt more stirrings between my legs.
The receptionist called my name to see my counselor. I got my schedule straightened out and headed to my class. I had hoped that by luck I might have a class with Debby. The day went extremely slow. I couldn’t wait to see Debby later. Sixth period really dragged. When I got home I quickly finished my paper route leaving Debby’s house for last because it was near the end of a block.
She was sitting on the steps outside waiting for me. I walked up to her and took a good long look at this extremely beautiful and desirable young women. She patted the step next to her. I sat down next to her. We sat saying nothing for a minute or so.
“You forgot to do something,” Debby whispered. It took a couple of seconds, but then I reached over and put my arm around her. She laid her head on my shoulder. I hugged her close. “My father died of a heart attack a little over a week ago,” she whispered before starting to cry. I tightened my embraced as she sobbed and shook.
“I am so very sorry,” was all I could think to say.
She shifted closer and I put both arms around her and pulled her close. She continued to sob in my arms for several minutes. I could feel her breasts up against my chest and the wetness of her tears on my back. In another situation I would have gotten aroused quickly.
“I.I h.have moved b.back with my mom,” she stated as she regained composure.
“I am sorry about the circumstances, but I am very happy to see you and hold you again,” I said.
Her mother came to the door and paused apparently a little surprised. She waited for several minutes, until she told Debby that it was time for supper.
“Would you like to have Andy join us?” her mother asked.
“Y.yes, that would be great mom,” Debby answered.
Debby’s mother went back inside. Debby gave me a big kiss then stood up. We went inside and I called home. I told my mother I wanted to eat at a friend’s house. My mother agreed.
Dinner was relatively simple, sandwiches and home made macaroni and cheese. As we ate Debby looked at me and smiled.
“So you and Debby are pretty good friends?” she asked, but it was not really a question.
“Yes mother. He is the one I wrote to while I was in Chicago,” Debby said.
“Well I approve. He makes you smile. He is good looking,” her mother said. I blushed.
We finished dinner. I helped clean up. I gave Debby a quick kiss and left. I walked home excited and wondering where things would go with her. I made her house my last delivery as a regular thing and we sat and talked each day. This went on for over a week. One night I told her I would be back to collect for the deliveries later that night just before her mother called her in for supper. She smiled back with a smile I hadn’t seen from her before.
Later that night I was collecting from the houses on Debby’s block. As I was going from one house to the next a car going down the street stopped beside me the passenger window went down. Debby’s mother leaned over and said, “Debby said you would be collecting tonight.
"I am going out for the night so I left the money with her. I think I was in Chicago dealing with things there last time you tried to collect. I think I owe you for four weeks, right?”
I told her she was correct and wished her a good night and she drove off.
I continued until I arrived at Debby’s house. I knocked on the side door and Debby answered. She smiled that same devious smile she had earlier. She asked me to step in and she would get my money. I stepped in to the kitchen and Debby disappeared through a door and around the corner. After she left the room I heard a few noises from beyond the door. A few seconds later I heard her footsteps approaching the door she left through. I was puzzled when she came around the corner. Debby was now wearing a bath robe instead of the shirt and pants she was wearing earlier. She struck a sexy pose in the doorway. The robe came down to just above the knees. It was tied at the waist. The neckline came down in a V, not exposing much but allowed me to see that she was not wearing the shirt she had on earlier.
She noticed my puzzled look and giggled as she said, “You are going to have to go on a treasure hunt to find your money.” Then she waved one of the ends of the tie toward me. I was a little slow in understanding what she was implying, so she tugged lightly on the tie.
Finally getting the hint I walked over set my receipt book on the table, then unfastened the tie for her robe. Her robe opened down the front allowing me to see she was only wearing a lacy bra and matching panties underneath. There was a corner of a dollar bill peeking out from her right bra cup. Although I could not see much more because of the robe, my penis started to respond. Her breasts were a large as I imagined them to be. I stared enjoying the view very much.
“Go ahead take it!” she demanded almost begging. I reached my hand to take the bill. I grabbed the corner to pull it out. She grabbed my hand and said, “You should check to see if you want anything else in there first.”
Now catching on I reached inside her bra cupped her breast with my whole hand. She let out a soft moan. As I began to massage her breast the dollar bill floated to the floor. I lightly squeezed her breast and my fingers searched for nipple. When the search was successful I lightly circled her nipple with my index finger. “Mmmm … ahhh,” Debby moaned to my touch as her head tilted back. I then touched her nipple lightly she jumped slightly and let out an “oooo”. Her nipple was erect and hardened as I ran my finger across it. My penis continued to swell toward it's full size.
“You should continue your treasure hunt. Maybe there is something in the other side,” she encouraged.
I reached my other hand up, not wanting to remove the first from it's “treasure”. I reached under her left bra cup found another bill “hiding” there. Soon it joined it's friend already on the floor. I went through the same procedure on her left breast. With the same oooo’s and aaahs coming from Debby’s lips. My penis was now almost full size.
“Time, aah, to continue on,” she whispered.
I removed my right hand, but left my other hand in place. I started caressing between her breasts and started moving down toward her stomach thinking I was going down to her panties.
“No move to my back first,” she implored.
I realized she had planned this down to the last detail. My hand reached around her following the fabric of her bra. Toward the middle of her back my fingers encountered another piece of paper. Another dollar bill was folded around the hooks for her bra. It quickly joined it's partners on the floor. For a couple of seconds I fumbled with the hooks of her bra. I realized that unfortunately I would have to take my left hand from it’s place inside her bra cup. I removed my hand after a light pinch of her left nipple. Debby jumped a little and let out another “oooo”. My left arm wrapped around her with my left hand joining my right at the bra hooks. I had never hooked or unhooked a bra before. Debby giggled as I fumbled around for a few seconds.
“I am glad you don’t have any experience with unhooking bras”, she giggled again.
It was more difficult than I thought it would be. However after I got the first one unhooked the remaining 3 came swiftly after. Debby had moved closer to me during my struggles.
“It feels like somebody is getting excited,” she whispered in my ear. I had not noticed that my member was pressing my pants against her panties.
“Yes I am,” I replied. “You are so very beautiful. How can I help but be excited.”
I reached up to slip the bra straps off her shoulders. Again she stopped me by saying, “Your treasure hunt is not over. Move your hands lower.”
My hands moved down caressing her back with my fingertips as they traveled her spine. She purred as I did this. Soon my fingers reached the top of her panties. I barely hesitated before pushing them under the waistband toward her butt cheeks. There was another bill on each cheek. I pushed them through the leg holes in her panties letting them fall to the floor. I grabbed her rear end and pulled our bodies together. My penis was crushed between our bodies, only my clothes and her panties separating it from her vagina. I could feel the heat radiating from her. Debby moved her body up and down against me taking my penis toward it’s full hardness.
It was then I could tell she had something in the front side of her panties because I heard it crinkle. I brought my right hand around to the front. I found another bill there covering her pubic hair. I pushed the bill down through the leg hole in her panties. My fingers grazed her vaginal lips in the process. She moaned again. I noticed the bill was damp and my hand felt the heat emanating from her.
I started to pull her panties down but again she stopped me and said, “Wait I don’t want my mother to find anything out here. You pick up the money and follow me to my bedroom.”
I picked up the six bills from the floor and put them in my pocket. I retrieved my receipt book from the table and followed her to her bedroom.
Once inside I started to close the door.
“Leave the door open. In case my mother comes home early I want to hear her cone in!”
She had definitely put some thought into this. She pulled the shades down. Her window faced the street. She came over to me and pulled my t-shirt over my head. I pulled the robe and bra straps off her shoulders and let them drop to the floor. This was the first time I had seen a woman topless, except in pictures. Debby’s breasts were perfect. They were round and perfectly shaped. I believed that they were a small C cup size, this was later confirmed by seeing the tag on her bra. Her skin was lightly tanned. Her areolas were tan. Her nipples were pronounced and pink. She smiled as I appreciated her breasts with my eyes.
“Not done yet,” she said as she unbuckled my belt, unzipped my pants, then pulled them with my underwear to my ankles.
My penis popped out and up. Debby stared and gasped when she saw it. I was not super long, but I was fairly big around. I pulled her panties off her hips and let them fall to the floor. I kicked off my shoes then stepped out of my pants and underwear.
We stood looking at each other for a few minutes. “Andy I have never done this before,” she said hesitantly.
“Neither have I,” I assured her.
“My mother put me on the pill. She got pregnant when she was young,” she said. “She does not want that happening to me. So we do not have to worry about that.”
I never would have thought of that, but was glad she told me. I moved to her and gave her a hug. Having her breasts pressing into my chest and my penis pressed against her pubic hair and pointing up toward her bellybutton, sure felt wonderful. I kissed her on her shoulder and neck. She returned the favor. Our mouths then met in a deep passionate kiss. Her lips opened and her tongue pressed for entry into my mouth. I opened my mouth and our tongues intertwined twisting and turning in the confined space. I inserted my hand between us and placed it on her breast. She drew in a deep breath and shuttered. I gently massaged her breast and I moved my other hand around toward her pussy. Her hand moved down toward my penis. She grasped and started stroking my penis, just before I reached her vaginal lips.
“It’s pulsing with every heartbeat,” she said.
“I have never been this aroused,” I responded.
I pushed a finger between her vaginal lips and began rubbing it up and down from top to bottom. My fingers went a little farther up on one stroke. Debby shuttered, her knees buckled, and let out a loud moan. My hand became wet as she collapsed into me pushing us unto her bed.
After situating ourselves on the bed we ended up facing each other. Debby still had a hold of my penis and I still had her breast in one hand and my other hand between her legs. I found her clitoris again at the top of her vaginal lips after moistening my fingers with her juices. I was very careful to only use a gentle touch as I circled my finger around. Debby was squirming and moaning as I continued to stimulate that sensitive spot. She was still busy stroking my shaft up and down. I lowered my mouth to the nipple that was most easily available. My tongue circled around her nipple and then licked her nipple with my tongue moving slowly over her hard nub. Debby squirmed more and moaned loudly. Her speed on my hard on increased. As I took her nipple into my mouth and started sucking her breathing became more rapid.
“K.keep doing w.what y.you are d.doing. I I … oooh y.yes … oooh y.yes,” she stammered.
Her body arched and trembled. She drenched my hand with her juices. She shook and writhed for the next minute or so. Her hand continued squeezing and relaxing on my penis as she continued to pump. My testicles tightened and I shot my load about midway through her orgasm. My jets landed mostly on her chest and face.
After her orgasm subsided she licked some of my juice off her face. “Salty but I like it,” she said.
I pushed my fingers into my mouth. “Sweet and tasty,” I said.
I moved to get out of bed. “We are not done yet,” she commanded as she pushed me back down on the bed.
My penis remained hard and stood straight up, still pulsing with each heartbeat. Debby moved over me, straddling me. She pointed my penis toward her vaginal opening lowering herself until my penis touched her vaginal lips. She rubbed the tip from top to bottom along those soft velvety lips several times. I was in heaven. She stopped at the top and pushed the tip of my penis against her clitoris. She trembled and sighed with a deep satisfaction. She moved my penis in circles around her clitoris. She continued with “ooo‘s”, “aaah's”, and “mmm’s”. I reached up and grabbed both of her breasts with my hands. Debby jerked up slightly my penis slid down her lips. When she pressed back down I slipped into her vagina just past the head of my penis. Debby and I both expressed our pleasure. Debby’s vagina was very tight, but I pushed my pelvis up off the bed to go deeper into her. Even though she was tight I easily slid farther into her because of how wet she was. She was moving her hips around to get the full benefit of the intruder inside her. She then pushed down until my penis met with resistance. Her hymen was still in place. I eased my pelvis back down on the bed pulling slightly out of her.
Debby implored, “No, keep going!” She pushed down harder on me. I pushed back. She pushed down harder. It felt like something inside her was slowly tearing. I could tell that Debby was in some pain. With one more small push I broke through and I was fully buried inside her. She yelped loudly in pain.
She held still and said, “Don’t move! The pain is going away quickly.”
We held still for more than a couple of minutes, before she started moving up and down. Slowly and cautiously at first. I began to massage her breast with one hand and moved the other one had down to her clitoris. The sensation was indescribable. We both began panting as she increased the pace. With each down stroke Debby grunted “aah”, “ooh”.
After a few minutes I felt Debby stiffen and she clamped on my penis like a vice. Her orgasm caused me to climax shooting jet after jet of sperm inside her.
Debby shook and shuddered for about a minute saying, “Oh my God!” over and over again. Then she collapsed on top of me. I reached around her back and hugged her firmly until she regained her normal breathing. I caressed her back causing her to smile. I slowly softened inside her.
Debby rolled off onto her back. “Wow, that was so wonderful. So, so wonderful.” We lay there for several minutes returning to normal.
Finally I spoke and said, “I don’t want to, but I need to leave.” We turned toward each other and kissed a long deep kiss. I got out of bed and dressed.
“You were so wonderful. I never felt anything like that before,” I said giving her one last kiss. “Promise me that we will do this again.”
“You can count on it,” she said.
She lead me to the door. I walked down the driveway and toward home.
