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Chapter Sixteen: Amanda

During the third year of middle school, I began to notice Amanda Haywood. I thought she was one of the prettiest girls in my home room and her bottom was beautifully rounded. I also saw that her breasts were beginning to develop very nicely as well. Amanda had long dark brown hair, big brown eyes and a very pretty face.

Once I had set my sights on Amanda, I began my campaign to build a close relationship with her. One day at lunch time, I managed to grab a chair by her. I introduced myself and began talking to her. The next day I managed to get a chair beside her again and we talked all through lunch. By the third day, Amanda was saving a place for me and we were chatting like old friends during lunch.

I told Amanda that I thought she was the nicest girl I had ever met. Other times I would tell her that her hair was pretty or that I thought that her clothes looked very nice. Within a couple of weeks, I judged that I had progressed sufficiently toward winning Amanda over. So I decided to try and move things to the next level.

One day after lunch, I pulled Amanda aside and said, “There’s something important I have to tell you.”

Amanda asked, “What is it Bill?”

I whispered in her ear, “I can’t tell you here. You have to come with me.”

I had already scouted out a spot that was relatively isolated. In the reference section of the school library there was small corner completely hidden by tall shelves of books. After I got Amanda there, I said, “Amanda I like you a lot and I want you to be my girlfriend.”

Amanda said, “I like you a lot too Bill. I kind of thought I already was your girlfriend.”

I replied, “I was thinking that way too; I just wanted to make sure. Will you let me kiss you to prove it?”

Amanda glanced around and said, “OK, you can kiss me; but then let’s go. We could get into trouble if someone sees us.”

I pulled Amanda close to me and started kissing her; but I wanted to try for a little more. I slid my hands down Amanda’s back and began to squeeze her bottom just a little. I think Amanda was surprised by this because she pushed away from me just a bit. But I was in no mood to be deterred and I became more insistent. Amanda apparently decided to let me have my way and she let me continue to squeeze and massage her butt just a little longer while we kissed.

In time I began to develop a possessive behavior towards Amanda. When we were sitting at the lunch table I would slip a hand down to lightly squeeze or massage her thigh as we talked. I got her to go to that corner in the library with me every day and she willingly let me kiss her. I always tried touching her bottom too; but I didn’t make a lot of progress. I guessed that Amanda was too afraid that someone might see us.

I asked Amanda if she would like to come over to my house to visit. I suggested the next Saturday. Amanda said that she would like to come over; but she didn’t know if her step mom would let her. I said that I would get my mom to call and see if it was alright.

That evening I asked mom about having Amanda over and mom agreed to call Mrs. Haywood. When mom told dad about the arrangement he said, “Bill, your mom tells me you invited a girl over. What gives? Is she your girlfriend?”

I said, “No dad, she’s just a friend. I think she’s very nice.”

Dad said in a confidential tone, “You’re sure she’s not your girlfriend. After all it’s high time you began to take an interest in girls.”

I said, “She’s just a friend dad.”

Mom said, “Stop teasing him Steve. There’s nothing wrong with Bill having a friend who happens to be girl. Whether you think so or not, there doesn’t have to be more to it than that.” Dad didn’t reply; but I could tell by his expression that he wasn’t very pleased with mom’s last comment or very pleased with me.

Saturday morning mom and I drove over to Amanda’s house. Her neighborhood was almost four miles north of mine and wasn’t nearly as nice. All the houses on her street were a little shabby and rundown looking. We found Amada’s house near the end of the street.

As mom and I came up the front walk a very plump woman opened the door saying, “Hi I’m Amanda’s stepmother come on in for a few minutes.” As we entered the living room, I noticed an older girl sitting in a recliner smoking a cigarette. I guessed that she was at least seventeen or eighteen. Mrs. Haywood said pointing to the girl, “This is my daughter Cindy.”

Mom said, “I’m very pleased to meet you Cindy.”

The girl looked up, took a drag off her cigarette and said, “Yeah same here.”

Mrs. Haywood said, “Cindy put that damn thing out.”

The girl took another long drag off the cigarette and stubbed it out in an ash tray she was balancing on her lap. Cindy was a much younger version of Mrs. Haywood. She was very plump like her mother; but not quite to the point of being unattractively overweight. She was wearing a loose fitting tank top and shorts. The tank top, loose as it was, didn’t hide the fact that her breasts were very large. Her thighs were large but firm and smooth and I had no doubt that her bottom was very amply curved. Cindy had shoulder length dark red hair, big green eyes and her face could have been very attractive if it wasn’t for her dour expression.

Just then Amanda came into the room. She looked very cute. She was wearing pale blue shorts and a white blouse. I noticed that the shorts fit her bottom very snugly and the thin material of the blouse emphasized her breasts. I began to get a little excited as I thought about my plans for the day.

When Mrs. Haywood saw Amanda she said, “You couldn’t have finished cleaning the bathroom already.”

Amanda said, “I’m almost done. I just wanted to say hello to Bill and his mom.”

Mrs. Haywood said, “You’ll have time to visit later. Now get going. I’m sure Mrs. Bradley doesn’t have all day to wait for you.”

Mom said to Mrs. Haywood, “Please call me Monica.”

Mrs. Haywood said, “OK. Monica it is and I’m June.” Then she said, “You know Monica I’m the old fashioned type. I expect the girls to help out around the house.” As Amanda hurried from the room, my eyes strayed to her bottom again; it was looking unusually sexy today.

Now Mrs. Haywood was saying, “Come on into the kitchen Monica and have some coffee; we’ll get better acquainted.” To Cindy she said, “Try doing something useful. Entertain Bill for a while.”

When mom and Mrs. Haywood left the room, Cindy said, “So you’re Amanda’s boyfriend. You look awful big for middle school. Are you sure you’re not too old for Amanda?”

I said, “I take after my dad; he’s real tall and Amanda and I are just friends.”

Cindy said sarcastically, “Oh is that so. Then what were you staring at just now? It looked like you had more than a little friendly interest in Amanda’s butt. If I were Amanda, I’d be a little worried about your intentions.”

Cindy had definitely caught me off guard and she knew it. She let out a low chuckle as my face began to turn bright red. I started to say that I didn’t know what she meant; but Cindy cut me off saying, “Don’t bother lying. I know what guys want. Most of them can’t think of anything else.”

While I was still thinking of something to say, when Cindy said in a confidential tone, “Don’t worry Sport. I won’t tell on you. I won’t screw up your chance to get a cheap thrill. From the way Amanda goes on and from the looks of that car outside, I guess your folks must have some real dough. You know, I could go for you myself. I’ll bet you’d like that. I saw you trying to stare a hole through my top. Come over here Sport.” I hesitated for a moment, trying to calculate what she might have in mind. Then Cindy said in an exasperated tone, “Come on over here. I won’t bite you.”

I walked over to the recliner and stood in front
of it. Cindy looked me up and down. She seemed to be making some sort of an assessment. She took the ash tray from her lap and sat it on the floor. Th
en she said softly, “This is just to keep you from getting any more eye strain.” Before I could comprehend her meaning, Cindy quickly pulled up the front of her tank top. She wasn’t wearing a bra. I got a good look at her breasts and they were definitely impressive.

After she pulled her top down Cindy said, “Now there’s something for you to have a wet dream about. Of course knowing you the way I think I do; I’m sure you’ve got designs on getting more than a quick look at Amanda’s little goose bumps and she’ll probably let you. I know I shouldn’t spoil a surprise, but Amanda just got some new little bras last week. One of them is pale pink and I’ll bet she’s wearing it for you today. I think she might be wearing pink panties too. But don’t think about that too much. You’ll probably cream in your shorts. And don’t go getting all macho and don’t rip Amanda’s bra off. Let her unfasten it for you. Those little bras are nearly as expensive as the real ones. And one more thing; don’t try to get too lucky today. If my little stepsister turns up pregnant, we’ll know who to sic her dad on.” Cindy chuckled again as she lit another cigarette.

A short time later mom, Amanda and Mrs. Haywood came out of the kitchen. Mrs. Haywood was saying to Amanda, “Have a nice time and be good.”

As I joined mom and Amanda at the front door Cindy said, “Yeah, you kids behave yourselves. Don’t do anything that I wouldn’t do.”

As the front door closed I heard Mrs. Haywood saying, “Put that damned thing out. You’re stinking up the whole house.”

As we drove away Amanda said, “This is a very nice car Mrs. Bradley.”

Mom said, “Thank you dear. I don’t know much about cars; but my husband says that this model is very reliable.” I was surprised that both Cindy and Amanda had commented on mom’s car. It was just a plain old Lexus and at least two years old.

When we got to the house I could tell that Amanda was very impressed by everything. See kept looking around as if she couldn’t take it all in. Mom started fixing us some lunch.

Amanda asked, “Is there anything I can help you with Mrs. Bradley?”

Mom replied, “No thanks dear. Enjoy your visit with Bill. I have everything under control in here.”

I took Amanda out to sit on the patio. Amanda said, “Bill you are so lucky. This street is beautiful and the houses are almost like mansions. I think your mom is really nice too.”

I said, “Your stepmother seems very nice; but I think your stepsister is a little strange. Why didn’t you ever mention her?”

Amanda said, “June always acts nice around strangers, but it’s just an act. I don’t like Cindy very much and I don’t think she likes me. We’ve never got along very well; that’s why I don’t talk about her.”

Then I asked, “What about your dad?”

Amanda replied, “Dad’s OK. He drives one of those big tractor trailer rigs. He’s an independent trucker and on the road a lot of the time.”

I asked, “What happened to your mom?”

A far away look came over Amanda’s face and she said, “My mom left dad when I was still little. I can barely remember what she was like. One of dad’s sisters took care of me for about a year. Then dad married June. Sometimes I think dad married her just to get someone to look after me. When he’s home, he doesn’t even act as though he likes her very much. I know he can’t stand Cindy.”

Amanda and I continued to chat until mom called us in to lunch. When we entered the kitchen mom said, “There’s soup, salad and sandwiches for you two and some homemade chocolate cake for desert.”

Amanda asked, “Aren’t you eating with us Mrs. Bradley?”

Mom said, “I’d love to; but I have a Library Friends committee meeting and I’m afraid it’s going to be a long one. Now you two enjoy yourselves and I’ll be back in about three hours.” Mom’s committee meeting wasn’t just a lucky coincidence. I had planned things that way.

As Amanda and I sat down to eat, we heard mom’s car pulling out of the drive and I said, “Well it looks like we have the place to ourselves.”

Amanda asked, “Where’s your dad?”

I replied, “Dad checks in with his clients most Saturdays. He won’t be home until late this evening.”

We ate mostly in silence. It felt nice, just Amanda and I being alone together. Occasionally I would glance her way. She was a very pretty girl and I liked looking at her. When we finished lunch I said, “Let’s go up to my room and listen to some music.”

I got up from the table and Amanda said, “Wait a minute Bill. We can’t leave this mess for your mom. You show me where things go; I’ll wash the dishes and straighten the kitchen.”

I said, “We’ll do it together.”

After we finished in the kitchen, Amanda followed me to my room. When we went into my room Amanda looked around for a while and said, “Bill this is almost too good to be true; your own computer, a TV with a home theater system and a private bathroom. What more could you possibly want? This room is perfect.”

I said, “It’s perfect now because you’re in it.” I looked at Amanda and held out my arms. She came over to me and we kissed. As soon as we started kissing I felt myself getting very aroused. After we had kissed for a while, I moved my lips lower and began gently kissing Amanda’s neck. I could hear Amanda’s breathing becoming more intense as I continued to kiss her. I moved a little lower until my lips were just above the top button of her blouse. Then I began to unbutton it. When I had finished with the last button, I gently pushed the blouse open and saw that Amanda was wearing the pale pink bra. I kissed all along the top of Amanda’s bra. Then I raised my hands and pushed the bra up. Amanda’s little breasts slipped out of the cups and in a moment I was holding them in my hands and lightly sucking on her taut nipples.

As I continued give my full attention to Amanda’s breasts, I could feel my tool becoming stiff and it seemed that Amanda’s level of excitement was as great as mine. I moved my hands around and began to massage her back slowly moving them lower. When I reached the waistband of Amanda’s shorts, I slid my hands down inside her shorts and panties and began to massage her firm rounded bottom. I felt Amanda stiffen a little and start to push away from me. Keeping my hands on her bottom, I pressed her closer and began kissing her lips again. She seemed to relax a bit and as we continued to kiss, I cupped her bottom cheeks and gently squeezed them. Then I said, “Amanda there’s something I’ve wanted to do.”

“What’s that Bill?” Amanda asked a little breathlessly.

“Well, I’d like to spank your bare bottom,” I replied.

Amanda seemed a little confused and she asked, “Why would you want to do something like that Bill? Why would you want to hurt me?”

“I don’t want to hurt you Amanda. It’s not like that at all. I just think spanking a girl’s bare butt is very exciting. You just might find that it’s a turn on for you too. Haven’t you ever been spanked?”

“Sure, when I was little. June used to spank me and Cindy when we got into fights, but I sure didn’t think it was a turn on. It just hurt.”

Then I asked, “Please can I do it anyway? If you don’t like it I’ll stop.”

Amanda thought about what I had said for a while and then she said, “Well if you really want to; I guess it’s OK. I think I can trust you. What do you want me to do?”

I went over to the computer desk, pulled out the chair and sat down. Then I told Amanda to get across my knees. Amanda came over to the side of the chair. As she got into position across my lap she laughed a little nervously and said, “You know Bill I feel a little silly doing this. I’ve had a little experience with other boys; but none of them ever wanted to spank me.”

I didn’t reply. I was too busy getting Amanda’s sexy butt positioned across my knees. Even before I began to take Amanda’s shorts and panties down
my pulse was racing. I had been dreaming about seeing her sexy little butt for a long time and the outline of her beautifully mounded bottom cheeks
beneath her shorts and panties had me trembling in anticipation. I slid Amanda’s shorts down over her thighs and saw that Cindy was right. Amanda was wearing pink panties. I ran my hand over her bottom and just the feel of it through the thin silky covering of her panties made my stiffened tool throb. My hands were trembling as I began to slide Amanda’s panties down to slowly reveal her perfectly formed bottom. There was no doubt in my mind that Amanda’s butt was made for spanking. Her bottom cheeks curved up enticingly and I had no doubt that they would be very firm and resilient. I applied a couple of light swats to each bottom cheek and my expectations were more than met. Amanda’s little butt was exceptionally springy. Her exquisitely mounded bottom cheeks bounced back beautifully after each swat. I now applied myself to warming her butt thoroughly. I brought my open hand down sharply into the center of Amanda’s bare little seat several times in rapid succession and the resultant CRACKS were music to my ears. Then I began to shift my attentions alternately from one bottom cheek to the other. In short order I had Amanda’s bottom coming up to a light pink hue.

As I continued to spank her sexy butt, Amanda began to move just a little on my lap and then she began to say “Ouch!” with each successive swat. However she didn’t tell me to stop. So I continued the spanking for a little longer before I stopped. Amanda’s butt was bright pink now and I ran my hand over it appreciatively. I slid a finger down between the backs of Amanda’s legs and sought out her love nest. When I encountered her sweet little fuzz covered slit, I slipped my finger in and found it warm and very moist. Amanda’s clitoris was beginning to stand to attention and I began to toy with it; lightly running my finger around and over it. My mind was already racing ahead to plans for getting Amanda on the bed so I could explore her sweet little pussy more thoroughly. I could tell that I was bringing her to a high state of arousal and decided to try for a bit more. I let a finger of my free hand slide down into the cleft between her bottom cheeks to contact her puckered little bottom opening. I began to gently probe there when things suddenly went very wrong.

Amanda reached around and slapped my hand away and in the next moment she was up off my lap quickly pulling her shorts and panties back into place. I asked, “What’s the matter Amanda? What’s wrong?”

Amanda began to adjust her bra and button her blouse as she said, “That’s enough Bill. You’re going too far too fast for me.”

I was puzzled and said, “I don’t understand. I thought you liked what we were doing.”

Amanda replied, “Bill you have to understand, it took a lot for me to let you do the things you were doing just now. I guess it might not be any big deal to some girls; but it’s different with me. Don’t get me wrong; I liked what we were doing. I liked it a lot; maybe even too much. I can tell you’ve had some experience with other girls and that’s OK. Maybe they let you do whatever you wanted; but it can’t be that way with me. Not until I’m ready. I want you for a boyfriend; but I’m won’t be like Cindy. I made a vow to myself about that. Cindy has lots of boyfriends; but only because they know she’ll let them do almost anything. So there it is. You don’t have to bother with me anymore if you don’t want to. I’m probably not the right kind of girl for you anyway.”

What Amanda said made me think and I didn’t like myself very much as a result of it. Amanda was a very nice girl and I liked her a lot; but in reality my main goal had been to get what I wanted. I said, “I’m really sorry Amanda. You’re very special to me. You should know that. I just got carried away because you’re a very sexy girl; but you do mean more to me than just that. Just give me a chance to prove it.”

Amanda said, “I hope you mean that Bill. I want to keep being your girlfriend. You’re the first boy I’ve ever really liked and I want to please you. When it comes to the other things; don’t think I’m a cold fish, because I’m not. It’s just that I’ve never done anything quite like that before and it’s going to take a little time and more trust building for me to get comfortable with that side of things. Don’t push it and everything will work out.”

I went over to Amanda and put my arms around her. I gently pulled her toward me and kissed the top of her head. She looked up at me and we kissed again. Then I said, “You’re wrong about one thing.”

Amanda asked, “What’s that Bill?”

I said, “You’re just the right kind of girl for me.” Amanda smiled and I said, “It’s too nice a day to be cooped up in the house. Let’s go for a walk. I’ll take you on a tour around the neighborhood.”

Amanda said, “It sounds nice. I’d like that.”

When I think back over the events in my life, most of which were admittedly sordid, there were a few shining moments. My walk with Amanda that afternoon was one of them. It was a beautiful fall day and unusually warm for the time of year. The leaves on the huge old oaks and maples that lined the street were beginning to turn colors and the smell of freshly cut grass permeated the air.

We ambled along holding hands and talking. I was feeling happier than I had in a very long time and I knew it was because I was with Amanda. She was an extremely interesting and intelligent person and we had a lot in common. I also found out that Amanda was having a birthday the next Sunday. I made a mental note of this for future reference. Most importantly, I was discovering that it was possible to be with a girl and enjoy her company without continually scheming on some way to get her panties down.

As we approached the end of the street, we passed Heather’s old house. I spite of everything; I felt a twinge of excitement as I remembered my experiences behind those walls. Within seconds I found my gaze drifting down to Amanda’s bottom as she walked beside me. It took some will power, but I shifted my gaze back to her sweet face and banished other thoughts from my mind. This was a lot easier than I expected and I think it lulled me into a sense of complacency regarding the flexibility of my basic character. With Amanda at my side, I truly believed that I could become a different person. At that time I didn’t know that I would soon be coming to a fork in the road and that my new resolve wouldn’t stand the test.

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