Chapter 1: Sexual Awakening

Hi, my name is Jennifer but everyone calls me Jenn. I was born in a small town in Indiana in 1950. What I want to recount to you here are some of the sexual experiences I have had over the years that have made me the woman I am today.

My story starts on the first day of my summer vacation in June of 1964. I had just turned fourteen in May and was looking forward to the long lazy days ahead. My parents both worked which left me home alone most days. We lived on a small farm about a miles walk from town. We weren't farmers. We didn't raise any animals, except for our dog, and the only garden we had was a small vegetable garden. My father was a regional sales manager for a large automotive parts company so he traveled a lot and my mother sold real estate.

My mother started working three years earlier so this was to be my third summer of being left on my own during the day. Only this summer I wouldn't be alone. Bobby was going to be staying with us all summer. Bobby was the son of close friends of my parents. His father was in the military and was on overseas assignment for six months and Bobby's mother had to go to summer school at an out of state college to finish up her degree. Bobby didn't want to spend the summer in a strange town with his mother so my mother said he could stay with us.

I had known Bobby almost all my life but we weren't friends. He was two years older than me and had always treated me like I was in his way.

Each morning before my mother left for work she would leave me a list of chores I had to do before she got home that night. It was mostly house work, cleaning the kitchen, doing laundry, dusting and vacuuming, and that sort of thing. I was also responsible for keeping the upstairs bedrooms clean. It wasn't as thought my mother was a slave driver. I didn't have much work to do on any given day and I was usually done with my work by ten o'clock in the morning.

For me this summer was beginning differently than the previous two summers. First of all because of Bobby living with us but also because a lot had happened to me over the last year. For one thing I had grown breasts since then. Last summer I had two very small bumps starting. Most of the other girls at school already had breasts. I was a bit of a late starter, but over the last year my breasts grew rapidly. Now my breasts were nearly the size of oranges. Another big event of the last year was that I had my first period. It started at school. Luckily my mother had prepared me for what would happen so I had a sanitary napkin in my purse.

I was a bookish kind of kid. I spent most of my summer days sitting on the porch swing reading. Sometimes a friend would call and I would walk into town and we would go have an ice cream or a soda at the drug store. Other than being aware of the obvious changes in my body, at fourteen I was very naive about sex and sexuality. I knew that sex was something men and women did but I thought it didn't happen until you were married, unless you were a very bad person, and I didn't exactly know what having sex meant. In the sixties in Indiana you weren't taught sex education and my mother never talked to me about it either other than to say I should weight till I was married to have sex.

I thought that this summer would be just like last summer and that made me happy. On my first day of vacation I got up around 8:00, which is normal for me, and had breakfast with my mother before she left for work. My mother said that she had a sales meeting that night so she would be home late and she reminded that my father was on a business trip so Bobby and I would be on our own for dinner that evening, which meant that I would have to cook something for dinner.

Bobby got up around 9:00 and ate his breakfast then headed off to play baseball or whatever he and his friends do. By 11:00 Bobby was gone and I was comfortably seated in the porch swing with my latest book.

Around 1 o'clock it started to rain. I was sitting on the sofa in the living room reading when Bobby came in. Bobby didn't say a word to me as he walked past me to turn on the television. Bobby and I never talk much. We just kind of tolerate each other and speak only when necessary. Bobby came over and sat on the floor and leaned against the sofa. At the time I was sitting with my feet up on the coffee table. After a while I looked up from my book to see Bobby looking up my dress. I yelled "What are you doing?" Bobby just laughed at me and went up to his room.

Later that day I went upstairs to take a shower. While I was showering Bobby walked into the bathroom and then acted surprised as if he didn't know I was in there. I knew that he heard the shower running. He was just trying to bug me and it was working.

The next morning my mother told me that my father would be home that evening so she wanted me to make sure and get the laundry done before he came home. As soon as my mother left for work I went upstairs to get the dirty clothes from the upstairs bathroom and took them down to the laundry room. Bobby was just getting up as I took the laundry down. Next I went into my parents bathroom downstairs. I picked up the laundry hamper and took it to the laundry room. I dumped the contents on the floor to sort the clothes. The skirt my mother had worn to work the day before fell in a ball on the floor and when I picked it up a black bra and black panties fell out. When I picked up the panties I noticed that there was something white and crusty dried on the gusset. I was wondering what she could have gotten in her panties that would leave a mess like that when I noticed something on her skirt that looked very much the same. I figured she must have spilled something on her clothes as she was getting undressed last night. I set the bra and panties aside and started a load of whites. Bobby was eating his breakfast so I went upstairs to make the beds and take a shower.

When I was showered and dressed I went downstairs to do another load of laundry. When I went into the laundry room I noticed that my mother's black panties were missing. I looked all over the launder room for them. I sorted through all of the other laundry and looked behind and under the washer and dryer but I couldn't find them. I retraced my steps around the house to see if I had carried them out of the laundry room without realizing it and dropped them somewhere else. But I didn't find them.

Puzzled and confused I walked into Bobby's room to ask him if he had seen the missing panties. When I looked at Bobby I opened my mouth to say something but no sound came out. Bobby was naked and laying on the bed. With one hand he was holding my mother's panties up to his face and he had his other hand wrapped around his cock (I call it a cock here but when I was fourteen I didn't know what to call it. In those days I would have said it was his 'thing'). I stared for a few seconds and then I shouted "What are you doing?" and I walked over and grabbed the panties out of his hand.

Bobby started yelling at me to get out of his room and I yelled back "Wait till my mom finds out about this."

I took the panties down to the laundry room and put them in the washer then I went up to my room and closed and locked my door. At the moment I was a little afraid of what Bobby might do. I knew he wouldn't want me to tell my mother about what he had been doing. I knew that I couldn't tell her anyway. I could never bring myself to describe what I had seen to my mother. I had never seen a cock before. Well I had seen them on little boys when I was baby sitting but I had no idea that they got that big when the boys grew up... It must have been five or six inches long and as thick as a sausage. I wondered what he was doing to it and what was he doing with my mom's panties.

I found as I sat thinking about this event it was kind of funny and I was becoming more curious and less scared about what I had seen. It was at this point that I heard Bobby's door open and I heard him coming toward my room. I was beginning to get scared again.

Bobby knocked on my door and I asked what he wanted. He said he needed to talk to me and asked me to open my door. He didn't sound angry so I let him in. He sat down on the edge of my bed and said, "Please don't tell your mom."

I didn't say anything for a minute then I said, "I won't tell on one condition. You have to tell me what you were doing."

He said, "Come on you know what I was doing, I was masturbating."

I said, "Masturbating? What does that mean?"

He said, "Like jerking off? You don't know about that yet?"

I said, "I never heard of masturbating or jerking off. Just tell me what you were doing to your thing and what you were doing with my mom's panties."

Bobby looked embarrassed now but he said, "Okay. It's called jerking off when a guy gets a hard on and he rubs it up and down till he has a climax."

"Hard on?"

"That's when a guy gets sexually excited, his dick gets stiff and hard."

"Then what's a climax?"

"Boy you don't know anything do you? A climax is when after a guy rubs his dick he gets a real good feeling then semen comes out of it."

I didn't understand much of what he was saying but I felt some kind of an excitement growing as I listened to him. I asked him again "What were you doing with my mom's panties?"

Bobby said, "I wanted to smell her pussy scent in them." He finally said a word that I understood. Pussy. I knew what that was but I never thought that a guy would ever want to smell one.

I said, "Why would you want to smell that?"

"Because the smell gives me a hard on so that I can jerk off."

Although I didn't know what Bobby was talking about I understood him enough to know that I wanted to know more.

Bobby asked, "So your not going to tell your mom, right?"

"I won't if you let me watch you do it"

"Watch what."

"I want to see you do that jerking off thing."

"I can't do that with you watching."

"Why not? If you don't want me to tell my mom you have to show me."

Bobby said okay then started to open his pants. I said, "Not here. In your room."

We went over to Bobby's room and he closed and locked the door then he sat down on his bed and slide his pants down. I was surprised to see his cock was so much smaller now than it was when I saw it earlier. Bobby had a lot of hair around his cock and I noticed his sack for the first time. I ask him what it was. He said that's where his balls were. I wasn't sure if he was teasing me or if he meant it.

As I sat there looking at his cock I could feel a little tingle go up my spine. I felt kind of naughty but I liked the way I felt. I said, "Are you going to do it?'

Bobby said, "Give me a second." The he wrapped three of his fingers around his cock and began stroking it. Nothing happened for a couple of minutes. Bobby looked at me a couple of times then suddenly I saw his cock start to grow. I was amazed. Bobby began staring at me with a glazed look on his faced as he rapidly stroked himself. After about five minutes Bobby made a grunting sound and I saw his cock spasm. When it did this translucent liquid came out the end of his cock and ran down over his fingers. Bobby had his eyes closed now and he was breathing hard. From the look on his face I could tell he enjoyed himself. I found that I had enjoyed watching him very much so I asked him to do it again. He said, "I can't. I can only do this a couple of times a day otherwise it begins to hurt."

I said, "When can I watch you do it again?"

Bobby said, "Your not going to say anything to your mom?"

I said, "No, I'll never tell Mon. When can I watch you do that again?"

Bobby said, "You can come to my room tonight after your mom and dad go to bed."

I found that I was excited all the rest of that day looking forward to the prospect of watching Bobby jerking off. That evening instead of watching television with my mom and dad and Bobby I went up to my room and tried to read but all I could think of was the image of that semen, as Bobby called it, coming out the end of his cock.

Finally around 11 o'clock I heard the television go off and then I heard my parents bedroom door close. I waited for fifteen minutes then I slipped out of my room and over to Bobby's room. His door was unlocked and when I went in he whispered for me to lock the door. I did and went over and sat on the edge of his bed. He pushed his blankets down and I was surprised to see that not only had Bobby already removed his pants but he already had a hard on. I asked him why it was already hard. Bobby said, "It's been hard all evening. The thought of having you watch me tonight got me very excited."

This time it didn't take Bobby very long before he climaxed. I enjoyed the show but I had hoped it would last longer. Afterward neither of us said anything. I got up and went back to my room and tried to sleep. As I drifted off to sleep I was hoping that Bobby would let me watch him again sometime.

The next morning Bobby didn't say a word to me. He just got up, ate breakfast, and went off to play baseball. He came back home around 2 o'clock. I was sitting on the porch reading when he passed by without a word. I guessed we were back to just tolerating each other again. About twenty minutes later Bobby came back out on the porch and said he wanted to talk to me up in his room. I immediately got excited thinking I was going to get to watch him again so I followed him up to his room.

When we got to his room he told me to sit down, which I did on his bed, then he stood in front of me or rather he paced in front of me. Bobby sighed then started talking "I've been thinking about this since after, ah, you know, last night. I decided to tell you this and I hope you don't get angry. Remember the other day when it was raining and you were sitting on the sofa reading and I was sitting on the floor. Remember you looked at me and asked me what I was doing?"

I said, "Yes I remember."

"Remember that I just laughed and went upstairs? Do you know why?"

I said, "No, I don't know why. How would I know?"

"I went up to my room to jerk off. You see I had a hard on from looking up your dress. While you were sitting with your feet on the coffee table I had a perfect view all the way up to your panties."

I started to speak but Bobby stopped me and said, "Then remember later that day when I walked into the bathroom while you were in the shower. That was not an accident. I knew you were in the shower. I wanted to see you naked so I could jerk off while I thought about your naked body."

I said, "I don't understand. Why would you get a hard on from seeing my panties and why would you want to see me naked? And why would any of this make you want to jerk off?"

Bobby said, "I noticed this year that you are turning into a woman. Well actually my friends pointed it out to me. They told me that they thought you were sexy."

"They said I was sexy? Who said that?"

"Troy and Dan. Anyway after they pointed it out I could see it for myself. They kept saying 'Boy you're lucky. This summer you're going to get chances to see Jenn naked all the time.' Until then I had never thought about even trying to see you naked."

The idea that his friends thought I was sexy made me feel good even though I didn't know for sure what they meant. I asked, "Why are you telling me all this?"

Bobby said. "Well other than the quick peek in the shower the other day, and I didn't see much because the shower was all steamed up, I have never seen you naked. So I was thinking that if you enjoy watching me jerk off then maybe we could work out some kind of a deal."

The mention of watching Bobby jerk off got my attention. "What kind of deal?"

"Well I was thinking maybe you would take your shirt and bra off and let my see you boobs while I jerk off. That way we both get to see something. Do you think you could go along with that?"

I don't know why but the idea really appealed to me. I didn't want Bobby to know I liked the idea right away so I said, "You really think I am going to let you see my breasts? I don't know if that is such a good idea."

Bobby sat down on the bed next to me and looked at me and said, "Come on Jenn, please?"

I didn't say a word. I just got up and walked to the door. I could feel his disappointment. I enjoyed the effect I was having on him even if I didn't know why. When I got to the door instead of leaving his room I closed the door and locked it. Then I turned around to face Bobby and said, "You go first."

Bobby had his pants off in a flash. His cock was not yet hard but it was growing. I slowly unbuttoned my blouse. I don't know how I knew to tease him b moving slowly it just seemed to come to me naturally. I removed the blouse and set it on the bed then I unhooked my bra and let it slide down my arms. The effect was immediate. I could see Bobby's face get a little red and has cock looked even bigger and harder than it had been the night before. As Bobby began stroking himself I went and sat next to him on the bed.

Bobby never removed his eyes from my breasts the whole time he was jerking off. This time when he climaxed his semen actually shot out and landed on his leg.

We decided that we should never do this when either of our parents were at home so over the next couple of weeks we played our little game about seven times. I thought that Bobby would get bored looking at my boobs but he didn't. There was a period of about five days when I didn't go into Bobby's room at all. The key word there is period.

The next time we got back together I was sitting next to Bobby with my boobs exposed as usual and Bobby asked, "This time would you lift your skirt up so I can see your panties too?"

I did as he requested. I was a little embarrassed when I realized that I had on an old pair of panties that had pictures of animals on them. Bobby didn't say anything about my panties until after he was done. He just said, "Next time don't wear your baby panties."

The next day I put on a new pair of panties. When I showed them to Bobby he just stared at them for the longest. Then he said, "You are really sexy. Seeing you like this makes me so hot." The he began jerking off and very soon shot a load all over his sheet.

I found that exposing my self to Bobby this way was making me very excited but I had no idea what it meant I only knew that I liked the way I felt.

A couple of days later as I putting clean laundry away in my mother's room when I mistakenly opened my mothers lingerie drawer. Sitting on top were the black panties that had started this whole deal with Bobby. I decided to play a joke on Bobby so I borrowed the panties.

I went an took my shower and put the panties on, then waited for Bobby to come home. Bobby came in the house a couple of hours later. He washed up then came an asked me if I wanted to play, which was the term he use for what we did. I followed him up to his room and I waited till he removed his pants. Then as he watched me I slowly lifted my dress up until the black panties were exposed. Bobby almost went nuts. He yelled "Wow! You look so sexy. Oh my God, Wow!" When I took the dress completely off Bobby asked me to turn around slowly.

I was hoping to get a good reaction from him but I never expected anything like that. His reaction made something happen inside me that I couldn't explain but it sure felt good.

I just stood in front of Bobby with this tingling sensation that seemed to be radiating from my pussy and going all through my body and Bobby just sat there staring at me. Bobby just looked at me for about a minute then he started jerking off as he stared at me. This time when he climaxed some of his semen landed on my hand. I don't think Bobby noticed so I didn't say anything.