Where it happened: boyfriend's apartment
Langauge: english
Sex: Female
Rating: 5
Category: Straight
Hi, My name’s Cindi. I wrote earlier on this website about Doing It with my boyfriend in the back seat of his car at Lovers Lane, when there was another couple in the car with us. Now he wants me to write about how I first started masturbating. He already knows all about it. He’s standing right behind me now, reading over my shoulder as I write this.
When I was younger, I was a Tomboy, and my current BF was dating my big sister. One day I climbed in the window of the bedroom we shared when she went downstairs to talk to him on the phone. She had been writing in her diary, which she always kept locked up, but she left it there on the desk in our room when she rushed off to answer the phone. Being curious, I started reading to find out about her big hairy secrets. I got an eyeful! I found out that she was Going All The Way with him when they were out on dates. She really liked It. I sneaked down to the kitchen to listen in on their conversation. At first it was all about school and teachers and stuff like that, but after a while he asked her if she could go out that night. Our Mom had a date, so my big sister had to stay home and watch me. He was disappointed, and then he suggested that he could come over. My sister told him Mom’s Rule: No Boys In The House When Mom’s Not Home. He sweet talked her until she finally gave in. She finally told him he could, but he would have to wait until I was asleep, and be very quiet. After that, he asked her what she was wearing, and she said her faded jeans and a T-shirt. Then he asked what she had on underneath, and she told him! She told him in a shy voice that she was wearing her blue bra and her light blue panties. He told her he wanted her to “think” about what was going to happen when he came over. She asked why, and he said it was because he wanted her to get really wet. He said he loved how wet she got. She said, “I’m probably getting wet right now, just talking about it like this!”
They talked some more about arranging their secret meeting, but there wasn’t any more sex talk, so I hung up the phone quietly. I watched my big sister the rest of the day, wondering what they meant by her “getting wet”, and how it felt to know that in a few hours her boyfriend was going to come over and Do It with her for sure. She caught me staring, and said “WHAT??!” After that, I pretended to ignore her, but I could tell she was getting pretty excited. She kept rubbing her bare arms unconciously. Our Mom left for her date, and Sis got more agitated. Finally my bedtime came, and she reminded me of it “on the dot”. I knew what was going to happen, so I didn’t put up a fuss to try to stay up past my bedtime. I went right upstairs and took off my T-shirt and bra. My breasts were new, small and pointy. I put my T-shirt back on, and took off my jeans. I left my panties on. That’s how I slept back then – in a T-shirt and panties.
I stayed awake and looked out my bedroom window, waiting for him to come over. I saw his car arrive and park a block away. He sneaked through the dark back yard to the back door.
I waited for a while, and then stealthily opened the bedroom door and went sneaking down the hall to the top of the stairs. My big sister and her BF were on the couch, making out. I sat down on the rug and watched them.
They made out for while, french kissing and stuff, and finally he started feeling her up. She let him feel her breasts through her T-shirt and bra, but when he tried to take her T-shirt off, she stopped him. I could see that her nipples were erect under her clothes, and I wondered what it felt like to let a boy do those things, so I started imitating what I was seeing on my own body. I cupped my own small breasts through my T-shirt. My nipples got hard, and I felt the thrills that they sent down my spine and belly, and into my pussy.
They went back to making out, and he felt her breasts some more through her clothes, but when he tried to reach up under her T-shirt, she wouldn’t let him. So he dropped one hand to her knee, and started caressing her leg instead. He touched both of her thighs, and his hand climbed slowly up them as he continued to french her and feel her breasts with his other hand. Her legs drifted slowly apart as his hand climbed her thighs. After several minutes, his hand was almost at her crotch, and her legs were spread wide, and that’s when I noticed a darker blue spot on her jeans, about the size of a quarter, right where the seams met in her crotch. It looked like she had gone pee a little in her pants. Suddenly I knew what they had meant by her “getting wet”. I realized that her pussy was wet – so wet that her juice had soaked through her panties to darken her jeans. I wondered if “Thinking” about them Doing It and caressing my breasts the way he was touching her would make me wet, too. I pushed my hand down inside my panties to touch my pussy, and discovered that I WAS really wet and slippery down there.
My sister stopped him again, and stood up. I ducked behind the wall so they wouldn’t see me and waited. When I dared to look again, they were going through the door to the basement. They shut the door after them.
I waited for quite a while for them to get busy again, and then I tiptoed to the basement door. I opened it a crack and listened. After a minute, I heard my big sister moan, and the end of a kiss. I sneaked slowly down the stairs, being careful not to step on any boards that would creak, and when I reached the bottom, I peeked around the corner into the Rec Room, where they’d left a light on. The first thing I saw was my sister’s T-shirt, lying discarded on the floor. I leaned in a little further, and saw her bra, also on the floor. I backed into the laundry room, where it was dark, and (I hoped) I couldn’t be seen. Then I moved forward so I could watch.
My sister was laying on her back on the rug, naked to the waist. Her BF lay next to her. Her nipples were hard, and he was toying with one, while he sucked on the other one. Her jeans were unzipped, and his other hand was down the front of her pants. It was inside her panties: I could see the lacy blue waistband stretched over the back of his wrist. She had her legs spread wide for him, and the bulge that his hand made in her pants went all the way down to the center of her crotch, where her wet spot was. As I watched, he began to move his hand up and down in her pants – up and down, up and down. His mouth left her erect nipple and returned to her mouth for another long, hot french kiss. Finally she broke their kiss, and started to pant and moan softly. Her hips began rocking on the floor, as she pushed her pussy up into each of his downward caresses. After several minutes of this, she started to get frantic. Her hips rocked faster, and she caught her lower lip between her teeth, while her voice rose and took on a kind of whimpering, begging sound. They continued this way for a few more minutes, while the pitch of her voice went up and up, and her hips rocked faster. Then she said in a stressed voice, “I’m gonna… I’m gonna… I’m gonna cum!”
She arched her hips up high and convulsed several times, uttering deep moans of completion.
Whe she was done, her BF pulled his hand up out of her pants. His first two fingers glistened with her moisture. He reached for the waist of her jeans with both hands. She arched her butt off the rug, and he pulled her jeans and panties down. When she was naked, he stood up and skinned his T-shirt off. I could see a bulge that stretched his fly. I knew it was his erection, but it looked too big! He unzipped his jeans and took them off, and his erection sprang up, even bigger that I had imagined it to be. Just when I was thinking that it would have to hurt to have that put inside, he knelt between her widespread legs and lay down on top of her. He reached between their bodies, and I couldn’t quite see what he was doing for a minute, but then he pushed his hips forward, and she gave out a little gasp. He rocked his hips gently, in exactly the same way she had been when he was Doing Her in her pants. After a moment, his hand came back out from between their bodies, and his hips rocked deeper. She moaned again, louder. His hips began rocking big, and picked up speed.
He was fucking her! A white hot thrill went through me as I told myself that inside my head. I sank to my knees on the cold laundry room floor, and pushed my hand past the waistband of my panties and down inside. I got my finger wet, and began to explore myself there. It only took a few seconds for me to find the erect little nubbin that was the center of incredibly good sensations. I masturbated while I watched them Do It, and I pretended and imagined that I was the naked girl lying there on the rug with my legs spread wide, getting fucked by a boy.
This went on for several minutes, while my sister’s voice climbed the scale again and their movements got faster and jerkier. I knew why she was making those sounds – the feelings I was giving myself were unbearably good, and they just kept getting better and better. It was hard for me not to moan, too. Finally my sister arched up again, and began to convulse and cry out as she came, and I came too. I know I moaned softly when it happened – I couldn’t help it. I was glad that my sister’s cries were loud enough to cover my moans, so they didn’t hear me and catch me spying on them and masturbating in my panties.
They did more things that night. He pulled his erection out of her after she came, and it was glistening with her juices. He laid down next to her and caressed her slowly while she caught her breath, and then he began slowly caressing her breasts again. They made out while he felt her up, and after a while one of his hands went to her pussy, and soon her hips were rocking again while he kissed and nibbled his way down her neck and Did her pussy with his fingers. Hew kissed his way lower and lower on her body, past her breasts and newly erect nipples, down into her pubic hair. Then, he spread he pussy lips with his fingers, and his tongue darted onto the nubbin at the top of her pussy slit, and she took a deep breath. His tongue was like a hummingbird’s wing on her most sensitive place. My heart almost stopped – OMG what must it feel like to have a boy do THAT !!! I started masturbating my own clit again as I watched.
He licked her there until she came again, and then he fucked her from behind. There is certainly nothing left to a boy’s imagination about a girl’s body when she gets into position for that! I could see everything – her ripe wet pussy lips, her opening and her taint and the little pink pucker of her anus. Her boyfriend moved up behind her on his knees and guided the tip of his erection to her pussy, just below her anus. I got to see everything that time. He fucked forward gently and entered her, then I saw his entire erection disappear into her. He held still while she gasped, and then he started fucking her again. I could tell by her cries that her pleasure was even more intense and desperate than before, and she came right away, and then again in just a few minutes, and then again when he reached a hand around her hip and stroked her clit while he fucked. After that he started fucking her really hard and fast, and his face turned red, and when she convulsed again he did too. I knew he was pumping his semen into her pussy.
I watched the whole thing, and masturbated all that time, but I kept slowing down my strokes when I got close to cumming again, because I didn’t want to make any more noise and maybe get caught. When they were done, I went quickly back up the stairs to the bedroom, and got under the covers of my bed. I replayed everything I had just seen in my mind like a movie, and I masturbated in my bed and came two more times.
I masturbated in my bed almost every night that, and when my big sister went away to college, I started masturbating in my room after school, too. I usually masturbate in bed when I wake up on Saturday and Sunday mornings, because I don’t have to jump right up and run around getting ready for school.
After I got my first boyfriend, and gave in to him and let him fuck me in the back seat at Lovers Lane, I stopped needing to masturbate on Friday and Saturday nights, because of course he fucked me on dates. When we broke up, I went back to masturbating those nights, too.
Now I have my second boyfriend, who used to date my big sister. I went right up to him at a party we both went to, and asked him to take me home. He looked so sad without my sister! We had a long talk about losing our Loves in the car on the way, and when he dropped me off, I grabbed him and kissed him on the lips. Boy, was he surprised. I ran up to my room and masturbated while I thought about how daring I had just been, and what might have happened. I hoped he would call me. It took a while, but he finally did call and ask me out. On our first date, we had a lot of fun. When he took me home, he kissed me goodnight, and I tried to show with my passionate response that I was ready and eager for more, but he just said good night. I went up to my room and undressed. My pussy was wet, and I had made my panties wet just being in the car with him. I masturbated in bed, while I fantasized that we had gone to Lovers Lane to Do It after our date. I made myself cum several times.
On our next date, I dressed up a little, and tried to be sexy for him. I wore a blouse that buttons down the front, and my bra that hooks in front between the cups. I wanted it to be easy for him to feel me up and undress my boobs, if he wanted to. I wore a short skirt with nothing underneath but a pair of bikini panties. I wanted my bare legs to invite his caress, and for him to know that very little stood in the way of his hands going up my skirt to my panties.
After our date, we made out in the car for a while in front of the house. When he made to open the door, I reached across and stopped him, and whispered, “take me to Lovers Lane.”
When we got there and parked, I opened my door right away and got into the back seat. He got out much more slowly – he seemed to be in a kind of unbelieving daze. We made out for a while longer in the back seat, and then he started feeling me up. I didn’t stop him, and he slowly touched me and caressed me and undressed me. He made me cum in my panties with his fingers. After that, he pulled my panties down and made me cum again with his tongue in my pussy. (It was incredibly way much better than I imagined.) Then he fucked me. I knew that his erection was bigger than my first boyfriend’s from when I watched him fuck my sister, but I wasn’t prepared for how much it stretched me when he rocked it all the way into me. I came again right away. I only came two more times after that before he did – he was really excited. He told me later that he had been completely bewildered by my eagerness to Do It with him. At first I just laughed and said I knew what was expected of me in the back seat at Lovers Lane. He wasn’t satisfied with that answer (he’s too smart!), and he probed until he found out the truth about my obsession with him.
My boyfriend says that complete honesty with each other is the only basis for a relationship, so I’ve answered all his questions about my body and my previous boyfriend and my sex life before him and my masturbation habits. When we can’t be together, he calls me up on the phone, and after we talk for a while, he lowers his voice and tells me what he’d be doing if we were alone. He describes how he would kiss me and caress me and undress me and make me cum with his fingers and his tongue and his cock. The first time he did that, I went right to bed and masturbated as soon as we hung up. The next time, I took the phone to bed with me so I could masturbate while he was talking. He caught me! Somehow he could tell that I was playing with myself, and he stopped and said, “Cindi, you’re masturbating right nowe, aren’t you?” I didn’t say anything, and after a pause, he whispered ever so gently, “aren’t you?”
Honesty.
“Yes”, I confessed in a small voice, while I felt myself blush hard. So then he wanted me to tell him exactly what I was doing as I masturbated, but I was too embarrassed to do that. So then he asked about my first time masturbating, and I told him all of what I just told you. So now he knows that I watched him fuck my big sister when I was 14, and that I masturbated while I watched them Do It. He knows that I masturbated after that over and over and over again, night after night, while I thought about him fucking me. (He knows I masturbated this morning in bed before I got up and came over to his apartment!) When I confessed all of this to my BF, it made me really hot to have to tell him these things, and I ended up masturbating again while I was talking. So then I told him everything he wanted to know when he first caught me. I described exactly how I was masturbating to him while I did it – how I was on my back, naked in bed with my legs spread wide. How I was playing with my erect clit, rolling it between the first two fingers of my right hand. I told him each time I dipped my fingers below to keep them wet and slippery. I rocked my hips on my bed, just like I do when he fucks me, and I told him that, and let him hear the rythmic squeaking of my bedsprings. I told how good it was, and how hot it made me to know that he was listening to me masturbate – and how I was going to cum. Then I did cum, real big, and I let him hear the noises that I made as I came over the phone.
The next day I went over to his apartment, and what do you suppose he wanted? He wanted to WATCH me masturbate, and I did that for him, too. I took off all my clothes and laid down on his bed and masturbated in front of him while he watched. He fucked me after I made myself cum.
I really want to masturbate right now while I write this, but my boyfriend says I don’t get to just yet. He says first I have to tell you what’s going to happen next.
He’s been reading this over my shoulder the whole time I’ve been writing it, and he’s been feeling me up. My blouse is undone, my bra is unhooked, my nipples are erect. My panties are wet. My jeans are unzipped. I really need to pee.
As soon as I finish writing the things he says will happen next, I have to stand up so my boyfriend can take my jeans down, and see and feel how wet I’ve made my panties. After he feels and sees as much as he wants to, I have to read everything I’ve just written here out loud to him. I get to masturbate in front of him while I read, but only on the outside of my panties, and I’m not allowed to make myself cum. Aftewr I finish reading, he says he’ll push his hand down inside my panties and play with my pussy until I cum in my panties. He says you should imagine me standing here, a petite redhead with freckles, small breasts, and narrow hips – panting and moaning as he Does me in my panties. He says that when I’m close to cumming, I’ll grip his arm for balance and go up on my toes, humping the hand between my legs frantically. Then I’ll cry out as I cum, and probably wet my pants, too. After that, he’s going to pull my panties down and fuck me on the floor.
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