Chapter 3: Bobby’s & Sindee’s First Time

A Word to the Reader –

Please remember that this is just a silly little fantasy. I mean, what company would actually be in the business of making sex videos with performers as young as 14? Because, I mean, after all, that would be illegal – wouldn’t it...?

~ ~ ~ ~ ~

After half an hour, like she said, Janine found us and started talking about what she had in mind next.

“Bobby, Sindee, from what we’ve seen you do, and the chemistry between you, Ed and I have been thinking, and we think we’d like to do several videos of you two, together. I mean, as a couple.”

I never even thought of something like that before, but yeah, I like Helen, so ... sure. I looked at Helen and she didn’t say anything, but she had this look, like she liked that idea.

“So anyway, now that you’re ... warmed-up ... we thought we could shoot the very first scene today. How does that sound?”

Both of us said okay, so Janine went on. “We can use set 8 – the ‘high-school girl’s room.’ Sindee, it’s after school and you take your boyfriend Bobby up to your room like you’ve done lots of times before, but this time it’s different because you know that your parents won’t be home from work for several hours and you’ve decided that you want to have sex with Bobby and that today’s the day. And of course it’s the first time for both of you so you’ll need to act shy and uncertain – and inexperienced – but you figure it out and you end up fucking, and it’s hot, maybe even a little dirty if you can figure out a way to do it without ruining things – but it’s all romantic.

“Any questions? Got that?”

So Helen says “Bobby, why don’t you go down to set 8 – I just want to ask Janine one thing.” So I say okay and head down the hall but I can hear Helen and Janine talking, and Helen’s asking, “How about...?” and “Wasn’t Bobby supposed to...?” but I see Janine smile and put her hand on Helen’s arm, and I think she says to Helen, “Don’t worry, Dear – in case you can’t see it, that boy has a major crush on you – he’ll do anything you ask...”

So anyhow I get to set 8, and like Janine said, it’s decorated to look kinda like a teenage girl’s room. There’s a small desk with a bookshelf on it and a lot of stuffed animals and some knick-knacks, and it’s got some music posters on the wall, and there’s what looks like a school pennant. And a bed, of course, with a girly-looking spread and ruffles around the bottom and more animals on it.

When Helen got to the set she wasn’t wearing her dressing gown (or high heels) anymore. Instead she was dressed like I guess a normal teenage girl would if she was getting together with her boyfriend at her home after school – nice plain white T-shirt and jeans that’d been washed a bunch of times and white canvas tennis shoes without any socks.

Also, now she wasn’t wearing a bunny ears or cheetah ears headband – just her regular hair. It looked like it was freshly brushed ‘til it almost shined, and it looked really soft. Janine decided that what I was wearing – a Smashing Pumpkins T-shirt and my boarding shorts and black-and-white checked Vans – was the right look for the teenage “boyfriend.”

Janine seemed to know that this scene will be a big step for both of us, so she says, “I’ll give you two some time to get used to the idea, maybe talk some things over about what you’d like to do, how you’d like to do them, OK?”

So Janine walks back to talk with Carl the cameraman (except now they don’t call them “cameramen” any more – they’re “videographers”), and she and Carl sit down and make some notes, probably of things they want to be sure to get in the scene, and that’s when Helen takes my hand and leads me over and we sit down on the bed with the ruffled spread, and she starts talking, like there’s something she needs to explain to me.

“You know, Bobby, my birthday is April first, April Fools Day, so I’ve only been coming to the studio two months longer than you have. And the times I’ve been here they haven’t really had me do a lot of things. Mainly it’s been stuff like the things you and I did the first time...,” and it hit me again – that that “first time” seems like almost a lifetime ago, “ ... you know, like posing and arms around each other and kissing with boys and girls.”

Huh? The idea that Helen’s posed “like that” and maybe even kissed with girls really surprised me. Mainly because I didn’t know why anyone would want pictures of Helen kissing a girl. But she explained that girls can kiss girls, and also, that there’s other places besides on the lips that they can “kiss,” and she tells me about how girls can “kiss” each other between the legs. So of course I ask what’s so special about that, about girls kissing each other between the legs, and she explained that it’s not really “kissing” – “ it’s more like they use their tongues to lick each other between their legs...”

And it’s finally started to dawn on me. “You mean, like, licking their pussies??”

And Helen says yeah, licking their pussies... “ ... and also licking and sucking on their clitorises, and sometimes even putting their fingers inside each other...”

I heard of “clitorises” before, but I gotta admit, I wasn’t real sure what they are, or where they are or what they do. But from what I knew, I wasn’t sure why anyone would want to lick or suck on one. But I didn’t think that Helen wanted to talk about that right now so I stayed quiet.

And then she lowers her voice, like she’s going to share a secret or something. “Also, they aren’t always ‘girl’ girls. Sometimes, they’re older girls, and even some women.”

But before I could get too caught up in that, Helen puts her hand on my bicep and says, “So anyway, Bobby, what I’m trying to say is – even though I been here several months and seen lots of different things that the people do here – lots of things – well, what I’m trying to say is ... I haven’t done ... that you’re the first boy I’ll be with...,” and because I didn’t react to what she told me, she explained, “ ... the first boy I have sex with...”

Well, that got me to react. Holy shit! Her first time! I mean, with her being around here, and all the stuff she knew – knows – and her being so confident and all ... And yet us – her and me – that’ll be her very first time with a boy – fucking a boy! Holy shit!

The other thing was, this is the first time anyone’s actually come out and said that Helen and I are gonna have sex.

Then I thought, maybe she’ll be as nervous as I am – maybe even scared. But then I knew that if I was going to be nervous and scared, I’d rather be nervous and scared with Helen than anybody else.

Janine saw that Helen and I had finished talking so she came over to us and told us how they wanted us to begin.

“Okay, Sindee, like we talked about, you’re in high school, maybe the 10th grade, and you know that your parents won’t be home for hours and you have the house to yourselves and you and Bobby have been dying to have sex but never had the chance. So you two come home from school and you invite Bobby up to your room, and you talk a little about the situation, and first you make out but then your hands get under your clothes and then you gradually lose your clothing and then, well – I think you know enough to take it from there. If we need anything Carl and I’ll tell you. You two good with that?”

So Helen – “Sindee” – and I look at each other, and I guess we got it and we don’t have any questions, and to tell the truth, I think both of us were kinda anxious to get started, ‘cause I think this is something that we both want. Then Janine calls, “Ready – take your positions – rolling!”

Helen – I’m gonna call her Sindee now that we’re in the scene – Sindee and I stand behind a wall where the camera can’t see us and Sindee says, “Let’s go up to my room, Bobby – we can watch some YouTubes or TikToks or maybe listen to music – I got the new Taylor Swift release...” Taylor Swift? For chrissakes! I’m a guy!

We go around around the wall and into the “bedroom” and Sindee put’s her book and her Mexican tote sack on the desk and I put my backpack in a corner out of the way. And we’re supposed to be just talking, or maybe looking online for some videos, and we’re standing real close, and then Sindee turns to me and puts her arms around my neck and says, “Ya’ know, Bobby, we been going out seven months now, and I really like you – do you like me, Bobby?”

So I know what to say. “Heck yeah, Sindee – you know I like you...,” and then I thought I needed to say something more, “ ... a lot.”

Then she says, kind of shy and uncertain, “Bobby – do you think I’m pretty, Bobby...?”

I knew I should improvise here. “Hell, yeah – I think you’re the sexiest girl in the ninth grade!” I was proud of that little bit of improvisation.

So Helen-Sindee moves even closer and presses against me and says “Do you really think I’m sexy, Bobby?” And before I can answer she presses even closer and pulls my head down and kisses me, and it’s not just a quick kiss – she made her lips real soft and pressed them against me and moved them, and I think I even felt her tongue licking around the outside of my lips.

And because I’m such a dummy she has to take my hands and put one of them on her T-shirt right where her breast was, and for the first time I realize she’s not wearing a bra under her T-shirt and I was relieved that we wouldn’t have that to worry about that later. She put my other hand low down on her hip and moved a little, and that told me that I was supposed to move my hand around to her ass. So we stand and kiss like that, with her hands around my neck and my hands on her breast and her ass – and it feels really good, my hand squeezing her ass like that.

But then Sindee, in between kisses, says, “Bobby?” and I say yeah, and she says “Bobby, I’d like to see you with your shirt off. Would that be OK?”

So I nod and she steps back and she starts tugging on the bottom of my Smashing Pumpkins tee, and when she gets it up to my armpits she tugs a little and I raise my arms and she pulls forward a bit so I have to bend over and she slips my shirt up over my head and off my arms.

Helen-Sindee’s seen me without my shirt, a coupla times now. But she’s a good actress and she acts like it’s the very first time she’s seen me without my shirt, except for when we’re at the pool or the beach and you’re supposed to be like that. And she looks like, well, like a girl’s supposed to look the first time she sees her boyfriend half-naked.

And she starts out acting shy, ‘cept she’s not, and real soon she’s touching and then kissing Bobby’s chest. But this time it’s different for me, ‘cause the first times I didn’t know what was supposed to happen and was kinda nervous – even a little afraid. But this time I knew what was happening, and even more, I knew where things are going to go this time.

So Sindee runs her hands over my chest and then “can’t help herself” and has to kiss her boyfriend’s chest, but before long she goes “off script” and in a way that the camera can’t see she licks and sucks and bites and pinches my nipples, and it’s so hot because I know she not doing it for the camera but because she wants to do it – for me, and maybe for herself, too.

Her hands are still wandering around my chest she says, “Y’know, Bobby, it’s kind of unfair – I made you take off your shirt but I haven’t taken off mine.” And I stand there like the dummy I am and she has to say “Would you like to take my shirt off, Bobby?” and my dry throat croaks out a “Yes.” So Sindee takes a step back and grabs the bottom of her white pullover shirt, but then stops and looks at me and gives me this shy invitation, “Would you like to help, Bobby?”

And I realize, a girl is asking me to help take her shirt off. She’s asking to show her tits to me! My throat’s still too dry to talk, but my arms have the sense to reach out and take the hem of her shirt that she’s holding out for me and together we peel her shirt up and she guides it up and over her head and off of her outstretched arms...

And Sindee’s standing there in front of me, and her chest is completely naked. And she’s beautiful! She was so smooth and pretty, and her tits – her breasts – were small, about the size of scoops of ice cream and shaped like little cones, with little pale pink gumdrops on the tips They were perfect!

Sindee watched me looking at her – at her breasts – and I could tell she was really happy that I liked her, that I did think that she was pretty, that that was important to her. And that made me feel special, that she wanted me to like her breasts, to think that she’s pretty.

“Wanna touch them, Bobby?” I still stood there like a stone, ‘til Sindee had to say, “I want you to touch them, Bobby – as much as you want.” She had to take one of my hands that was hanging uselessly at my side and move it up to one breast, and then because I still didn’t know what to do she squeezed my hand a little, so it squeezed the beautiful soft flesh. Then she took my other hand and put it on her other breast, then let go – and then my hands seemed to know what to do.

And what they did was the things I’ve dreamed about all the nights when ... But this time they’re real tits, on a real girl, a girl who wants me to touch them. So I ran my fingers over them, but after a while her nipples start to go from being soft little gumdrops to being gumdrops that aren’t so soft, and they’re not little anymore. So I played – toyed – with her nipples, and I think I mighta got a little too “enthusiastic” and Sindee put her hands on mine to slow me down.

But then she did something else. She put one hand behind my head and pulled me toward her, and down, ‘til my head was right next to one of her breasts. She moved my hand away and looked at me, then down at her chest, and it was obvious – she wanted me to put my mouth on her – on one of her breasts!

I surprised myself by not resisting, just loosened my lips and put them on her nipple. Then I took the whole breast in my mouth, and I was real careful to be soft and gentle when I licked, and ‘specially when I sucked on her, and she held my head closer to her and kinda of shivered for a couple seconds, and then she made a sighing sound and then loosened how she was holding my head.

After she sighed she took my hand and pulled me and said, “Bobby, would you like to get on the bed?” and she leads me over and shoves all the stuffed animals over to one end and gently pushes me back onto the bed and then she lays down on top of me and we start kissing and her naked chest – her tits – are pressing against my bare chest.

Well, I react like normal – I get hard. And I think I should be embarrassed, but then Sindee squirms herself against the stiff bulge in my jeans and I remember that that’s what her and me are here for.

Then Sindee puts her head beside mine where the camera can’t see her and whispers “I like it when you get hard, Bobby,” so I guess it’s OK. Better than OK.

Then she gets into character again she starts rubbing the bulge in my jeans, this time for the camera. First she just rubs per hand over the cloth, but then she starts rubbing harder, and then she grabs it inside my jeans and squeezes, so it hurt, but it’s exciting at the same time.

And that’s when she says, “I want to see this, Bobby, I want to see your cock.” And the way she’s talking, it’s kinda like she teasing me. “Would that be OK, Bobby, if I see your cock. I want to see your cock, Bobby.” And then she breathes in my ear, but loud enough that the camera mic can pick it up, “There’s no telling what I’ll do if you let me see your cock, Bobby...,” and she starts playing with my belt, and she unbuckles it, and she does it as fast as I could. She’s already undone my button and zipper twice today and she has them open in no time and then she says “Lift,” and I know she means to lift my hips, and then she pulls my shorts down and pulls them completely off me.

So now I’m laying there on my back and my cock is swollen and making a huge – well, big – bulge inside my new stretch undershorts, and that’s where Sindee’s hand went. She starts feeling me through the stretch material. She squeezes my cock and rolls it in her hand, and then she starts sliding her hand up and down. She was jacking me off inside my shorts! Then I felt her other hand feeling around my balls. She didn’t do much with them, just held them in her hand, holding just tight enough for me to know.

She took her hand off my cock, but just long enough to slide it down inside my shorts and then started rubbing and sliding her hand up and down my cock. I think it felt especially good because of the shorts. First, I think the stretch material holds her hand closer to me. Second, a pretty girl has her hand in my underpants and she’s jacking me off! It was almost like I was picturing what her hand is doing, pictured it squeezing and rubbing my cock. In fact, I think that might have been just as exciting as what her hand was actually doing.

But Helen-Sindee seemed to know that we – meaning she – needs to move the scene along, so she worms her warm soft hand out of my undershorts, and when she did I had this odd feeling, almost like I’d lost something. But it didn’t stay that way for long because right away I felt her hook her fingers under the elastic waistband and for the second time today told me “Lift,” so I lifted my butt and she skimmed my shorts down and over my Vans, so yeah, I’m laying there on this girl’s bed with my shoes still on my feet and my hard-on sticking straight up from my naked body. Weird.

Sindee gives my shorts a toss and they end up right on the face of a blue stuffed teddy bear, and she points and giggles. But then she leans down and puts her mouth down on my sticking-up cock and takes it all the way, ‘til her nose bumps up against me, and all the time I’m thinking that for the shy virgin she’s supposed to be in this scene she’s really going after my cock.

But this time it wasn’t like the test shoots we did, where she was focused on making a “show” of sucking and jacking my cock for the camera. This time she was a horny teenage girl and she was going down on me, on her boyfriend. And she was goin’ at it pretty good – and it was blowing my mind. First was the feeling. Before, Helen-Sindee’s mouth felt warm and soft and wet on my cock, and it felt so good I just wanted to melt in it. But this time Sindee’s jamming her mouth all the way down my cock, and this time it feels hot.

And I’m starting to really get into the scene now. I’m stretched out naked on this bed and I see this blond head deep-throating my 14-year-old cock, and she’s holding onto my hips so she can pull me closer to her, and my cock is starting to feel ways it never has before. It’s like I want to cum, but at the same time I’m too hard and too excited to cum. And maybe that’s what Sindee’s supposed to be doing now – making me want to come, real bad – but not yet.

Than she lifts her head off my cock and says, “Bobby, don’t you want to touch anything?” but I’m too dense, or let’s face it, too inexperienced to have a clue what she means. But then she rolls over beside me and takes my hand and puts it at the top of the jeans she’s wearing and tries to slide my hand inside her jeans. Except they’re still fastened, so she works her hand under mine and undoes the button snap and zipper and pushes the jeans down a little, and I can see that she’s wearing panties, and they’re nylon but not sexy, just plain pale panties.

Then she puts my hand back on her tummy, just at the top of her panties, and it’s pretty obvious that now it’s my turn to slip my hands inside her underwear and touch her – where? I know I’m supposed to slide my hand inside her panties, the way she put her hand inside my undershorts, so I put the palm of my hand flat on her tummy – it’s so soft and so smooth, and there’s no fat and I can feel the muscle that’s under the soft skin – and I wiggle my fingers ‘til they’re under the thin elastic waist band, and now I’m half-way inside Sindee’s nylon underwear. I’ve got my hand in a girl’s pants!

And I just kinda freeze there, thinking “I have my hands in her pants,” and I think my cock actually jumps at the idea.

But “inside” isn’t enough for Sindee. She takes my wrist and presses it down, farther into her pants, ‘til I touch, you know, ‘til I feel the soft hair, and then I know that I’m touching her pussy. And Sindee knows that she needs to let me know, so she goes, “Mmmm, ” and that tells me that she likes it – that she likes my hand on her pussy – and that maybe I should do more.

Right now I’m hung up on the fact that I’m feeling a girl’s pussy hair. I move my fingers around, just feeling the soft fluff, kind of exploring and wondering what color her pussy hair is. Is it the same color as her hair, or darker – or maybe even blonder. And then I notice that the feel of her hair on my fingertips – and knowing where that hair is – is getting me hard again.

But Sindee’s getting tired of waiting for me so she takes my wrist and pushes my hand farther down, ‘til my fingers reach a spot where the hair parts – and I’m touching the slit between her legs. And I’m paralyzed, and then Sindee, with her hand outside her panties, presses down on my finger – and I feel it. The wetness. My finger’s in Sindee’s pussy. My finger is in a girl’s pussy! I never thought this’d happen, at least not for a long time.

So now my finger’s in Sindee’s wet pussy and she’s pushing on it through her panties to make it go deeper. Then she spreads her legs and she lifts – kind of tilts – her hips up, and she’s forcing my hand and finger farther down and farther into her and moving it back and forth inside her – inside her wet, slick pussy. But I don’t move – I’m still afraid to do anything – afraid I’ll do something “wrong.”

Sindee finally has to tell me, “Go ahead, Bobby, it’s alright. Move your finger in me, do whatever you want – it’ll be OK.” But then she says in a half-whisper, like part of it is for the sound guy, but part of it is just for me, “Whatever you do, I’ll like it.”

That makes me feel more confident, so I start by using just one fingertip to move around in Sindee. This is my first time touching a pussy, and I feel around, almost like I’m “exploring.” I curl my finger and put the tip inside her, inside her hole, and move it around, and when I do this she makes this sighing sound and moves a little. Then I take out my finger and slide it up and down the slit, just to feel it, and I decide that touching a girl’s slick pussy juice is about the most mind-blowing thing in the world. This sounds weird, but the feeling of that warm slick juice on my fingertips might even be more exciting than when I actually came in Helen’s mouth earlier today. Sounds crazy, but that’s what I was thinking.

Then Sindee says, “Bobby, do you think that we...” (we!) “can do it better with my jeans off,” and without waiting for me to think about such a complicated question she lifts her hips and pushes her jeans and panties down to her feet, then kicks off her canvas tennis shoes, then kicks her jeans and panties the rest of the way off ‘til they’re in a pile at the foot of the bed. Then she says, “There, Bobby – nothing’s in the way now...”

So Sindee’s laying there completely naked right next to me, and I’m totally naked (except for my Vans), and what Sindee’s just told me is, basically, “Anything goes.” And I’m still such an idiot that she finally has to take my hand and put it between her spread legs and put my finger inside her slit again.

But now that I know what’s going on, this time I remember to move my finger, and I’m starting to get that feeling back, that feeling of sliding my fingers up and down through that warm, oily flesh. And the feeling’s amazing – and so nasty! And that’s when I think of the words: cunt lips. I’m sliding my bare fingers through Sindee’s hot, oily cunt lips! It’s so dirty that I wonder if it’s really OK for me to be doing this. But then I remember what Sindee said: “Nothing’s in the way now...” So anything’s alright.

I’m really getting into it now, and I get braver, sliding my finger farther up and down through her slit, and my finger’s up near the top of her slit when I feel this bump. It was kind of like a pimple, but real slick, but then Sindee arched her hips and made a noise like “Ahhhh...” and pressed my hand to her there and wouldn’t let me move my finger away, so I figured that that must be some kind of special spot for girls, or at least for Sindee.

But because I’m still an idiot Sindee has to coach me. “Put your finger – your fingers – inside me, Bobby. I want you to put your fingers inside me, and that’ll get me ready for...” but she didn’t finish. So I slid my fingers inside her pussy – into her cunt – and started moving ‘em around inside her ... there. And that’s when she started squirming around under my hand like she was trying to get away from my fingers – but also, like she was trying to get them more places inside her.

When I got to know more about Sindee in the months that followed I learned that it was both those things.

And I must’ve been getting better at it ‘cause Sindee grabbed my hand, my wrist, to keep me from taking it away, and she kept squirming when I got braver about moving my fingers around inside her. I kept moving my fingers around, trying to touch more places, but also to get deeper inside her. Then I got the idea to use my fingers like a cock, so I held my first and middle fingers together and started sliding them in and out of Sindee’s ... cunt, moving them like I pictured a cock would. I was fucking Sindee with my fingers!

And it seemed like she was liking it, having me fuck her ... cunt ... with my fingers, ‘cause now she was holding onto my wrist so I couldn’t move and started humping her hips, her pussy, up against my hand. It was like I was fucking her with my fingers and like she was fucking them back.

But then it was like she was trying to calm down – to slow things down. She stopped humping back at my fingers and lowered her hips onto the bed and stopped pressing my hand into her and took it and moved it away, out of her. But then she said, “That was wonderful, Bobby. Did you like doing that, Bobby? Because it – you – made me feel really good?”

When Sindee said that it made me feel ... proud! It was like I – Bobby the Idiot – was able to make a good-looking girl “feel good.” Like I was some kind of great lover or something! But then she kisses me on my chin and says, real low, “Bobby?” and I say yeah and she says “Bobby? You know how good it felt, when I ... when I put my mouth on you ... put your cock in my mouth, and ... you know ... used my mouth on you... ‘til you came?”

Yeah, I remembered! I can still almost feel her soft mouth around my hard-on.

“Well...,” she says, in a way that feels like she’s trying to coax me to do something, “now you can make me feel good like that, too.”

Huh? Me make her feel good like that?? She doesn’t have a cock!

But Sindee knew me enough now to know I didn’t have a clue what she was talking about.

“I know I don’t have ... what you have down there, Bobby ... but I have something else.”

I still didn’t have a clue what she was getting at.

“You know what I mean, Bobby. After all, your fingers have been touching it for the last ten minutes.”

No reaction.

“You know. It’s where you’ve been touching me. You know, my ... pussy...”

Huh? She wants me to suck on her pussy? How would I even do that??

“How would I even do that?”

She smiled, like at least she finally got through to me.

“You’d just do it kinda like I did with you – I open my legs for you and you get between them and then you ... kiss ... my pussy ... and stuff...”

Me? Kiss her pussy? That’s gross!

But it was like she already knew I was going to say that. “I know what you’re thinking, Bobby, and it’s not like that at all. Here, I’ll show you,” and she took my hand, the one I used to rub her pussy, and she lifted it so it was right next to my lips.

And the first thing I notice is the smell. It was ... it wasn’t like anything I ever smelled before. Or like anything I ever imagined. It was ... well, it wasn’t gross. It didn’t smell like pee, and it didn’t smell like sweat or old underwear. It smelled like ... warm human. Actually, warm girl. And like I said, it wasn’t bad, but at the same time I wouldn’t call it good, neither. The closest I can come is like cheese. I don’t mean it smelled like cheese. But you know how some cheeses have this funky smell but they end up tasting real good? Well, that’s the reaction I was having to the smell on my fingers.

Then Sindee tells me to relax my lips, then she presses one finger against my lips and says “Taste it, Bobby,” and somehow she knows just how to ask me so I want to do what she says. So I loosen my lips a little and my tongue touches the finger she holding to me. My finger’s dry by now but I can get some of the taste, and it’s weird. It’s kinda sharp, a little bit like pee would taste, but without the pee smell, but there also that warm funk I told you about. But then it’s gone real quick.

Then Sindee runs her own finger through her pussy a couple of times and holds it up to me – up to my lips – and says, “It tastes even better when it’s fresh.” So of course I don’t get what she means, but she held her fingers against my lips and I can feel that they’re wet this time and she tells me, “Taste.”