Chapter 7: Backdoor to Romance

“Bobby, I’m going to ask my mom and dad to invite you over tonight.”

It was kind of like the parent version of a booty call, basically, “Mom, Dad, invite Bobby over tonight – we want to have sex.”

Fortunately, and like before, Jim and Elaine were cool about it. First, they already know that their daughter is having sex – duhhh – so they’re not concerned about that. And I think they feel better if it happens at home, under their roof (when she’s not at the studios, anyway).

And I think they feel good that it’s me. They know that I truly like Helen and that I’d never hurt her.

And that’s the way it was in the mall parking lot when they came to pick up Helen – and me. Unlike other times when they’ve given me a ride, we didn’t have a lot of conversation. It was like everyone knew that there was some “agenda” for tonight.

We had dinner, but it wasn’t special like the first couple times they invited me for dinner. I mean, it tasted good but I think it might have been leftovers from earlier in the week, probably like what I’d be having if I ate at home tonight.

So Helen and I stayed polite and talked with her folks, but I think we were both kind of fidgety, thinking about why we were here and what we really wanted to be doing. And I think her folks noticed it and let dinner wrap up quickly.

And Jim – I don’t know how he manages to be so nice – when we’re all getting ready to sit out in the living room, says, “Maybe you kids would like some time by yourselves...”

Helen went over and kissed his cheek and said, “Thanks, Dad” and turned and went up the stairs to her room with me following her.

As soon as we’re in her room Helen closed the door – all the way – and put her arms around my neck and kissed me and said, “We’ve been waiting for this, haven’t we, Bobby?”

Helen always seems to know what to say to make things feel special.

“And we don’t have to hurry – my parents will give us as much time as we need.”

As much time as we need? In case it takes us several tries to get it right?

Helen was still pressed up against me with her arms around my neck and she said, “Bobby, I been thinking about this for so long, almost...,” and she stopped, like she was embarrassed to say something, but then went along and said, “ ... almost from the very first time...”

Did she just tell me that she’s been thinking about us having anal sex since the very first time that ... that we did something?

“And when I saw you ... doing ... it with Ryan in that scene you did with Eve, I know it was bad of me, but every time you pushed into Ryan I was imagining it was me. It was like I could almost feel it inside me every time your cock went into Ryan’s ... into Ryan’s bum.

“But I won’t have to imagine it any more, not after tonight – will I, Bobby?”

I was knocked out. Is there any sweeter way to tell someone that you’ve wanted them to fuck you in the ass?

“I know what ya’ mean. I mean, I been thinking about this since the first ... since we did it in that first scene in the high school bedroom. But I never really thought it would happen. I wanted to ... to ask you, or maybe talk about it with you, but didn’t know how to ... I wasn’t sure how you ... I was afraid you’d be...”

She kissed me again. “But we don’t have to be afraid anymore, do we, Bobby?” and she kissed me again.

“But give me a few minutes...” and she kissed me one more time and went into the bathroom.

So I’m left standing here in Helen’s room and I’m wondering what I should be doing right now. I mean, what’s the proper “etiquette” for when you’re waiting to fuck a girl in the ass for the first time?

I decide to unbutton my shirt a few buttons and take off my belt and my shoes and socks, but I thought that undressing any more might be too much and that I should wait for clues from Helen.

In a couple of minutes the door opens and she comes back into the room and closes the door again. She’d gotten out of the jeans and sweater that she wore at the studio today and she’s wearing a simple man’s white dress shirt that she buttoned a couple buttons on. She’d brushed her hair and it was real shiny in the light from her bedside lamp.

And looking at her like that, for just a minute I forgot about what we were going to do tonight.

“I wanted to be ‘specially clean for us tonight.” And another kiss, this time on the lips, very soft.

She reached up and unbuttoned the last button of my polo and told me to “Lift” and pulled my shirt up over my head and off my arms, and that left me standing there shirtless. And just like she did that very first day we were together at the studio, she put one hand on my chest and she kissed it. And it’s weird. This little thing that’s almost not sexual at all is maybe the most... personal ... thing that’s ever happened to me.

She slid down and kneeled in front of me and undid the button on my jeans and slid the zipper down and grabbed the waist and pulled my jeans down to the floor. Then she hooked her fingers under the waistband of my underpants – since that embarrassing time at the first shoot I’ve started wearing the tight stretchy kind – and peeled them down and let them fall onto my piled-up jeans.

“Step.”

I stepped out of my jeans and briefs and I’m standing there completely naked in front of Helen in her man’s shirt. I undid the two buttons on her shirt and eased it back off her shoulders and she stood there and waited, and I know that I should put my arms around her and hold her and we just stood that way for a while, and I really liked that. Also, it helped both of us put off the new thing we’re going to do tonight.

Then I knew it was time for me to do something too. I let go of Helen so I could take the bedspread and blanket off the bed but I didn’t know what to do after that.

That’s when Helen said, “Bobby, I want us to be able to see each other when we do it.”

She sat down on the bed and stretched out and spread her legs, and then she reached out her arms to me and I let her take my hands and she guides me onto the bed and in between her legs. And the way she did it, I knew that she wants me to eat her, and I don’t mind, ‘cause to tell you the truth, I’m still kind of nervous. Besides, I like laying between Helen’s legs. It’s warm and soft there and it smells like pretty girl.

The first thing I feel is her pussy hair, and it’s blond and so soft and I could just run my face back and forth through it for hours but Helen’s going to want more. I stuck my tongue out and she spreads her legs a little wider and my tongue touches the delicate little inside pussy lips, and each time my tongue touches her there she sighs, just a little.

I ran my tongue up and down through those soft little flaps, tasting Helen’s ... tasting Helen. She smells and tastes like a mixture of talcum powder plus a little bit of pee and pussy juice. A lot of pussy juice – she was really wet!

She put her hands on my head and I put my lips around her clit and ran my tongue across the stiff slick little bump of flesh, then around it, and then across it again, and she’s rolling her hips in sync with my tongue, and all the time she’s making these sweet little noises and I thought she was almost ready to cum. But instead she reached her hands under my shoulders and guides me up her body, and we’ve done this enough for me to know that now is the time for me to slide my cock inside her.

Helen and I’ve gotten real good at this. She slipped her arm between us and took the tip of my cock and put it against her pussy and then used her hands to give a little shove on my butt, and I’m inside her and I’m feeling that slick warm feeling – a feeling that six months ago I wouldn’t have thought I’d ever have, or at least not for a lot of years. But now there’s this really pretty girl and she’s letting me feel this feeling and I can’t figure out how I ever got so lucky.

Now the head of my cock is just inside her pussy and the warm, soft, wet pussy flesh is all around the head of my cock, and she can feel my cock inside of her, and we just stop like that so we both can enjoy how good this feels.

Then she nudges my butt again with her fingers and I know I should start moving, and now I’m fucking Helen’s cunt, and by now we know each other’s rhythm and we can just rock away and enjoy the feeling – her feeling me – feeling my swelled cock filling the empty space inside her cunt and me feeling my cock sliding in and out through the warm, slippery flesh and the gentle squeeze of her cunt muscles.

Now her hands are on my arms – on my biceps – and she’s holding me up so I’m not laying on her. I know she does this so we can look at each other – so we can watch the other person fucking us.

And it’s real good, and then Helen says, “Bobby?” and I say “Yeah,” and she says, “Bobby, do you think it’s time? I’m ready ... if you are...,” and I think for a sec and I say, “I’m ready if you are,” and I lean down and kiss her nose...

And then I realize that I don’t have a clue about how we do this, or what to do next. Fortunately, Helen – no surprise – has been thinking about it – a lot, it turns out.

“I want us to do it this first time like this, with us looking at each other...,” but then she adds, like a question, “If that’s alright with you...?”

Of course it’s alright with me. Standing up in a hammock would be alright with me just so long as it’s with Helen.

Then she says, “I think if you pull out, and then I lift my legs backward, so that ... so that my bum is pointed up higher ... to where ... you know ... to where it’s easier to get to...”

So I pull out of her pussy and she pulls her legs back and that tilts her hips up ‘til...

And then I thought of something – something important – something real important.

“Don’t we need something ... you know ... something...”

She smiled, like she was glad I thought to ask about it.

“When I was in the bathroom I put on some of this cream that Mom gave me to use, and also some – lots – inside me.”

And for some bizarre reason the first thing I think of is, “Your Mom gave you this cream...?”

So she explains, almost like she was embarrassed about it, “Well, she didn’t actually give it to me – more like she set it out on the bathroom counter, like where I’d be sure to see it...” But then she added, “But maybe it’d be a good idea to put something on you ... you know ... just to be sure... ”

And, yeah, I think that’d be a good idea – “just to be sure.” So Helen reaches over and gets a squeeze bottle from her bedside table and says “Scoot up closer.” So I kneel over her, and my cock is sticking out in front, and she takes the squeeze bottle and points it over my cock and squeezes a big glob of a jelly-like stuff onto the tip of my cock and starts spreading it around – first the head of my cock and then another squirt for the length – and then another squirt, and she spends a lot of time spreading this around the head...

And the way she’s spreading it, it feels really good, and I know she’s doing this so it’ll be easier for me to ... for us to ... tonight. But I’m also thinking that I wouldn’t mind having this spreading the lube jelly be the main event some time.

But she finally stops spreading it around and snaps the spout on the plastic squeeze bottle shut and puts it back on the table and then she looks at me, and then I remember something else: it’s not how deep – it’s how loose.

So I reach over to the table and get the squeeze bottle of lube and squirt a bunch onto the tips of two fingers, and being real careful not to let any drop on the sheets I tell Helen, “Pull your legs back again.” She does, and then’s when I tilt my gloppy fingers toward her pink little asshole and start to work my fingers around.

And for some reason, I remembered, “Not deep – relaxed.”

And like she said, she’s already pretty well lubed so my main job is just to massage her asshole – her anus – so it’s loose and relaxed and maybe a little stretched so it’ll be easier for me to go in.

And I don’t know if I’m doing it right – come to think of it, there’s probably a YouTube you can watch – probably a whole bunch of ‘em – that tell you all about how to do it but I never thought of watching any of them. But her muscles do seem to be relaxing and loosening, and her hole does seem to be bigger than when I started.

Also, Helen seems to be liking this loosening part a whole lot, and that makes me think that like when she was putting the lube on my cock, maybe this loosening part could become a whole thing itself...

Then she puts her hand on mine and says, “Ready?”

“Yeah, I’m ready,”

... and all of a sudden I think, “This girl is going to be giving me her ass,” and I get this feeling...

Helen pulls her legs back again and this tilts her hips up – and now her asshole is right in front of my cock.

“Now, Bobby, ” and she gives me this smile, a smile like this is going to be the most wonderful moment in the world.

So I put the slippery head of my cock right against the creamy pucker of her anus, and it’s still a little bit open from when I was massaging it, and I press...

And Helen stiffens herself a little, but it’s not like she’s in pain – more like she’s just bracing herself...

And I’m in. We prepped so well with all the massaging and the lube and stuff that the whole head of my cock slips in on that first little push.

And it was hot! I don’t mean hot like exciting – I mean hot like temperature. I had no idea how hot it would be inside inside Helen’s – asshole, and I got this thought about whether every girl – every girl’s asshole – was this hot or just Helen’s.

And not just how hot is was, but how tight. I mean, inside Helen’s ... inside her cunt ... it’s... snug, I guess you’d say, like being wrapped in the warm, silky flesh. But this – this was like my cock was being squeezed, like it’s being gripped by that hot lining of her asshole. But anyhow, there’s no way I can describe the feeling. Except now that I’ve felt it I know that I want to feel it lots more!

I wanted to know how this felt to Helen. Of course that’s something I could never know, but what I could know was the smile on her face – she was smiling almost like she’s just accomplished something that’s real important.

“Bobby – we did it! We’re doing it, Bobby!”

“Yeah, Helen, we did it – we’re doing it.” And for some reason I got the urge and bent down and kissed the tip of her nose, and that made her smile.

“Bobby?”

“Yeah, Helen.”

“Do you think we could stop for a minute, for me to ... get used to ... to things?” It was like she was apologizing – like she was embarrassed for asking.

“Sure. I mean, of course.” I mean, just because I went in pretty easily, ‘cause we prepared so good and stuff, I know that it must hurt even though Helen didn’t cry or complain or anything.

“Sure, as long as you want.”

Also, if I’m gonna be honest, it felt really good like this, with the head of my cock just inside Helen’s asshole, and the tight grip, and all the heat. And also, there was just the idea, the thought, and in my mind I could practically picture Helen, and my cock inside her ass, and thinking of that made my cock get even harder inside her.

But I guess I’d waited long enough because I heard Helen’s voice.

“Bobby?”

“Yeah, Helen?”

“Can you do it some more, Bobby?”

And again I think, is there’s any nicer way of asking someone to fuck your ass?

Still, in spite of how easy it was to get in her, inside Helen’s ass, I was afraid of hurting her. So I tried to be real gentle when I started pushing again. Except I was surprised how easily my cock went inside her, and it seemed like all of a sudden I was maybe halfway in ... inside her ass.

“How come ... I mean, I thought ... doesn’t it hurt...?”

She saw I was confused and also concerned about her.

“I’ve been practicing,” and the way she said it, it was like she was both embarrassed and pleased.

“Wha...? Practicing? How... ?”

She was still embarrassed to admit what she did, but also she wanted me to know – I guess she wanted me to know how much she wanted it – this.

“Like, with my hairbrush handle...” She stopped, then added, “ ... and maybe with one or two of Mom’s vibrators. And oh yeah, my finger – fingers...”

This knocked me out. Her research, and thinking about it for so long, and the lube, and getting herself “prepared.” I wondered – exactly how long has she been preparing for this?

But before I could think any more about this Helen shoves her hips back up toward me to tell me that I’m not all the way inside her yet and that I should start moving again.