The Photo Shoot

The first picture I ever sent to someone on the internet was to Emily, a girl I'd been chatting with online. We'd met in a chatroom I'd ventured into late one night, feeling bored and lonely. She had done the same. We'd awkwardly flirted. For awhile it was all very chaste, almost embarrassingly so: I'd come home from work at the restaurant I was cooking at, I'd see that she was online and my heart would start beating pleasantly fast. I enjoyed how nervous I got, sending my message, Hey there; how much I enjoyed the immediate pingback, Hey cutie :).

We often chatted well into the night, about anything and everything. The house would darken around me, and I'd sit in the glow of my computer screen, blushing at the playful flirting, unaware of how late it was getting.

I was living at home for the summer; my parents were away on a second honeymoon, but I shared the house with Nicole, the daughter of a close family friend. She was a couple years older than me, staying with us while at work on a summer internship close by. She kept odd hours, came and went as she pleased; when she wasn't working, she was out with friends, and when she wasn't doing that she generally kept to herself in her bedroom. Nicole and I had never been particularly close - she'd been around all the time when we were kids but she'd mostly ignored me, if she and her friends weren't mocking me, and she mostly ignored me now.

Do you have a picture? Emily said one night. I'd love to see what you look like.

My heart leapt.

Let me see if I can find one, I said.

This was when cell phones were just phones. The only way I knew to get a picture to someone was with a digital camera - which I didn't have - or to find an existing picture online. I found one from a family event. It was a little old, but a decent picture of me, one I thought was a fair representation of what I looked like. I cropped it down to just myself and, surprising myself at how nervous I was, loaded it into the chat window and sent it.

Mmm you're cute! Emily said, making my heart jump again.

Thank you, I replied.

No, thank YOU ;)

I'd love to see you too, I said.

You got it. One sec.

She said nothing for a few minutes, and I waited, nervously. I had a picture in my mind, we'd swapped vague descriptions of ourselves early on in our chats, but I didn't really know what to expect. I liked her; I thought I'd still like her no matter what she looked like. But still, I was nervous.

Finally a picture loaded into the chat window, and immediately I smiled broadly. She didn't look exactly like what I'd pictured, but she looked just right for the personality that was coming through in our chats. She was very cute. Short brown hair pulled into a messy ponytail, her big brown eyes shining behind thick-framed glasses. She was smiling sweetly, looking into the camera at a slight angle. She wore a black low-cut top. The picture ended midway down her chest, so I couldn't see much of her body, but my eyes trailed down the smooth skin of her collarbone. Just a slight tantalizing line suggesting cleavage was visible before the picture ended. It was hard to tell, but from the angle of her chest it looked like she might have very large breasts. I stared, wishing the image went on just a few more inches.

You're beautiful, I wrote.

Thank you :), she said.

Then she said, Feel free to use it for inspiration, if you want ;)

What kind of inspiration do you mean? I said, playing dumb, hoping she meant what I thought perhaps she meant.

Oh I don't know, she said. Is there anything it might inspire you to do?

I hesitated, unsure how to answer. This was uncharted territory for me: Emily and I had flirted, we'd verged on the edge of the sexual, but we hadn't gotten explicit. I thought she was inviting me to do so now, but I wasn't completely sure. I didn't want to be wrong and take this somewhere she didn't want it to go.

But on the other hand, I was very turned on. Her picture was sexy, I thought she was encouraging me. And I was fully hard in my shorts.

So I went for it: It's inspiring something in my pants right now ;), I said.

Mmmm does that mean I think it means? she said.

What do you think it means?

I think it means you're hard...

Then it means what you think it means ;), I said.

Mmmmm I LOVE that, she said. What are you wearing right now?

Just a t shirt and shorts. What are you wearing?

I'm wearing the top you see in that picture. And short shorts.

Did you just take that picture? I said.

Yes. Just for you ;)

Mmm I like that. I'd love to see more. I hesitated a moment before sending. I didn't want to push. But I did dearly want to see more. So I hit send.

I bet you do, she said. What would I get in return?

I would love to show you more too, I said. But I don't have a camera :(

Hmm that's sad. There isn't one in your house anywhere?

Nicole might have one, I said. I'd told her about Nicole, how she was staying with us for the summer. I think she does. But she's sleeping now I think.

Hmm, Emily said again. I'll tell you what: I'll send you a little teaser tonight, if I can call you and listen to what you do looking at me. And if you promise to try to borrow Nicole's camera tomorrow.

My heart raced. Giving my number out felt like a big step. The internet had always felt at a remove, almost a separate reality, not fully real. This would make it real. But the prospect also thrilled me.

Deal, I said.

Number first, Emily wrote.

I hesitated only a moment, then typed in the number to my cell phone.

The chat went idle. I looked at my phone. For what felt like a long time, nothing happened. Then, my phone rang.

"Hello?" I said into the phone, self-conscious about my voice, feeling very awkward.

A sweet giggle sounded from the other end.

"Hey cutie," Emily said. She whispered slightly, as if she trying to hide what she was doing from someone, and maybe she was. Her voice was light and airy and sweet. I squeezed my cock through my shorts. "Sorry to keep you waiting," she said. Was trying to get the picture just right."

"Did you take one?" I said.

"I did. Are you ready for it?"

"I am."

"How ready?"

"I can't wait."

"Are you still hard?"

"Yes," I said, my voice shaking. She was driving me crazy. She giggled.

"Mmmm," she said. "I love that I get you hard." I let out a moan. She giggled again. "Okay, it sounds like you're ready."

And then a new image started to load into our chat window. I waited, holding my breath. It seemed to take a long time to load. When it did, I let out another moan. This one was taken more from the front, at a slightly downward angle. I wasn't sure how she achieved that, but I didn't care. She wore the same top, but more of her chest was visible. Her top was pulled low, stretched tight against her very large breasts, which looked on the verge of spilling out. She smiled seductively into the camera, pushing out her chest, squeezing her big tits together with her arms.

"Oh my God," I said. "You're so hot."

"Thank you." Emily giggled. "I'm glad you like it."

"I love it."

"Does it turn you on?"

"Yes."

"Does it make you want to touch yourself?"

"Yes."

"Mmm do it baby."

"One sec, I need to get these clothes off," I said.

"Mmmmm."

I set the phone down, pulled my shirt off, tossed it aside, then slid my shorts down. I sat at my computer, naked and hard, staring at Emily's beautiful picture. I picked the phone back up.

"I'm back," I said.

"Mmmm are you naked for me?"

"Yes."

"I love it. I am too. How hard is your cock?"

"So hard."

"Are you touching it?"

"Yes." And I was, holding the phone with my left hand while my right wrapped around my cock, squeezing and slowly stroking up and down.

"God I love that," Emily said, breathing hard into the phone. "Do you have a big cock, baby?"

"Yes," I said, blushing, hoping I wasn't lying. It wasn't something I would typically brag about, but I was caught up in the moment.

"Mmm I love it," Emily said. She took shuddering breaths. "I'm so wet, thinking about you stroking your cock, looking at my tits. Do you like my tits, baby?"

"I love your tits," I said, breathing hard myself.

"Mmm I thought you might," she said, giggling.

She moaned into the phone. I squeezed my cock, fighting off orgasm. I sat back, listening to her, watching her face in her image, picturing her naked, her big tits shaking as she touched herself thinking about me. It was almost too much; I felt I could explode any moment.

"God you turn me on," she said, her voice almost a whimper. "I'm gonna cum so hard. Are you ready to cum for me baby?"

"Yes," I said.

"Mmmmmm. Where do you want to cum?"

"All over you."

"Yes baby." She moaned. "Cum all over me. Cum all over my tits, all over my face."

I moaned too. "I'm gonna cum baby," I said.

"Me too baby," Emily said, her voice strained, panting. "Cum for me baby. Shoot your load for me baby."

I moaned, loud, and I pumped my cock, and I exploded. My cock pulsed in my hand, and thick shots of cum flew high into the air, coming down all over me. Emily moaned into the phone, crying out in her own orgasm. I moaned with her, and kept pumping my cock, and kept cumming. Our orgasms stretched out together; Emily moaning into the phone just made me cum harder. I covered my chest and stomach with cum. It splashed onto my desk, onto the chair and floor. It coated my hand, my balls, slowing finally as I squeezed and milked my cock.

Emily's breath shuddered into the phone.

"Oh my God," she said finally.

I just sighed, reeling, trying to catch my breath.

"Did you make a big mess for me baby?" Emily said.

"Yes," I said, laughing. "I'm covered."

"Mmmm I love it. I wish I could see. And help you clean up. Can I lick it off you?"

"Yes please."

"Mmmmm." She giggled. "You were loud. Do you think Nicole heard you?"

My skin flushed. My heart jumped.

"Oh," I said. "I don't know. I hope not."

Emily giggled again. "Whoops." I thought I could hear the smile in her voice. She was amused by the idea.

Then she said, "What would you do if she walked in on you right now?"

I laughed. "I don't know. There isn't much I could do. I'm pretty... compromised."

"What would she see?"

I looked down at myself, described what I saw: "She would see me sitting at my computer, looking at a picture of you. Naked, my hand on my cock, and covered in cum."

"Are you still hard?"

"It's slowly going down."

"Mmmm. I love that image. I wish I could walk in on you."

"Me too."

"I bet I could get you hard again in no time."

"I know you could." I thought she might, even without walking in on me.

"Remember our bargain," she said. "Tomorrow. You need to borrow Nicole's camera, and show me more."

"What do you want to see?" I said.

"More."

"Okay. I'll see what I can do."

"Mmm good. I'll let you go get yourself cleaned up. I need to get some sleep."

"Okay. Goodnight."

"Goodnight baby."

All the next day I thought about this. I was pretty sure Emily was asking me to take naked pictures of myself. I'd never done this before. The idea was exciting and terrifying. But I did not have a camera. I thought Nicole did, but I wasn't sure where she kept it, and I was pretty sure she would not be okay with me using her camera for that. But I was determined to give Emily what she was asking for. I thought maybe she'd reciprocate in kind, which thrilled me.

I thought if I was careful I could sneak into Nicole's room, find the camera, do my little photo shoot, and return it before she noticed. I just had to make sure to delete the photos after downloading them to my own computer, or a singularly awkward situation might arise.

So that afternoon, when the house was quiet, I made my move. Nicole was staying in the guestroom, but over the couple weeks she'd been here she'd made it her own. She had a lot of stuff. I started with the obvious places, the top drawer of her desk, her dresser. I did a quick rifle through her underwear drawer, conscious of how awkward it would be to be caught doing so. I thought I heard a sound downstairs and froze, but nothing followed it so I continued.

The search took an uncomfortably long time. I felt like I searched everywhere: her purse hanging in the closet, the backpack leaning up against her desk. Every drawer of her dresser, her desk, under the bed, the shelf of her closet. Finally my eyes fell on the nightstand next to her bed, and its one small drawer. This had to be it. I opened it up, and there were three things, all forbidden: a notebook, a diary or journal I assumed, with a pen clipped to it; a small phallic-shaped device I took to be a vibrator and immediately determined to banish from my mind; and her camera, pocket-sized and teal. Jackpot.

I grabbed it, shut the drawer, and made for the door, and nearly ran into Nicole, who stood in the doorway, looking pissed.

"What the fuck are you doing?" she said.

Nicole was an athlete, tall and fit and beautiful. She'd been the stereotypical hot girl in high school, the obsession of every guy in my class. Blonde, blue eyes, big boobs, the works. She wasn't quite as tall as me, but still in this moment it felt like she peered down at me, hands on hips, looking imperious and intimidating. She was dressed simply, in a blue long-sleeved t shirt and jeans, her hair in a ponytail.

"Uh," I stammered, and looked at the camera in my hand. She looked at it too, and laughed.

"Oh let me guess," she said, "you thought you'd 'borrow' my camera to take some pictures of your little dick, is that it?"

I didn't care for the unfounded insult she'd snuck in there, but still I was struck by how quickly she saw right through me. I could feel my face go bright red and I could make no words come out of my mouth.

"Oh my God," she said, laughing. "That really is what you're doing!"

I shook my head, trying to come out with a denial, but I was withering under her gaze.

"What poor unsuspecting girl are you going to spam with your dick pics?" she said.

"It's not," I started, haltingly. "She's not..."

"Did someone ask to see it?" She was smiling now, amused. Enjoying my humiliation, I thought.

"Uh, yeah," I managed.

"She said: 'Sam, will you please take a picture of your penis and send it to me?'?"

"Well. Not exactly..." Now doubt started to creep in. She had just said "more..."

"Okay," Nicole said, and held out her hand. "Give me the camera, and let's talk about this."

I felt I was at her mercy, so I handed her the camera, and she sat on the bed and padded the spot next to her. I sat, and at her prodding, reluctantly started to recount my developing relationship with Emily.

"So we, uh... talked... last night," I said, starting to hesitate.

"Oh God this is adorable," Nicole said, to my mortification. "So now you're, what, having phone sex?"

"Uh... I guess? We sort of...."

"I don't need the details," Nicole said, laughing. "I thought I heard something, glad to hear that wasn't just you by yourself."

"Oh God," I said, burying my head in my hands. I regretted all of this. I just wanted to get out of this room.

"Hey," she said, putting her hand on my shoulder, being suddenly surprisingly kind. "It's nothing to be embarrassed about. It sounded like you were enjoying it."

I tried to laugh, but it came out wrong. Nicole's subsequent laugh did not. She was enjoying this.

"Okay," she said finally. "So tell me how we got to this camera situation."

So I told her what Emily had said. Our little deal, how she wanted a picture, how she wanted to see...

"More," I said.

"More," Nicole repeated.

"Right."

"That's it?"

"Yeah."

"And you took that to mean... dick shot."

I shrugged. "What do you think she meant?"

Nicole thought about this.

"Well," she said. "You might be right. She probably does want to see it." As she said this her eyes flicked to my lap, just briefly, and a jolt ran through me. She went on. "Eventually. But. You need to have some finesse here."

"What do you mean?" I couldn't believe where this was going. Was she helping me with this?

"Well. You only get one chance. To, you know, show her... all of you." Her eyes ran over me again, and I thought I detected just the hint of a blush creep into her face. "So I think you should, you know, build your way there."

"Okay. So. What does that mean?"

"Men are hopeless. Have you ever heard of foreplay?" She shook her head, looking at me like I was an irreconcilable moron. Then she went on.

"Okay," she said. "This is weird, but I'm going to help you."

"Uh," I said. "Okay?" That sounded immeasurably awkward, but it seemed like she had some ideas, and I suddenly felt out of my depth.

"And besides," she said. "I don't want you going through my camera."

"Ah." That was interesting, and I had to stop my mind from thinking about that too much.

She ushered me into my own room, saying we were not going to do this in hers, and I wondered what exactly she meant by "this." But I followed her instruction, at this point resigned that it was out of my hands. And kind of okay with that.

"Okay," she said, looking around my room, looking a little disappointed. Then she opened up the curtains, seeming to think that improved things, and walked around taking different angles in, like a cinematographer framing a movie shot.

"Okay," she said again. "Let's start simple. Why don't you... yeah. Okay. Why don't you start with just taking your shirt off, and getting in bed. You can pull the covers up so it looks like maybe you don't have any pants on, but we don't need to get that far yet."

Yet?

"Um, okay," I said, and just stood there. Nicole looked at me and started laughing.

"Well come on," she said. "No time like the present."

I hesitated another moment. This was so weird. Nicole was watching me expectantly, and I felt very exposed, even though I hadn't taken anything off yet. And she'd certainly seen me without a shirt on before. Still. And, worse, I was finding myself getting excited about this, and felt a stirring in my shorts which I tried to fight. So, I thought, before that got out of hand, best to get on with it, and get safely under the covers.

So, like taking off a band-aid, I pulled my shirt off. Nicole smiled, looking at me appraisingly.

"Not bad," she said.

Despite myself, the attention was having an effect, and I was steadily getting hard. I was wearing athletic shorts over my boxers, which I thought would not do much to conceal any arousal. So, trying to look like I was not hurrying, I hurried to get onto the bed and under the covers. I situated myself, sitting awkwardly with my back against the headboard, pulling a sheet up to my stomach.

"Okay," Nicole said, giggling. "Is that how you want to pose? Just sitting there?"

I shrugged. "What do you think I should do?"

"You are hopeless," she said. Then she proceeded to give me instructions, leaning in, adjusting the sheet, stopping short of touching me but arranging the shot just so. She took several, from several angles, having me take a variety of poses. She was good. I thought perhaps she'd done this before, and tried not to imagine what was on her camera that she didn't want me seeing. The poses she put me in felt very sexual, very vulnerable, but didn't seem to expose much. I kept my shorts on, but I felt still like the pictures would be very erotic.

"Okay," she said finally, after taking one last picture. She looked flushed as she examined what was in the viewfinder. "I think we have some usable ones here."