Emily and Alfie - Chapter 1

Adult chat room leads to more, much more.

Fresh from the shower, I stood in front of my bedroom mirror, drying my long, blonde hair, getting ready for another boring night on my own. Mom and Dad were out, and I was an only child. I lived a privileged but lonely life. Too shy and timid to be popular. I often spent my time alone in my bedroom, studying, reading, or watching movies.

Once my hair was dry, I removed the towel from my body. My blue eyes glinted at my breasts. I’d recently gone up a size, and was now officially a pert B cup. I ran my hands down my petite frame, over my tummy, towards my unspoiled vulva. I was still very much a virgin in every sense of the word, but I was content with just masturbating.

Eventually turning away from the mirror, I reached for the two-piece, pink satin, pyjama set on my bed. Mom bought it for me, along with lots of other new clothes, insisting that it was time I started wearing more mature clothes. I wasn’t a little girl anymore, though the isolation I lived in constantly made me feel like I was.

I put the shorts on first, pulling the soft satin up my short, smooth legs, the elastic waistband fitting snuggling around my slender hips. I then slipped the matching shirt on and buttoned it up. The revered neckline didn’t reveal any cleavage. I didn’t really have any cleavage, but the fabric did reveal two firm mounds underneath.

With Mom and Dad out of the house, enjoying yet another dinner at a fancy restaurant, I slumped into the creaky chair in front of my computer and logged onto the internet. I browsed makeup, clothes, and accessories, before I found myself gravitating towards an adult chat site that I’d found a few weeks ago. I logged in with the username ‘Emily18’ and started reading.

It was ninety percent sex chat and ten percent people just trolling. I never typed in the main chat. I only replied to one or two men who messaged me in a way that grabbed my attention. It was all a ploy to get to the sex chat, but at least it built a rapport first. I liked the sex chat, reading erotic descriptions from men telling me what they would do to me if they ever had the chance.

A few minutes of being in the chat room, another man messaged me, saying his name was Alfie, and that he was fifty-five. He asked politely if I was ok with chatting to an older man. I told him I was and then our chat blossomed. We talked about life in general, but it was mostly him asking me questions about my life and my sexual experiences.

Enjoying the friendly conversation, taking me out of my own isolation, I relaxed a little too much, confessing to Alfie that I was still a virgin, and I’d only kissed two boys. I also told him how lonely I was all the time. He sympathised and spoke very positively, cheering me up. He even made me laugh.

Then, the chat took a turn. He asked about my feelings on being a virgin, and if I masturbated to relieve my frustrations. I was very open and honest with him, admitting to touching myself on a daily basis. That excited him, which made me laugh again. He then asked how I felt about turning my camera on to see his cock.

I froze in front of the computer. I’d never let the chat escalate that far before. I’d been asked countless times, but it was always a flat no. With Alfie, however, despite his age, part of me wanted to see his cock. He promised I didn’t have to show anything in return, he just wanted to see my pyjamas.

I knew I shouldn’t have done it, but my hand moved the mouse and my fingers clicked the cursor, turning my camera on, revealing myself from the neck down. A surge of nervous excitement coursed through my veins, before Alfie’s camera turned on. His face was also hidden, but he was naked, revealing a tubby, hairy belly and a fat cock.

There was thankfully no sound, because I gasped as I put my hand over my mouth, wondering if I was officially watching porn for the first time in my life. I watched Alfie stroking his erection, for what felt like an eternity, before he let go to start typing.

Alfie55: Wow! Look at you! Those pyjamas are sinful, Emily. Makes me want to touch them. You have an amazing body. Mmm.

Emily18: Thanks.

I typed one word of appreciate, then sat back laughing at the surreal situation I found myself in, had agreed to put myself in. I couldn’t stop staring at his cock. It wasn’t just fat, it was long too, and the head was shiny, causing my vulva to naturally swell and become moist between my thighs.

Alfie55: Do you like what you see, Emily?

I typed back that I did. I was able to be honest because he couldn’t see how red I was blushing, how embarrassed, excited, and curious I was. He then told me how he’d teach me to hold it, stroke and suck it. In that moment, I kind of wished I could have been with him to do it. I was very aroused, but I couldn’t hide my arousal for very long.

Alfie55: I can see your nipples poking through your pyjama top, Emily. You’re a naughty little girl really, aren’t you?

Emily18: I’m a good girl. Lol.

Alfie55: A good girl who wants to be a bad girl, perhaps?

Eyes glued to his cock, watching his hand stroking up and down, my erogenous zones were buzzing, and between my thighs was hot and wet, aching to be touched and pleasured. I was on fire, burning up. I glanced down at my nipples and laughed.

Emily18: Maybe Lol. Are you a mind reader?

Alfie55: No, but I wish I was. You can see what you’re doing to me, and I have a hint of what I’m doing to you. I’d love it if you unbuttoned your pyjama top for me, Emily.

Once again, I shouldn’t have done it. I should’ve logged off, buried my face in my hands and pretended it never happened. But my body wasn’t listening to the one half of my brain that was telling me to stop. It was listening to the other half that was curious, too curious, daring me to do it.

Emily18: I’m not sure I can do it. I’ve never done anything like this before.

I needed more encouragement from him. I bit down hard on my lower lip, watching his cock as his fingers typed. Meanwhile, my fingers curled into the arms of my chair. I suddenly started breathing heavily, and my heart was racing, but I was so turned on.

Alfie55: I don’t want you doing anything that makes you feel uncomfortable, but I want to cum for you. Would you like that, Emily? Do you want to watch me cum for you, baby?

I swear I felt something warm and sticky seep from my body and into my pyjama bottoms. I bit my lip harder, my fingers trembling as I typed without thinking.

Emily18: Yes. I want to see you cum.

Alfie55: Good girl. Now, let me see that gorgeous body of yours. Take off your pyjama top, Emily, and show me your pretty little boobs. I bet they’re amazing.

“Fuck!” I exclaimed at the screen, laughing nervously. “Come on, Emily, you can do this,” I told myself, as Alfie stroked his cock.

With a deep breath, I brought my hands up to the top button on my pink satin pyjama top and undid it. I then went down the front, undoing one button at a time, until all four were free. But I kept the top held together for a moment, trying to compose myself.

I counted to three in my head, then five and then ten, before I slowly pulled the top apart, revealing the pale swell of my breasts, and the tight buds of my nipples, which were hard and sensitive. I slid the top down my arms, quivering as I exposed my chest to a stranger online, a man so, so much older than me, older than my parents, even.

Alfie55: Emily, you’re perfect. I absolutely love your boobs. Don’t be embarrassed. Cup them for me. Show me how you hold them.

As if slipping into a trance, I gently cupped my breasts and pushed them together. No way could I have done it with my face visible. But with my identity hidden, watching Alfie squeezing his hand tighter around his shaft, stroking and leaking, I felt empowered, caressing my breasts on camera for him.

Alfie55: Beautiful and sexy, Emily. Pinch your nipples for me. Show me how sensitive they are. God, I wish I could feel your young tits.

I gasped, my back arching as I obeyed. I rolled my hard teats between my thumbs and forefingers, gasping more and more. Pleasure raced through me, forcing me to open my legs under the computer desk.

Alfie55: That’s it, Emily? Are you wet? Is your pussy aching? Tell me, baby. I bet it is.

I released my breasts, leaving them to rest high on my chest, and typed back the truth. I told him I was wet and needed to come.

Alfie55: Show me, Emily. Take off your pretty pyjama shorts and show me how wet your little kitty is. God, I’m going to cum soon.

I didn’t reply, but I did hesitate as my tummy churned violently with fear and excitement. Then Alfie rubbed the tip of his cock with his thumb, smearing his pre-cum around. It was like a magnet to my eyes. I couldn’t look away. I wanted to see him ejaculate so bad.

Standing on shaky legs, I didn’t think about what I was doing, I just did it. I hooked my thumbs in at the sides of the waistband, and pushed my pyjama shorts down my legs. I leaned forward to get them over my knees, absently and foolishly revealing my face as my breasts jiggled. When I realised my error, I saw I had a new message from Alfie.

Alfie55: God, your so pretty, Emily. You really are perfect. Show me your tight little pussy, baby.

Putting my mishap behind me, I stood with my arms by my sides, not sure what I should do. I tilted my hips forwards and glanced down, showing him what he wanted to see, trying to imagine what he was thinking.

Alfie55: Perfect, Emily. I want to lick it for hours. I love a tight, shaven mound. Spread the lips for me. Show me how wet you are.

Standing in front of my computer, my naked torso on display, I felt my legs shaking. But I did it. I used my forefingers to peel apart my virgin sex lips. Touching myself made me gasp and quiver, then I gasped in shock, at the realisation that I was showing him my most intimate body part. Pink and wet.

Alfie55: Yes, Emily. Look at that perfect little cunt. My cock would feel great inside you. Touch yourself. Show me how you make yourself cum.

I moved my left hand to my side, but the right one hovered over my hairless mound, my fingers trembling with both anticipation and trepidation. I’d only done it under my bedcovers and in the shower. I took yet another deep breath and showed him how I liked to touch myself, how I rubbed my clit.

My eyes began to drift closed and open as I masturbated for the first time on camera. Someone was watching me. Someone was masturbating in time with me, wishing he could fuck me. Without thinking, I brought my left hand up to my breast and cupped it.

I became lost in my own world, rubbing my hard bud while I squeezed a breast and tweaked my nipple. I started panting, trying to keep my eyes on the screen. Alfie was stroking faster, his podgy, hairy belly rising and falling as he pleasured himself over me.

It was intoxicating. Then I felt my orgasm building and building. I raised one leg and placed my foot on the chair, spreading my sex so I could rub my clit faster. Alfie quickly stood up, stroking his cock at the screen. It filled it, pushing me closer to the edge.

I don’t know how long we performed for each other like that, but when I saw his sperm start ejaculating, I convulsed in my own orgasm. I gripped the desk and kept rubbing, filling my bedroom with the sounds of my ecstasy. When it was all over, I quickly turned my camera off. Alfie did the same.

Alfie55: Are you ok, Emily? Don’t be embarrassed. That was incredible.

I put my pyjamas back on but kept the camera off. I really wanted to log off and shout my computer down. I was terrified.

Emily18: I’m fine. But I have to go. Bye, Alfie.

I didn’t wait for his reply. I logged off, shut my computer down, and hid under my duvet. My body had never felt so satisfied before. I eventually started laughing and went downstairs to make a drink, vowing to never visit another adult chat room again.

But the next night, while my parents were downstairs with some friends having a drink, I logged on again, roughly around the same time. I almost gave up trying to find Alfie55, but then he popped up in my private messages, asking how I was. He said he was concerned with the way I left.

I didn’t yet know it, but I was on the road to becoming addicted to showing myself on camera. I needed another orgasm like the one I experienced. There was nothing like it.

We talked about the night before, and once Alfie knew I was ok, he took control of the situation again. I tried to tell him I could only chat because my parents were home. But he had a way of reading my mind, so it seemed.

Alfie55: Lock your bedroom door and take off your pyjamas, Emily. You know you want to. I’m going to cum for you again.