Mr. Cinderella: Open Letter to a Shy Boy

Shy Boy, I could have rocked your world. I suppose you were a good friend, to leave with your drunk roommate and get her home safe. But if you had stayed, and played your cards right, you could have left with me. Instead, I had to go home alone and enjoy my naughty thoughts by myself.

I had seen you come in, and pegged you as shy right away. You had that look, stealing glances at people as you lifted your beer to your lips, but otherwise, you were sticking close to your friend. Until he left and you were on your own. I watched you finish your beer and get another before you slowly made your way into the crowd on the dance floor. And I was impressed that shy as you were, you were willing to dance by yourself.

But I knew, Shy Boy, that you’d have trouble approaching me head-on. When you finally worked your way to the edge of my group of friends, I maneuvered myself immediately over to you. And promptly turned around so you could look at my ass as I danced. I gave you the opportunity to dance behind me and slowly reach out a hand and touch my hip. I let you make that move with my back to you, so you didn’t have to risk being rejected to your face. Not that I would have done that, of course. No, I pressed my ass against you, made your cock stir, and felt your other hand grab me, too.

I turned around, and we danced for quite a while, Shy Boy, but you wouldn’t meet my eye. I started to get concerned that maybe you weren’t just shy. Maybe you were trashed out of your mind and unable to focus. Maybe you were a sociopath and couldn’t connect through eye contact.

So I called you out on it. I leaned in and spoke into your ear, and though it was dark, I’m pretty sure I saw you blush. When you spoke, your voice was husky, and I figured you had been on T for few months, probably not much longer than that. You gave me a really cheesy line, but it seemed sincere, and I laughed, but didn’t laugh at you and you flashed me a terrific smile and I started to think about kissing you.

And I started to dance even closer to you, wanted you to picture me moving like that naked. And maybe you did, because your fingers dug into me. I reached down and squeezed your leg and thought about inching my hand upwards to your dick.

And all of a sudden, you had to leave. Your eyes pleaded with your friend to handle the drunken situation on his own, but he needed you to help get her to your place, and I kissed you a few times and you nibbled at my lip and you were gone. My very own Mr. Cinderella.

But later, as I lay in bed, I ended the night with you.

You invited me to come with you and your friends. After finding out where you lived and passing on your number and address to my friends, I joined you all in the car. Drunky was in the front seat and you and I sat in the back while your sweet responsible friend drove. I leaned over and whispered in your ear.

“So, what’s your name? You laughed and I got that great smile again.


“Aiden, I’m Allison. Very nice to meet you.

I was sitting close to you and put my hand on your leg. You weren’t sure what to do. You were too shy to touch me, even though you were pretty sure it would be okay. So you sat there and watched my hand slide ever closer to your cock, stopping just short of inappropriate-around-your-friends touching. I could feel you tense beside me. Tense in a good way, with your breath quickening and your heart starting to skip a little.

And Shy Boy Aiden, I figured that you were shy about a couple of things. I figured you were shy just because. Because you were a Shy Boy. But I also thought you might be shy about the new way that people were seeing you. Shy about your bound chest, shy about being with a stranger who didn’t know exactly how it was okay to touch you. Shy about a straight-looking girl maybe wanting to do things you weren’t sure if you’d know how to respond to.

But I knew that I could make you feel good. And I knew that figuring out how to touch you just right –taking my time and teasing us both– would make me drip.  At the club, when we danced and kissed, you responded so well to all of my little cues. You leaned closer into me when I put my hand on your chest or ran my nail along your neck. You kissed me harder when I gave your hair a little tug. But you waited for me, you didn’t make any moves or do anything like that yourself. I could tell that you would be respectful and appreciative of whatever I had to offer. And the fact that you weren’t an asshole, didn’t feel that you were entitled to sex, made me want to give you an amazing night.

When we arrived at your house, you helped Responsible Friend get Drunk Roommate up the stairs. As soon as she was in her bed, you came back over to where I was hovering in the front hall.

“Sorry about that. Thanks for being so understanding. Um¦ You trailed off, wanting to bring me to your bedroom but not wanting to ask.

“No worries. I think it’s nice that you watch out for each other. So¦do you want to sit down? In the living room? Or your bedroom?

“Um, yeah. We can go to my room. You led me down the hall to a cluttered but neat room. Your bed was made, you had books around. It was a room I’d be interested in exploring. Too bad I’d only be in town for the weekend.

I shut the door behind me and you stood in the middle of the room, looking at me. I appraised you. You had turned a small light on as we came in, and I could see you better now than I had been able to all night. You were as cute as I had initially thought. Slightly taller than me, a cute black button-down shirt and jeans that fit very nicely. Great eyes with long lashes I was jealous of. Nicer than mine, even though I was wearing mascara.

I gave you a big slow smile, and you looked down and grinned. I took a few steps closer to you, leaned in, and gave you a deep kiss.  You responded just the way I like. You pressed yourself into me, your hand at the small of my back, pulling me into you. Your tongue explored my mouth in just the right way “ not too insistent, but interested. I felt myself getting wet with just those kisses.

I pulled away from you and motioned to the bed. You nodded, and sat down on the edge of it. That was perfect, because I was able to straddle you, wrap my legs around you, and kiss you some more. As our breathing got harder, I knew that your cock was getting hard as well. So I pushed you back and got on top of you, grinding against you. You moaned and leaned your head back, eyes closed. I sat up and pulled off my shirt. Your eyes opened and widened a bit. You hesitantly reached a hand up to touch my breast, running your hand over my lacey bra. I leaned forward slightly, allowing you to cup my breast in your hand.

I let you explore my tits with your hands for a while, and then lay down alongside you. I ran my fingers through your hair and pulled you in for a kiss. Your kisses were more insistent by now, and your hands were all over me, squeezing my ass, toying with the waistband of my jeans. I slid my hand over your chest, down along your body, and squeezed your dick. Your hips thrust up into my hand, and I started stroking you through your pants. I loved the feeling of you in my hand, straining against your jeans as I rubbed you.

I paused to unhook my bra and slip out of my jeans. I wasn’t wearing underwear, and you were shocked to suddenly have a naked girl next to you.

“I think we should get some of your clothes off, too. Is that okay?

“Oh, yeah. Of course. You sat up and pulled off your socks and shoes, giving me sideways glances. Your shirt came off next, though you kept your undershirt on. You paused, and I could tell you weren’t sure if you wanted to take off your pants.

I crept closer to you and kissed the tattoos on your arms and shoulders. I got behind you, pressing my tits against your back, sneaking my hands around you and squeezing your legs.

“You are really fucking hot, I whispered in your ear. “And do you know what I want to do more than anything tonight? I want to suck your cock. I want you to take your pants off, and lie down, and just trust me. I want you to feel my mouth on you, feel my tongue on your balls, and I want you to come in my mouth. We’ll go really slow, and you can stop me at any time. Okay?

I could feel you swallow. “I would really like that, too. But I don’t know. I haven’t had anyone¦.

“It’s okay. I get it. And I know that you just met me. But I can feel how hard you are, and I love sucking cock, and I will go slowly. And if you want to stop at any point, we will. And if you decide you want to strap on instead, that’s okay, too. For now, let’s just get those jeans off.

You twisted your head around to look at me. I smiled at you, and you kissed me. I pulled back from you and stretched out on the bed, as you slid your jeans off. I motioned for you to get on top of me, and I wrapped my arms around you. We made out for a while, as you got relaxed again, and grinded against me. I reached down and grabbed your cock through your boxers. You groaned, loudly, and I pulled your hair a little.

“Roll over. You complied, and I got on top of you and kissed your neck. I could tell your neck was sensitive; you arched your back and held me close. I moved to your shoulders, then down your arm, to your wrist. And then your hand. I licked at your fingers and you moaned. I slowly slid one finger all the way into my mouth, sucking hard. Then two fingers. You watched, eyes bright, as I sucked on you.

Then I grabbed your hand, held it tight, as I moved my face towards your boxers. I could smell the musk of you, and it made me drip. Literally, I could tell that I was dripping onto my legs and before long would be dripping on your bed.

I kissed your legs, as much of your thighs as I could reach, pushing your boxers aside. I made my way to your waistband and pulled it down slightly, running my tongue along your skin. You shivered slightly. I looked up at you, and you were looking back at me, watching to see what I would do next. I slowly positioned my face at your crotch. I lowered my mouth to the thin fabric separating my face from your cock. I breathed on you through the thin damp cotton.

You groaned, loudly. So I pressed myself against you, letting you feel the pressure of lips against you. I could feel and see your hard stiff cock through the fabric. The testosterone had made it big enough for me to suck, to snake my tongue around, to bob up and down on. And that was exactly what I was going to do. But not yet. For now, I just licked you through your boxers, then kissed you through them. And then I started to bob my head up and down, so that you could feel my mouth intermittently. And I knew you were watching me, my head bobbing, and that it was fulfilling your fantasies. That you were finally experiencing what guys in the porn you watched got to experience. Some random girl from the club coming home with you, getting naked, and sucking your cock.

Now I was dripping onto your bed. And I wanted your boxers off, your cock in my mouth.

“I want your cock in my mouth. I tugged your boxers off, and you didn’t resist. “But first, I want you to feel this. Feel how much I enjoy giving you head. I grabbed your hand, and touched it to my pussy.  It was more than wet. Liquid was flowing from me, sliding down my legs.

You gasped, shocked. “Oh my god. Oh my god, you are dripping onto me. You just looked at me, amazed. I smiled. I like how wet I get, like knowing that people can see and feel exactly how much they turn me on.

“See, that’s because you are so hot. The way you kiss me, and the way you move, and your body, and your cock. All of that turns me on. Now lie back down. I’m going to suck your dick.

You complied, rubbing your fingers together, still enjoying the wetness of me. I kissed your thighs, then licked your balls, and you moaned. Then I moved up to your cock, kissing it lightly. You reached for my hand and squeezed it hard. I licked you, swirling my tongue around your head. And then I lowered my mouth onto you, taking your whole dick into my mouth and sucked gently. Your hips matched my rhythm as I slowly moved up and down on your cock. I could feel it getting even stiffer than before. I found your other hand, and placed it on the back of my head. I knew you’d be gentle, that you wouldn’t pull my hair too hard, wouldn’t try to choke me with your cock. I wanted you to be able to control my speed, wanted your fingers tangled up in my hair as I gave you head.

I started sucking harder, massaging you with my tongue, and you pushed me down onto you. I could feel you getting closer, feel how rock hard you were, feel you start to tremble.

“Oh god, you said, slightly surprised. “Oh, god, I’m going to come.

Around your cock, I murmured to you, “Come in my mouth.

And you did. You came hard, one hand squeezing my fingers, the other in my hair, holding my face against you as your back arched and you cried out. Your body thrashed from side to side, and I kept my mouth on you, using my arms to keep from getting crushed between your muscular thighs.

As your body became still, you pulled me up towards you, and wrapped your arms around me.

“Thank you. How did you know exactly what to do?

“Instinct? From the moment you started dancing with me, I knew you would enjoy a good blowjob. And I wanted to give you one.

“Well, thank you, Allison. That was¦amazing. Is there anything I can do for you? You’re so wet.

“No, I got exactly what I wanted. And¦I’m so sorry to do this, but I feel like I should probably leave soon. I don’t want my friends to worry about me if I don’t turn up.

“Um, okay. I know you mentioned when you gave them my info that you were just visiting. Are you here for long?

“I leave tomorrow night. I grabbed my phone and called the number you had given me to pass on to my friends. “Here, I’m calling you. If you want to try to get together tomorrow, now you have my number. And if you’re ever in the Bay Area, I’d love it if you got in touch.

“You’re awesome. I absolutely will. And not just because you give great head.

I laughed as I pulled my clothes on.  You grabbed your keys and waited outside with me while I called a cab. When it pulled up, you gave me a lingering kiss before shutting the cab door and going inside to bed.

¦Shy Boy, that’s what you missed. What we missed. That’s what I had to entertain myself with in bed that night, fingers on my clit.  Next time, get my number before running off.


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