This is my first post, please let me know if you enjoy it or have suggestions, I would love to commiserate with other writers and readers. All rights reserved.
Babysitter
I had been watching Paul and Nicole's two children for a while. She was very pretty, about 5'8", nice legs and loved to show them off. She towered over my 5'6' in her heels, Paul was about 6'1 or so, clean shaven and a trim wide shoulder athletic build, they made a very good looking couple. They would go out, she in a sexy dress and heels, and he in nice pants and shirt, or a suit sometimes dancing or parties I guess, I never really cared. It was a cool gig, the kids were young, and went to bed around 8 or so, so I had lots of time to myself. One of the best things was she would have Vanity Fair, Cosmo, that sort of thing in the coffee table. I would go out back, smoke some, and jack off looking at the pictures, of the models and ads, even reading about guys and sex, pleasing your man.... I would see a sexy dress, or shoes, etc and wish 'why can't I be you?'
My sister was a couple of years older than me. I had been dressing in her clothes and wearing makeup for some time, she was actually the dream girl of my friends, but as she is older she was unattainable for them. Maybe that's what I subconsciously thought, that I could be as attractive to my friends/guys as she was when I dressed up? ... She had gone away to college the fall that this all happened. I was a bit smaller than her as well, so I loved her dresses, skirts, and especially her shoes. I loved how sexy I felt in panties, stockings, with a tight dress stretching against my waist, butt and legs, my eyes and face lightly done, my hips swaying with the heels as I walked, danced, bending, twisting and squatting poses in front of a mirror. My ankles soon got used to wearing heels, her sexiest were 4.5 inch silver ankle strap sandals. Most of her pumps I could easily slide into as well..
One of my favorite outfits was a plaid shortish skirt, white blouse and these really sexy white lace anklet stockings with her red 4 inch strap sandals. Another was a white lace bustier that showed off my flat tanned tummy, red bolero jacket, matching red skirt, and of course red pumps. Man, she had it all for me to play with. I'm a dark brunette with hazel eyes. My hair was feathered back, a little past my shoulders with long bangs that I can do many different looks with, oh and I was able to get a really deep tan that summer. My mom and sister (my dad had died when I was quite young) left me alone quite a bit during the day as they had to work. My sister and my mother as well would always be buying new shades of this or that, and never seemed to notice that the makeup was either missing or used up more quickly I had lots of time to practice getting my eyes and lips just right, a couple different looks, and lots of practice taking it all off quickly.
Make up was easy to buy too, I would be buying a "gift for my sister", who has the same eyes as I do, same complexion, etc. Maybe show a picture of her and if nothing else, get a free lesson on shadow for our eyes, what lip color, etc.
So of course I started looking for Nicole's clothes when the kids had gone to bed. I found heaven! She had a walk-in closet, so many pretty dresses, sexy skirts and a lovely collection of shoes. At first I would just look, touch, and eventually hold them up to my body in her mirror. I began to wear my favorite lace thong under my jeans to their house (it keeps my um, thingie, lol hidden well when it gets excited). And yes, then I started trying her dresses on. It was just quickly at first but they were out late usually. I also started bringing a bra and some stockings and a make-up clutch in my computer bag and would put a touch on my eyes and lips. I was so paranoid at first and would only stay dressed for as long as it took, then make sure I cleaned my face and hung everything up so all would be "normal" when they got home around 1am or so. But as you know, as time goes by, we get a little bolder, so I got to wearing a sexy dress or tight skirt around the house in her heels, imagining I was one of the models in the magazines playing pool at a party in the basement bar area (some nice big mirrors too!), dancing around, posing and flirting in the mirrors, etc. .
One particular night I decided on a mini black cocktail dress, black pumps, icicle dangle earrings (mine!), a couple of silver bracelets and a little choker style necklace. I love how my bare shoulders and arms, and well, cleavage look in black with my dark tan. I love this dress as it has an open back and loose neck that hides my lack of breasts. It also shows lots of thigh! I slid the dress on, it had the distinct aroma of her Eternity. And there is something about putting dangle earrings on too, my eyes seem to sparkle more. I felt so pretty and very feminine, I imagined I was getting ready to go out clubbing! I slid into the pumps, about four inches, and although I thought I looked sexy with my bare tanned legs I thought that next time I'll paint my toes and wear a pair of her strappy sandals. I decided to look a little more elegant tonight and took black thigh highs out of my bag. I loved watching myself in the mirror as I slid the stockings on, then the pumps, the feel of my hands sliding up and down my now sensitive legs smoothing the stockings, wondering what it would be like to go shoe shopping..... What would it feel like to have the salesman touching my ankles and calves through the stockings... Would he think I was a girl? Would he get a little tingle in his pants? would I? Would he ask me out? As I walk down the stairs I imagine I am walking down into a nightclub, slowly, sensuously, heads turning my way, I feel the eyes on my legs and butt.
I was finishing up my lashes at the bar downstairs and crap! the door to the garage opens. Paul looks in as I turn having a panic attack, Nicole's going to kill me, I'm so busted, my clothes are upstairs, shit, he's going to beat the crap out of me, everyone will know now, my mom! etc all doom and gloom rushing through my head in that instant, my clothes are upstairs! nowhere to hide, or run, too late! as well as my face probably turned white as a ghost! ..
He quizzically looks at me, then a look of recognition.
"Amazing! .... I thought you were your sister for a second."
I'm not sure who was more astonished, but I was still mortified! Holding my breath, shaking, feeling faint. .Hoping I just poof, disappear.
"I'm sorry, so .... oh, um..." I blurted out, holding my hands to my face. I was too scared to even cry, speechless, and then wondering where Nicole was..
He must have been able to see the panic, he took me by my shoulders and said softly "It's OK, It's ok, relax, don't worry, she's asleep in the car, she won`t know."
He didn't know what to more to say, then "I guess the kids were no trouble"
I nodded my head, glad for the change in subject, then shook it, the earrings dangled. :"No, just fine" I was able to gasp.
"You're not mad?" I whisper looking at the floor
After a second, which seemed like eternity, he said '"No, you look good. yeah, with your sister around I guess you know what to do. but I'm just surprised, pleasantly, no, not really surprised I guess."
Then he shocked the hell out of me and said "You might as well finish freshening up while I take Nicole upstairs. She's kind of passed out' Then he stammered "You really do look like a version of your sister, that dress fits you well"
"Seriously, we can play pool or something unless you need to get home early, kind of a wasted night, early," he still couldn't speak right, but all I could do was nod my head.
I'm still shocked and can't move while he opens the door, blocks it, and next thing I see his Nicole in his arms, light, like a feather, so gentle, but seemingly unconscious.
He whispers to me "Go ahead, make yourself at home, you're safe here, no one will know", and with a weird smirk "especially not this one!"
And then the clincher: "I could use the company, it's way too early, it'll be fun."
And for some reason that gave me so much relief. So what the heck, not sure if I was just relieved, or did I really think that this was a chance I shouldn't pass up, to be with someone? I know I was so relieved that someone I trusted finally knew my secrets, and didn't seem to mind.
I finished my lashes, and put on pink lips and gloss, wondering what the hell am I doing, but he did tell me to go ahead, and we get along well anyway, so I took the balls and racked them.
So he comes downstairs,
"Glass of wine? I need to unwind, dang what a strange night, you could probably use one, you're still shaking".
"Sure, please!" I nod. "You really scared the crap out of me, I wanted to run, hide, disappear!" I really needed something to calm me down.
"Sorry about that, but can you Imagine my surprise, coming into my house and seeing a strange young woman?"
I laugh, "I guess", then I add playfully "so you think I'm strange?"
He smiles "Um.. an interesting surprise, you' really are pretty like your sister, pretty eyes."
I'm thinking now here I am, just a guy, I'm wearing one of the sexiest dresses I've ever seen, earrings, high heels and this man is telling me I'm pretty, I'm so overwhelmed, but I notice how much larger he is than me. His eyes linger on mine, I blush, I kind of look down and just say 'Thanks" then demurely look up, smiling into his silver/grey eyes, so striking, I felt like I could fall into them....
He breaks the moment "Lets play some pool":
I love how the heels make me taller, stretch my ankles, add a wiggle to my hips as I saunter around the pool table. I begin to realize how comfortable I am all dolled up with him, my second nature feminine movements and mannerisms have come out, and dare I say I'm a little bit flirty. He's funny, and makes me feel at ease. We joke and laugh at a lot of things. I start to notice things about him, how his strong shoulders and chest taper down to his waist, strong looking arms and legs, good posture and nice pants, yes, I do notice his firm butt. And again that he is so much bigger than me!
He asks me if I have a boyfriend........
"No" I shake my head, laughing.
"Not yet, anyway" he smiles "You should get out more, lots of guys would love to have you to show off."
I'm not sure what to make of this, but I'm happy for the compliments, and his personality helps to calm me down.
"Thanks for asking me to stay, It's more fun playing with you here than by myself" then I laugh, "but I usually don't drink when I'm on the clock!"
We stand closer and closer at each opportunity. I feel his eyes on me when I bend over to shoot, and smile when I catch him, pull my hair behind my ear. I feel so free I dance around a little when I make a shot. I love how the dress hikes up my thighs as I bend to take a shot, standing one leg straight, one bent, and know he's watching me. I am exaggerating my hips a little when I walk, my posture enhanced by the heels, love how my hair feels on my bare neck and shoulders when I turn. and the tightness of the dress on my waist, butt and thighs. Of course I'm getting a little worked up, my nipples even feel tingly against the softness of the dress. His hand held mine as I held the wine glass up for a refill, our eyes meet again, and I know I'm blushing because his face is becoming very pleasing to look at.
I decide we need to share his cue stick, and walk over close to him. I want him to hold me tight against his body in those big arms. I so want him to kiss me now!
I feel him suddenly next to me, he slides his fingers on the inside of my arm, entwines my fingers in his as he pulls me closer. I feel his warmth as I stumble into him (I'm a klutz sometimes, but I was hurrying!), lean forward and lift my face up lost in his eyes. I close mine and feel his lips slowly cover mine, his hand on my waist pulling me tight, the other sliding up from my waist to my breast, palming my nipple through the dress. I wish I had breasts I think, but his touch sends tingles through me and I'm lost in his lips. I fold into his arms, his hand feels like it is grasping halfway around my waist it is so big, then he slides it down to pull my hip closer as our lips work together. Being kissed by this attractive man, his hands all over me, in the sexiest dress I've ever worn, in stockings and heels...... that excites every nerve is almost too much, I feel my dick struggling against the panties, wondering if he feels the same, if he knows what he is doing to me.. Thinking I'm just going to cum right now!
Our lips unlock, and he looks in my eyes. I gasp smiling "mmm that was nice."
He gently pulls my hair back and slides his lips up my neck, causing shudders through me and gasps, then kisses up under my cheek and he nibbles on my ear. My mouth open in a silent gasping moan it feels so good. He's leaning against me and me against the pool table and my stockinged thigh rubbing on him and his thigh between my legs and him kissing my neck, he pulls back looking at me with those eyes...
and I cum, alot, and again, gasping for breath, soaking my panties, my hips humping against his thigh, staring into his eyes. Gasping, mouth wide open, he held me tight, my eyes rolled back in my head, I think I fainted with pleasure. He leans in and kisses me gently, holding me tight as I catch my breath, my shuddering subsides
My hand slides up his chest, wow, what a thrill. I've never felt this way before. Having him watching me cum and holding me released so much energy? fear? relief? Inhibition! I open my eyes halfway as he looks down at me with those incredible silver eyes, then begins to kiss me more aggressively, his lips hard against mine. Then his tongue parts my lips and I'm floating away again as I accept his tongue in me and want to kiss him forever as he grabs my butt with his huge hands and pulls me tight. I have to gasp as I think I can feel him through his pants up against my tummy. As his tongue explores my mouth, tingles against my own.
He puts his hand to my cheek and says "Look! ever thought you'd look like this?" and turns my face to see us in a mirror. There I am, folded against a man, my little body against him, his hand covering my butt, my dress hiked up my thighs, my legs look sexy on my toes in the heels and my hair a bit tussled. I lean back from him, his hands holding me up by my butt, and I whisper, "You look so good too". {I can't believe that has come out of my mouth! but he does, and I feel so warm and vulnerable, sexy and available, that I need this man to, to. To what?, he saw me cum, we share something now, and I'm getting really horny again) I slide my hands up his chest palms on his nipples (his muscles are really beginning to turn me on so!) slide my wrists and elbows around his neck and stand up on my toes to kiss him hungrily. sticking my tongue through his lips. He twirls me around to face the mirror again, rubbing up my sides to caress my "breasts, kissing my neck and shoulders so I can see how sexy we look together. He slides his hands down my waist to my hips.
"Do you have a boyfriend now?" he whispers into my ear.
Every nerve in my body tingles, he's driving me so nuts, mad with desire.
To answer him, I reach my hand back over my head to pull his face closer as I twist my neck back to kiss him and it just happens, I gasp as he holds my butt against his hardness. I freeze in place! I feel so close to him I would let him take me back there, I think I want him to, I want him to fuck me! He puts his hands on my hips and grinds softly into my butt as we sway together, him kissing my neck and shoulders, me just melting. He takes my right hand in his and slides it between my butt and his cock, grinding into it. I'm about to die, feeling another man's hard cock for the first time. Especially knowing that I'm the one who made him hard! I know I'm past the point of no return now, and I really want to touch it, see it, so I turn to face him and slide my hand down his tummy into his pants. (my own is rock hard as I touch his)
"Oh Paul" I gasp. There is alot of cock in there, it feels hot, fleshy, kind of like mine I guess, but way thicker, longer, and not mine! I don't think it's really really hard yet. I grasp it lightly, and pull it up, softly stroking it as I kiss him. I'm about to jump out of my skin.. Unbelievable, I'm kissing a man while stroking his dick! He undoes his pants with my hand in there, and it is free.
I smile at him looking in his eyes and whisper "Will you be my boyfriend?"
"What would my girlfriend do?"
I smile so much, nod, and slowly squat down on my heels, mesmerized by the cock I'm holding, it's getting harder in my hand. And that is a sexy thing, him getting hard for me, just at my touch!
I must have been staring as I looked at the cock pointing at me (I remember the first time I really noticed another guy's dick in the locker room in jr. high, Kevin something, never thought I'd be this close to one)
"It's yours" he said. then "You've never seen one up close I guess", more statement than question.
I'm thinking I have to paint my nails next time as I slowly grasped it and pulled the skin back from the head. then I was rubbing the thick vein underneath with the tip of my thumb as I noticed the drips forming on the hole. I rubbed them underneath and around the head with my thumb, he gave a little gasp and his cock jerked. I squeezed some more out on my thumb then took it and curiously licked it. I looked up at him and he smiled, then "that's so fn sexy".
I never dreamed I would be doing this!! I leaned in to suck the drips into my mouth to taste more, sucking only the tip of the head, like a thick straw. Now I'm not sure I can fit it in my lips. I pulled off and licked underneath. I was entranced by this hard veiny thing, much bigger and thicker than mine, if you must know, about 8, 9 inches I guess, and I couldn't put my fingers around it. I stroked it down to his balls and wanted to touch them too. Looking at him I rubbed the head on my cheeks, under my chin, and my lips, kissing underneath, it felt so sexy rubbing the tip of the head on the inside of my lips, getting it wet. Then slid my lips and nose down the shaft to his balls, stroking it, pulling the skin tight nuzzling the balls with my lips and chin. I felt so sexy with his hard cock on my nose and forehead!
"You're driving me crazy!" he gasped, "put it back in your mouth."
"Is that what you want your new girlfriend to do? You like me down here?"
He chuckles "yeah, you look so sexy down there, such pretty lips!" he reached down and slides his hand over my hair. He has unbuttoned his shirt, I wanted to kiss up his tummy, his chest, but I so wanted to please him. And he had his hand on my shoulder!
I shook my hair back and began kissing the tip, then sucked the head into my lips, clamping on it and trying to suck it off the rest of his cock. Then I opened wide and it stretches my lips as I slide it in on my tongue, clamped my lips tight and began to suck it in and out, licking it inside my lips. I loved the head rim coming out of my lips and back in, the feeling of it sliding through my hand, my lips, on the roof of my mouth, then back to my throat. I was trying to bend it as I worked it in and out, sucking. I had to pull it out and look at it. I couldn't believe I was really sucking his dick. And enjoying it, I feel so sexy wearing a sexy dress, heels, with my man's cock in my mouth. And admiring his body from down here. I cupped his balls with my other hand and rubbed gently, just amazing, I slipped it back in and looked up at him, as he gently took hold of my head and began to thrust softly in and out, slowly working it to the back of my mouth, I try swallowing against the head, but it wont fit. He thrust a little harder, more quickly. I hold on to his powerful butt and thigh, as he tries to get it deeper in my throat, I happened to glance over at the mirror, can see my face with a big cock sliding in and out, so sexy squatting in my heels, my dress up around my waist, I sucking my boyfriend's cock! I'm so hard, I have to feel his strong butt, I slide my hands up his thighs and six pack tummy. I squeeze my thighs together and as he begins to take long slow strokes, holding my head, fucking my mouth, my own orgasm builds. I don't think I've ever been this hard.
"I want to watch it" I somehow groan. and rubbing my thumb underneath the head stroking it tightly, rubbing it on my chin it erupts. I know I jerked my head back a bit as it landed on my cheek and lip, but I keep stroking it, and it jerks and shoots a big one up my cheek, then a few more times. Half in and out of my lips. I look at him, trying to pump more out of his cock. I'm sure I was ear to ear grin, I made him CUM!!!!! He has this look of oh, satisfaction? happiness? bliss? He takes his cock by the base and rubs it around my lips, my cheeks as I kiss and lick. I have to reach down and rub myself through my panties and I explode gasping as he rubs his cock on the cum on my face. Humping my hand I shoot load after load as he sticks the head in my moaning mouth.
I slowly stand up, still shaking from my orgasm, my hands on his chest. he holds me tight. I want to kiss him but I tell him I should clean up first. I just am smiling so much, so happy, really just amazed that I could make him cum. He tells me I look sexy when I have just been ravaged! I feel so warm and feminine, sexy and complete, as I pull my dress down and float off to the powder room in my most sensual walk. I grab my makeup clutch off the bar and I feel his eyes on me, my legs, my ass.
Hey! he says.
I turn coyly looking over my shoulder, run my hand through my hair.
"I don't even know your name!"
I give him my sexiest wink and close the door.