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Hmmm, where to start? I'm Andrew, but Andy to most everyone that knows me. I'm in my senior year, looking forward to taking a couple of semesters off, to work and build up some cash, before hitting college. I've been mowing lawns, trimming, etc for three years now, and doing ok. Really, in the last few months, better than that. A local Doctor ( Dr. Green) posted that he needed a new yard guy, so I applied. When I saw all the guys that were there, also looking for the job, I figured I didn't have a chance. Much to my surprise, the next day, the doctor's wife called to say she'd like me to come over for a second interview. Maybe because the doctor interviewed me first, and he wanted her to confirm anyone.
When she answered the door, my tongue hit the floor. I'd heard the term "milf" before, but until now, never saw anyone that qualified. She was super model quality, an eleven out of ten. Tall, slim, tan, decent rack, slim waist, firm bottom (She was wearing a little bikini that hid very little), and legs, OMG. Anyway, she led me out to their pool, offered me a lemonade, and had me sit in a lounge chair across from her chaise. I felt like an idiot, trying my best not to stare, or stammer, but not sure I was succeeding. She had a stunning smile and (even though I was a virgin) had what I'm sure were cock sucking lips. I KNOW she knew I was staring, but she seemed to enjoy that. She wouldn't be flirting, her husband was a "Greek God" type guy, a masculine version of her. We talked for what seemed to be an hour, and I started working for them the next week. I STILL don't know why I was picked, when older, stronger, bigger guys had applied. BUT, you don't dismiss good fortune. They paid twice my usual rate, and extra if I stayed over on a project.
I looked forward every week to working for the doctor, more honestly, his wife, and after the second week, had me calling her Carly, and her husband, James. He wasn't home often, but was always just as nice as she was, when he did see me. As nice as he was, it was still intimidating standing next to him. He had to be at least six foot six, while I was the same height as his wife, five foot five. (When she wasn't wearing heels, which seemed to be only when she wasn't in the pool, or hot tub.) I felt guilty for oogling her, but couldn't stop myself. I was too shy, and too insecure about my height and slim body, that any dates I managed to get were "friend zone" dates. SO, my imagination, and internet porn, was my only release.
Every week, Carly would get me to sit and talk, after I finished the chores. She was very interested in me, for some reason. She finally got around to asking me about dating, and sympathized with my lack of success. She kept telling me that I would eventually find myself, then I'd start making relationships. I certainly hoped so. She was always so intense, like she could see right through to my soul. The week of my birthday, she called to wish me a happy eighteenth, an asked if I could come over Saturday, and Sunday. She said there were some projects, and she had a birthday present too. Nothing big, just something to show how much they appreciated me. My mom complained a little, but, since my birthday was Friday, we'd do the family thing that night. She knew how much I liked going to the Green's, and appreciated how it contributed to my college fund.
Friday came and I couldn't have been happier. With only a couple of weeks of school left, things were easy, just prepping for finals. I got to cut my last two classes, and made it home before my mom. She took me out for a birthday dinner, and gave me some gift cards, for clothes, etc, when I did start college. I didn't stay up late, because it sounded like I'd have a full day tomorrow.
Carly answered the door almost as soon as I rang the bell. Usually, she was in her many bikini's, but today, she was dressed to go out. A green dress that wrapped around her like it was sprayed on, and really high heels. As soon as the door closed, she hugged me so close, and pressed her lips on mine. FUCK! I've never been this close to anyone before. The kiss was short, but I could taste her lipstick. She smiled so big and whispered, "Happy Birthday, Andy! I hope it's your best one yet!" I stood there, stunned. Yes, I'd 'imagined' something like this, but my imagination could NOT compare to reality. She took my arm, led me out to the back yard, gave me a list of things to do, and told me she had some shopping to take care of, but would be back later. She said if I finished before she got back, to get in my trunks and relax in the pool. She left an iced pitcher of lemonade on the table. I felt like I still had the goofiest grin ever, on my face, but managed to nod.
Watching her walk away, like a runway model, I was in a fog. The few minutes before kept running through my head. It might have been nothing to her, but I'd gotten my first kiss, by a goddess. Yes. I knew she was married, and I didn't have a prayer, but, STILL, it HAPPENED. It was very hard to concentrate, but I managed. The lemonade was delicious, and I made several trips to get more, as I worked through the morning. Noon came and went, and I finally got in a rhythm. I finished about two-thirty, and popped into the pool house to change into my swim trunks. I had another glass of lemonade, and dove into the pool. I loved diving to the bottom, and sitting there until I needed to come up for air. When I did, my eyes got wide. She was standing by the edge of the pool, STILL in that dress, and heels. Could she not tell that as close as she was, I could see up that dress? STOCKINGS! She was wearing thigh high stockings, and I know, because I saw the skin above the tops. I forgot to close my mouth, and choked on a mouthful of water. I turned red, partly from choking, partly because of why. She seemed to ignore it, and said that she would be down in a few minutes.
I recovered, and swam a few laps, just to clear my head. Did she NOT know what she was doing to me? Is that possible? I was on my third lap, when I saw her beside me, diving in the deep end. She floated to the top, on her back. I'd never seen THAT bikini before, it was basically three tiny triangles, not quite covering up her most private parts. In the center of the top two, her nipples pushed through like pencils. I WANTED not to look, I did. But, I was mesmerized. She grinned and asked if I liked her new bikini, and I stammered out a yes. She reached out for my hand and asked me to join her in the hot tub. "You've never tried our hot tub, have you?" I gave up trying to clear my throat, and just shook my head.. As we walked closer, she said, "Oh, good! You've been enjoying the lemonade. I made it especially for you." She sat me on the edge of the hot tub, with my feet in it, and she sank down in the water. She popped back up, with a hand on each of my knees and asked, "Are you ready for your birthday present?" But, without waiting for an answer, she rose up, AGAIN pressed those full lips on mine. Her tongue pushed into my mouth, swirling on my tongue. My heart was pounding, and my cock, however small, was stiffer than it's ever been. I felt her hand slide down my chest, and snake into my trunks, pulling me free. She leaned back, licked her lips and said, again, Happy birthday, Andy." And kissed her way down, until I felt her lips on my cock. I was shaking so bad. I TRIED to say stop, we shouldn't, but nothing would come out.
Her eyes, bright and shining, were locked on mine as she licked, sucked and kissed. I thought I was going to have a heart attack, right here. WHY was she doing this, where was James, and PLEASE don't stop! I'm not sure, but I think I was cumming non-stop. She kept moaning and cupping my balls. We BOTH knew I wasn't going to last long, she was trying to suck the life out of me. My hips started jerking, and her eyes widened. I didn't understand HOW she could smile like that, with my cock between her lips. JUST before I blew what had to be the load of my life, she pushed a finger inside me.
"F-F-Fuuuccckkkk! Wh-WHAT are you doing???" Not that I expected an answer, I was filling her mouth with my cum. She kept licking, sucking, until she was sure there was nothing left, and rose again, pressing those cock sucking lips on mine. It never occurred to me what she was doing, until she pushed my cum into my mouth, and swirled it around my tongue. I tried to pull away, but her hand held my head. She was moaning, and pulled away. "Swallow, Baby. I promise, you'll like it."
I don't think I could have refused, no matter what she asked. I slumped, and she dropped back to my cock, which, weirdly, was still hard. She was licking, kissing, stroking. In a soft sexy voice, she whispered, "we weren't sure what to do for your birthday, but James suggested this. He always has the best ideas. Mmmm, you are ready to go again, I like that." and she again went to assaulting my cock, but immediately started easing a finger in me. I raised up a little, but her other hand pulled me back. It felt so weird, and dirty, but she was hitting something that went all through me.
"Ohhh, God. Why... are you.. d-doing that?" I got no answer, except another finger."Woooahhhh, FUCK... fuck... fuck..." My hips were twisting, in movement with her.. I was hoping this isn't gay, because it feels so good. I was cumming again... but... it wasn't stopping! I just kept spurting, and my hips kept jerking. Carly raised up, pushed me onto my back, and again put her lips on mine. This time, though, I opened mine. Her body was pressed tight against me as I accepted my cum. She wiggled on me then slid off me. I thought she was going to suck me again, but...
I felt her tongue... on my star. Surely she's not... OOOOOO, she is. Her velvet tongue pushed into me. WHAT a feeling. This is TOO kinky, but... WOW! I'm not sure how long she did that, but she sat up, whispered in my ear, "Here is your second gift, Andi." I felt her finger pressing against me, but her hips were right on me. Her finger... it's bigger. Then she moaned, and pushed. "Will you be my girl, Andi?"
WAIT, What?? it... it CAN'T be!!! She can't have.... HER cock was sliding deeper than her fingers... I wanted to yell, to toss her off me, but... it felt incredible... I wasn't thinking, my hands went to her hips... My cock was stiff again, rubbing on her stomach as she grinded on me I DIDN'T want her to do this, but I DIDN'T want her to stop. She reached behind to to untie her top, and rubbed those stunning breasts, with the pointed nipples, on me, as she kissed and fucked me. NEVER, in my wildest dreams, could I have imagined this, OR that I'd want this. But, here I am, moaning, "It's soo good! Fuck me Carly!
"Mmmm, yes, baby, we knew we had the right girl for the job! Let's go upstairs and make you pretty, ok?" My mind was spinning, WHAT? Make me pretty? She slid out of me, and I think I groaned. I wasn't gay, but, She wasn't a guy, and... it felt amazing. I was so close to cumming for the third time in under 15 minutes (I think, time was all messed up.) She hugged me as we walked into the house, and up the stairs, her boobs bouncing carelessly, nipples pointing straight out. At THAT point? She could have asked me ANYTHING.
She pushed me into a massive master bath, and sat me on the toilet. She knelt in front of me, with a pink bottle, and started rubbing lotion on my legs and on my crotch. Like I wasn't hard enough, my small cock STILL felt like it was leaking. Her smile never dropped, as she winked at me. "We are going to have SO much fun! I'm so excited that you are spending the weekend with us. It was SO hard to wait until you reached eighteen, baby." She saw me staring at her cock, which wasn't any bigger than mine, but certainly didn't belong on that body. "Oh, I surprised you, huh? We thought it might, but you'll see, you're just like I was, at your age."
I must have been in some kind of fog, I didn't understand how we could be the same, at all. After a few minutes, she stood, pulled me up, and pulled me into the shower. We both stood under the hot water, hugging, those perfect boobs mashing into me. She was kissing me, and with a hand spray nozzle, was rinsing the lotion off me. She shampooed and conditioned my hair and rubbed me down, EVERYWHERE, with body lotion. I felt SOOOO smooth. We got out of the shower, and dried off with the softest towels I'd ever felt. She sat me at her makeup table, reached over, pulled a pill out of a small bottle, and popped it in my mouth. "You'll like this. Now, close your eyes, and let me work on you."
I just nodded. I was so hyper-sexed, and mellow-spacey, I didn't care what she did. I felt her rubbing something cool on my chest, and then press something on. I opened my eyes, but she told me not to peek yet, so I didn't. I WANTED to, because I felt 'heavy'. Then I felt her brushing my face, as she hummed. She whispered, "You are so pretty, Andi, James is going to LOVE you, just like I do." My mouth dropped open. James would? That seemed weird to me, but she just kept working. I felt her doing something with my hair, curling, I think, and then the hair dryer. "Don't jump, this will sting a little, ok?"
"OW! What the.." My ear stung like crazy.
"It's alright, just one more. We are almost done." She used her fingers to softly drop my eyelids, and I felt the sting in my other ear. Damn, THAT hurt. She pierced my ears? "There, now one last thing, and we can get dressed!" She led me back into the bathroom, stood me in front of the toilet, making sure to keep my eyes away from the mirrors. She reached be hind me, and caressed (I thought) my bottom, until I felt something push in me. "Sit down baby, we need to clean you out, for our big birthday night." I did, and felt a rush of something warm flow inside me. " Now, push it out, and we'll do it one more time." It felt strange, but kind of good. It made me feel tingly inside.
She again stood me up, wiped me, and walked me into the bedroom. There was the biggest bed I'd ever seen. On it was laid out two women's outfits. "uhh... i-is one of those... f-for me?"
"Well, yes, baby. Don't you want to be our girl? Come on, let's get you dressed, you'll love it, I PROMISE." She slipped a sheer bra over the breasts I just fully realized she'd put on me, then sat me on the bed, and pulled up matching V shaped panties up my legs. I shivered as I felt the material on my smooth legs. My legs! They... looked like HERS!
Then she pulled one leg out and slid a stocking up OH MY GOD. Then the other. She smiled, looking at my face. The first time is amazing, isn't it? Not another feeling exactly like it. She reached under the bed, pulled out a pair of high heels that looked like some I'd seen her wear, and she slipped them on my feet, and buckled the ankle straps. "Stand up slow, baby, get your balance" She held onto me until she was sure I was ok.
With that, she reached over, grabbed one of the little black dresses, and pulled it over my head, down my body. She smoothed it out. Took my arm, and walked me over to the full length mirror. See, Andi? This is the girl we hired." My eyes went wide, my mouth dropped. I looked... BEAUTIFUL. I DID look like her, if she were my age. My boobs weren't as big, but, I looked ALL girl. I couldn't stop staring. She was grinning as she got dressed, We could be mother/daughter. Well, THIS is.... confusing. I'd lusted for her for months, she sucked my cocked, THEN fucked me, and, now... THIS? Weird. I wanted to fuck myself. WAIT... other guys... would... too. JAMES! She said James would love me... But... but..
I turned to her, and she could read my face. "Yes, baby, it's confusing, and all new, but, we knew as soon as we met you, who you were meant to be. You will love your new life as much as I did, when I was your age. Come on, let's go downstairs, have a drink, and wait for James to get home. You'll need to practice walking in your heels, anyway. AND, that gummy should be kicking in soon."
She was not kidding, by the time we got down the stairs, it was creeping on me. Such a warm glow, and every time I looked down at myself, I got all tingly inside. She made us each a drink, and hugged me as we drank them. "I hope he gets home soon, baby, I want to kiss you all over, but don't want to mess up our makeup. We want to look sexy for him, don't we?" I nodded, but wasn't really sure. Yes, She felt really good inside me, but James? He was huge. I never stared, but it was obvious there was a snake in his swim trunks. I'd NEVER once thought about guys... sexually. What would it be like, being a girl... to a man?
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