Start of the Summer Ch. 02

A little history

I started experimenting with cross-dressing in high school. When I had the house to myself I would try on my sister's things and once I figured out what fit I sometimes wore panties under my jeans, a bra under my sweatshirt, a garter belt, anything. I was always incredibly careful about when and where I did it, though. Before the incident with Brad I got caught only once.

It was the summer after I graduated high school, right before I turned 19. It was exactly two years before the thing with Brad that I told you about in Chapter 1. I was house sitting for Mr. & Mrs. Walker down the street while they were on vacation. I fed the cat, watered the plants, mowed the grass, picked up the mail and cleaned the pool. They paid me pretty well, plus there was a huge, secret bonus -- as soon as they left I made a beeline for Mrs. Walker's closet. I was pretty sure I'd fit into her clothes and I was right. From there on I had a full-time cross-dressing party. Every day I'd dress up in a different outfit - skirts, dresses, lingerie. I'd wear her yoga outfits and jewelry -- anything I could get my hands on. I watched youtube videos and learned how to do makeup. I shaved my legs, chest and armpits and wore a skimpy bikini outside when I cleaned the pool, but I was careful not to stay out too long because I didn't want to get tanlines that could give me away. I must have jerked off ten times a day. It was heaven.

Anyway, all good things have to come to an end, and my fun ended abruptly when the Walkers came home a day early and found me dressed in Mrs. Walker's lace teddy, wearing red lipstick and nail polish, jerking off into a dishtowel on their bed. I had no idea how long they were standing in the doorway watching me as I lay back with my eyes closed, but after I grunted and groaned my way to an orgasm and opened my eyes, there they were staring at me in fascination. Mr. Walker was pointing his cell phone at me, taking video.

I was so ashamed. I didn't know what to do so I just lay back and closed my eyes. I felt my cheeks turn blazing red. Tears started streaming down my face.

The next thing I knew Mrs. Walker was making me sit up, wrapping her arm around my shoulders and comforting me. I was just crying and babbling excuses -- I thought my life was over -- but to my surprise Mrs. Walker just started rubbing my thigh and whispering in my ear, telling me not to be scared, not to worry, and that I made a really cute girl.

Still whimpering, with my nose running, I looked at her in utter surprise.

"Really," she exclaimed, "you look sexy in this teddy. It's one of my favorites -- you have good taste, baby!"

She was rubbing my back and I started to calm down, and that's when she got more explicit. She told me how sexy my red lips were, and how good the lace teddy fit my smooth body. She rubbed higher on my leg and told me I was a hot little bitch, and how any guy would get all worked up if he could see me all dressed up.

I couldn't believe it when Mrs. Walker slid her hand up into my lap, under my panties and started jerking me off as she whispered nasty things in my ear. My cock was back to being rock-hard in seconds and she had me coming in no time.

For the rest of the day Mrs. Walker dressed me up like I was a doll, making me try on different things, pose for her, doing my makeup, playing with my hair, putting bracelets and necklaces on me, painting my nails.

I loved it more than anything. She dressed me up in a skirt and made me jerk off in front of the mirror. She put lipstick on me and made me suck on her tits while I jerked off and came all over her leg. She fitted me with a long blonde wig, put on eye shadow and makeup and taught me how to rub her clit until she came. It was the best afternoon I ever had! I came again and again.

I only had one worry going through my mind, and eventually I got up the courage to ask her. "Ummm . . .," I stammered.

"Yes?" she replied, "what is it sweetie?"

"Ummm . . . uh . . . . um, what about that video Mr. Walker took?"

She looked at me sternly, like I was speaking out of turn. "What about it?" she responded coldly.

"Uh . . . you're not going to show it to anyone, are you?" I asked nervously.

"Don't worry baby," she said in a comforting tone, "we're just going to keep it for -- let's say -- insurance."

"Insurance?"

"Yes, sweetie, to insure that you do exactly as we say, OK?" She looked at me thoughtfully. "You see, dear, we're going to have you do things you may not think you want to do, but deep down you really do. So, since we have the video, you'll pretty much have to do whatever we say. You see?"

I nodded dumbly. This didn't sound very comforting to me.

"This way," she continued, "you don't really have to think about things too much, OK? You won't have any inner conflicts, so to speak. You'll just have to do as we say. And you'll like it . . . you'll love it . . ."

She smiled with encouragement, as if she was talking to a puppy. I kind of understood what she was saying, but I wasn't sure what kind of "things" she was talking about. She watched me pondering the situation.

"Don't worry, baby," she said soothingly. "We'll never make you do anything you don't really want to do . . ."

* * * * *

After our afternoon of dressing and playing Mrs. Walker made me shower with her and shaved me smooth, then dabbed me with powder and perfume after drying me off.

"I think from now on we're going to call you 'Katie,'" she informed me. "Yes -- Katie."

"Katie?" I thought. My name was Ken. I started to protest, but she quickly shushed me.

"Katie!" she said with finality "If you want to dress like a girl, you need a girlie name. You're Katie now, understand sweetie?"

I nodded submissively. It kind of made sense, I realized. Actually, it made a lot of sense, and Katie was a cute name, I thought to myself. Yes, Katie . . .

We smiled silently at each other, a quiet understanding passing between us.

"OK, then," she purred, "now it's time for the main event . . ." She dressed me in pink panties and a matching bra, then added some silicon breast forms to give me perky b-cup tits. They even had hard nipples poking out. She make me slither into her faded Daisy Duke cutoff shorts that were incredibly tight, then added a little red halter top that showed my belly button. She did my makeup, with bright red lipstick to go with my red nail polish. She put a wig on me, giving me shoulder-length strawberry blonde hair that she tied back.

I looked in the mirror and saw a hot, young, slightly trashy girl looking back at me. I looked great and felt really sexy in a way that I never did before.

Next she lit a joint and made me take a few hits. It was really good weed and I had a great buzz going. She whispered in my ear, "just follow my lead -- everything is going to be wonderful."

Things got a little hazy but the next thing I knew we were out back by the pool. Mr. Walker was lounging on a chair in a black speedo and Mrs. Walker was standing behind him, rubbing his shoulders. He was ripped, with broad shoulders and six-pack abs, and black hair all over his chest and legs. I noticed for the first time that he had penetrating dark brown eyes framed in his chiseled face, with a few days of stubble in his beard. He looked like the essence of manliness.

Standing there in short shorts and a halter, with my hard nipples poking out and my makeup and nails done, I felt incredibly vulnerable and submissive. Fortunately Mrs. Walker was there to tell me what to do..

"Come here, baby," she cooed. "Come help me rub his shoulders." She directed me to stand in front of him and squirted some lotion into my hand. "You do his front while I do the back," she commanded. "We don't want him to burn, do we?" she giggled. "We girls have to take care of our man . . ."

Mr. Walker looked up at me with those dark eyes and I shivered. He leaned back a little to give me room to rub, and my hands instinctively went to his strong shoulders, spreading the slick lotion over his skin. His firm body felt good under my hands and I could feel his eyes roaming over me.

"That's good, honey," Mrs. Walker said encouragingly, taking my hand and squirting more lotion in it. "Now do his chest." Mr. Walker leaned back even more as my painted fingers roamed over him, spreading the lotion across his sculpted chest. Mrs. Walker came around and stood next to me, rubbing my back softly as I oiled up her husband.

Mr. Walker was lying back now, a big smile on his face. "You've got good hands, sweetie," he said in his husky voice. His praise made me feel so sexy and sent a warm feeling through me. I felt so feminine and so natural -- all I wanted to do was please them both.

Mrs. Walker was rubbing my neck now, whispering in my ear. "You make a really sexy girl, honey . . . you like rubbing him don't you? . . . you like having your dainty little hands all over a big, strong man, don't you?"

I just nodded, feeling her softly massaging my neck while my hands roamed over his muscled pecs and abdomen.

"Do his legs now," she whispered, applying gently pressure to my shoulders, urging me downward. I dropped my gaze and saw a huge bulge in Mr. Walker's speedo. My mind was still a little fuzzy from the weed, but suddenly I realized where this might be going and it made me swoon. "Do his thighs," she demanded, pushing a little harder now. "Get on your knees baby."

For a moment I was conflicted, but then I looked into Mr. Walker's dark eyes, to the hard nipples poking out from my pink top, and to the red nail polish on my fingers as they slid through Mr. Walker's chest hair.

I just had to do it. I couldn't not do it. I dropped to my knees and held out my hand for another squirt of lotion.

"Good girl," Mrs. Walker purred as she squeezed out a dollop of goo for me.

Mr. Walker spread his legs, giving me a perfect view of the hard shaft encased in tight black nylon. It looked powerful and mysterious -- I'd never seen any man's hard cock, let alone a huge one right in front of my face, on my knees dressed as a sexy tramp.

Mrs. Walker was still rubbing my back now, whispering encouragement. "Yes, rub his legs . . . make sure to get every inch of his thighs . . . not just the tops . . . that's it, spread his legs more and get aaaaaall the way in there . . ."

Mrs. Walker was rubbing my back and I was on autopilot, following her directions diligently, rubbing the lotion over the insides of Mr. Walker's thighs, from his knees all the way up to the band of the speedo, my eyes fixed on the giant cock throbbing just a few inches in front of my face.

As my slippery hands wandered along his skin Mrs. Walker reached over my shoulder grasped the waistband of his suit. He raised his butt as she slid the black nylon down his legs, exposing his raging member to me. I just stared at it, unable to move.

It was the first big, hard cock I'd ever seen, and it seemed gigantic, more than twice the size of my little thing and throbbing with powerful, masculine energy. It had sinuous veins pulsing along its length and curved upward to a flared, smooth mushroom head. It seemed like a weapon.

My eyes wide, I finally looked up at Mr. Walker as he fixed me with those dark, penetrating eyes, a huge grin spreading over his face.

Mrs. Walker kneeled down next to me and wrapped her hands around his pole and started pumping, her oily fists sliding up and down his length.

Turning to me, she whispered, "this is what all us sexy girls want, don't we?" she asked. I started to speak but she brought her lips to mine, slipping her tongue in my mouth. I returned her kiss eagerly and we kneeled next to each other making out while she jerked her husband's shaft in the bright sunshine.

As we kissed she reached down to take my right hand in hers, then lifted it back onto her husband's thigh. I felt like I was in a dream. I was nervous and excited, and when she placed my hand on his big, hard shaft my fingers instinctively curled around it and started pumping.

I marveled as I looked at my fingers, slippery with tanning oil, my nails painted bright red, wrapped around Mr. Walker's throbbing cock, stroking him from base to tip. I was amazed at the power of his pulsing member in my hand, fleshy yet hard as steel, throbbing with heat.

Mrs. Walker was rubbing my shoulders again, encouraging me. "That's it baby, jerk him off . . . stroke that big cock . . . yes, baby, you're a natural . . ."

I was lost in the moment, holding my first cock, when again I felt a subtle pressure on my neck. Mrs. Walker whispered in my ear, "kiss it!"

My heart was pounding as I stared at Mr. Walker's powerful tool. "Kiss it!" she urged, pressing me forward. "You want to know what it feels like to be a girl, don't you? . . . . you know you do . . . . kiss it!" she hissed in my ear, "kiss it . . ."

I looked up at his sculpted chest, his broad shoulders, then back to his big cock and an incredible hunger welled up in me. I leaned forward and planted a soft kiss on the big, mushroom shaped head. It felt soooo smooth against my lips. I kissed it again and looked to Mrs. Walker who was nodding with approval. "Yes," she urged, "that's it . . . kiss it . . . lick it . . . "

Mr. Walker was smiling down at me as I kissed his throbbing member all over, then started licking it from top to bottom. I couldn't get enough. Licking, kissing, fisting -- I was totally engrossed on the hard, pulsing tube of flesh when I felt Mrs. Walker grab my chin and guide my mouth to the head of his stiff pole. "OK, baby, that's enough licking and kissing for now . . . it's time for you to learn to suck cock for real . . . "

I looked to the hard, dripping cock in front of my face and then to Mrs. Walker who silently mouthed the word "open" to me. When I obediently parted my red lips she smiled and pushed my head down, sliding her husband's fat, oily cock into my virgin mouth.

"That's good baby," she purred, guiding my head down, "suck on it . . . learn to be a good little cocksucker, baby . . ."

I let the knob push open my lips and penetrate my mouth. Soon, the whole head was past my lips. I closed my eyes and trembled as I felt his hard cock invade my mouth, sliding over my lips and tongue. Yes, this is what I was now, a sexy, slutty tramp, on my knees, sucking another man's cock, dressed in short shorts and a halter top. And I loved it!

I wasn't sure what to do, but Mrs. Walker was guiding my head up and down and whispering encouragement to me. "Yes, baby, keep your lips wrapped around him . . . that's it . . . use your tongue . . . " she purred.

I twirled my tongue around the head of his cock, causing him to moan. As my tongue explored his knob, my right hand slowly started rocking back and forth, fisting the base .

"That's good baby," she said. She took my other hand and brought it to his balls. "Start rubbing now . . . be gentle . . ."

I caressed his balls as Mrs. Walker guided my head up and down, slowly advancing my mouth to take more of his cock on each stroke. Just a bit at a time. Advance a bit, go back to the head. Flick my tongue all over. Keep my lips tight. Push back down, then pull back again. Try to relax. Tongue. Lips. I was getting into a steady motion.

I was following Mrs. Walker's directions slavishly, which made me even more hot. I loved giving up control, being dominated, being used. Following her commands, I was soon bobbing my head up and down on his cock with ease, holding the base in my fist and massaging his balls at the same time. It felt great. The warmth of the cock in my mouth. The sheer size of it stretching my jaw. The pleasure I got from thinking that I was a hot, sexy girl pleasing my man.

Mr. Walker's moans were filling my ears, letting me know I was doing a good job. When he started pushing his hips up off the chair I realized that he was going to come soon. I was scared for a second, but Mrs. Walker seemed to know exactly what I was thinking and whispered in my ear, "Yes, he's almost there, baby . . . and you're going to swallow every drop . . . you're a natural cocksucker, baby, and you're going to love swallowing come . . . hot come . . . you're going to love it, baby . . ."

A chill went through me and I knew deep down she was right. Immediately I had an incredible yearning to swallow his come which made me suck and stroke him even harder.

"That's it baby," Mrs. Walker praised as she saw me increase my pace, "suck him off . . . jerk him off . . . make him come . . ."

I was eagerly bobbing my head, my right hand following my mouth with each stroke, my left hand working his furry balls. Mr. Walker's moans were getting louder, and I could feel his rod get even harder and even swell a bit more. This is it, I thought. He's about to blow. . .

Suddenly his face changed and his moans got louder. I felt his legs tense up. His balls tightened and then I felt it in my fist -- the come rising through his shaft like a fire hose. I'll never forget that first blast of come into my mouth. Mr. Walker's grunts and groans filled my ears as the head of his cock swelled up and then shot a hot, thick stream of semen into my mouth. I stopped my bobbing and stayed still, fisting his shaft and holding the squirting head of his cock on my tongue, my lips pursed tightly around him as he delivered spurt after spurt of warm, salty come into my mouth. I looked up at him as he emptied his balls into me, grateful to finally experience the fantasy that had been simmering in the back of my mind for years. Our eyes were locked together as he shot out three, four then five bursts of fluid into my mouth. I moaned in delight. I loved having my mouth filled with come. I loved the taste. And when I finally closed my eyes and swallowed deeply, shivers ran through me at the wonderful feeling of warm come sliding down my throat to my stomach.

"Wow!" exclaimed Mrs. Walker, a proud grin on her face, "you are a natural! Now do you believe we wouldn't make you do anything you don't really want to do?"

* * * * *

After I blew Mr. Walker and swallowed my first load of come, Mrs. Walker took me into the poolhouse and fixed up my makeup and lipstick, brushed my hair and adjusted my breasts. When she decided everything was just right, she looked at me with a grin and said, "OK, sweetie, now it's time for your next lesson."

She brought me back outside and took a seat next to Mr. Walker who was still lounging naked on his chair, having a snooze. Mrs. Walker shimmied her bikini bottoms down and off, then spread her legs wide. "Come here, baby," she beckoned, pointing to the ground in front of her. "Get back down on your knees -- time for you to learn how to eat pussy."

This was another first for me, but immediately I was overwhelmed with a hunger I'd never known before. Her pussy was beautiful -- clean shaven and shining in the sun, a perfect slit framed by pouty, fleshy lips that I couldn't wait to suck on. I kneeled down and looked up at her, not sure what to do.

"Honey, would you give him a little lesson?" she asked, turning to Mr. Walker and poking him in the side. He roused from his nap, a big smile spreading across his face when he saw me on my knees between his wife's wide-open legs. He rolled down next to me and for the next twenty minutes he taught me the art of pussy eating. He showed me how to nibble on her lips, lick up and down her slit, slide one and then two fingers deep into her cunt, and how to kiss and tease all around her clit. Together we brought her to a crashing orgasm, then he grabbed my head and gave me a deep, wet, soul kiss, our tongues churning together in a haze of pussy juice while Mrs. Walker caught her breath. His beard was rough against the soft, smooth skin of my face, making me feel even more like a sweet little girl.