Courting Cheryl

Steering up the long winding driveway I had a feeling of apprehension. Leaving everything I've known my entire life and traveling half way across the country was more than just a little out of character for me, it was borderline insane.

Up until a few weeks ago I was working in a managerial position for what I thought had been a stable successful manufacturing company, I had been there for fifteen years. Then charges of embezzlement and "cooking the books" and the next thing I know the company is out of business and I'm out of a job. I guess I was ready for a change in my life.

I had first met Cheryl in an interracial chat room over a year ago, and we hit it right off, which you might think is ironic since we're both white but there are plenty of guys like myself who think there is nothing more erotic than the sight of a hot white chick getting it on with a black guy.

I've never been married but I've had my share of girlfriends in my forty-five years. Yet there was no one that I felt comfortable enough with to open myself up to totally. I've always been kind of shy and awkward around beautiful women. I have much more confidence talking online. I bared my soul to Cheryl, telling her all my kinkiest cuckold fantasies and she befriended me all the more.

Not that I'm a total submissive, I can be as dominant as the next guy, sort of, but my hottest fantasies always involved me exploring my sub side, and due to the nature of the chat room, that was the side Cheryl and I mostly discussed.

Cheryl is twenty-eight years old with blue eyes and honey blonde hair. She had made a small fortune in a very successful modeling career and had more recently discovered that she had a real talent for writing. After having several short stories published in magazines, she had sold her first novel to a publisher about 8 months ago, which was about to hit the bookstands any day now. The publisher gave her a hefty advance for a second novel, upon which she was now furiously working.

During our conversations she had mentioned several times that when she writes she becomes so focused that she tends to neglect everything else. She said that what she really needed was a housekeeper but that she didn't feel comfortable having a stranger in the house. After my job fell through, she mentioned jokingly that I should come out to California, where she had just moved, and take care of her house.

I knew she was only joking but I started to seriously consider making the move. I had nothing holding me in Ohio anymore and while Cheryl had never expressed the least bit romantic interest in me, sharing a home with this luscious creature was a tremendous opportunity to get something started. So, throwing caution to the wind, I offered my services to her and she eventually accepted.

"Hey there Ron, it's great to finally meet you in the flesh." Cheryl said, hugging me as I stepped into her home. Her firm full breasts pressed into me as I returned her hug. She was wearing a loose t-shirt and short sweatpants, which I was soon to discover was her garb of choice to run around the house in. Even in these simple clothes and with no make-up or jewelry on, she looked absolutely beautiful.

"Great to meet you also." Now why did I say that? I was searching for something witty or funny to say but nothing came to mind. After all our intimate online conversations, I was terribly nervous standing here in front of her.

"Let me help you with this." She said as she reached to pick up one of my bags. No bra, I noticed as she bent down. She then led me to my room as I admired her shapely bottom wondering what kind of panties she wore. "This will be your room," she said, stepping into a room and setting the bag down at the foot of a double bed. "My room is the next door down, why don't set your stuff down and I'll show you around, you can unpack later."

She proceeded to show me around the large house. It was starting to become cluttered with clothes strewn around and dishes piling up in the sink. "You'll be in charge of cleaning, cooking and laundry." I nodded while imagining handling her dirty underwear.

Cheryl started asking me about my flight as she sat down on the couch, tucking one leg under her. I fought to keep my eyes on hers and not look between her legs as we made small talk. "I'd love to sit and talk all afternoon," she said eventually, "But I really do need to get back to my writing. Just get yourself settled and take a nap if you need to, I'm sure you're tired after your trip."

I headed for my room as she made her way to her den. I put my stuff away and tried to catch a nap but the combination of an unfamiliar bed and all the excitement of being in the same house with this gorgeous woman thwarted my attempt. I thought about jerking off but decided against it. Instead I decided to straighten up the living room and then get dinner started, all the while trying to figure out how I could get Cheryl to become attracted to me.

I prepared Chicken and rice along with some canned mixed vegetables and set two places at the dining table. I was hoping for some more conversation but I was disappointed when Cheryl asked me to just bring her plate to the den and set it on her desk. She was hammering away at her keyboard and barely noticed me as I left her meal. When I went to retrieve her plate an hour later I saw that she was still typing away and had not even touched her meal. "I'm sorry," she said, can you just wrap it up and leave it in the fridge? I'll eat it later."

Around 10pm she finally came staggering out of her den. "OK, enough for tonight, I can't see straight anymore," she said, "why don't you pick out a movie and I'll make some popcorn, the stack on the right side of the shelf is the stuff I haven't watched yet."

I shuffled through the stack and found a large variety of the latest movies to come out on DVD as well as several interracial porn discs. Should I pop one of these in? I though. It might seem very forward but we had sent each other plenty of interracial porn online. What I didn't want to do was to get into the "friendzone". I wanted her to think of me as a lover, not a housemate. So I held my breath and loaded "Black Boned" into the player.

When Cheryl returned with the popcorn and a couple beers, the image of a bikini-clad blonde hitchhiker being picked up by a black motorist with bulging muscles, was flashing across her 40-inch plasma TV. "You dirty old man!" she protested with a smile as she sat next to me on the couch. The scene suddenly switched to a bedroom, you have to love porn, and the black man was removing the blonde's top, exposing her huge breasts and she dropped to her knees and started unzipping his pants.

I began wondering about the wisdom of my strategy as the blonde hauled out a huge black cock out of the guys' pants and started sucking it. It must have been ten inches and as big around as my forearm. I was barely five inches on a good day. How could I measure up against a stud like this? Well, to late now.

As the stud soon spread the blondes' legs and started pounding her, I stole a glance at Cheryl's breasts to see her nipples had hardened. I cautiously slipped my hand into my pants to readjust my stiffening cock, hoping she wouldn't notice. The couple went at it in a variety of positions until the he signaled his partner and she scampered to her knees and tilted her head back, sticking out her tongue as he stroked his cock until he shot several spurts of semen into her mouth. The blonde then faced the camera and opened her mouth to show her cum covered tongue before swallowing it down.

"I bet you'd enjoy that Ron." Cheryl said turning to me.

I had never really talked to Cheryl about cumming in a girl's mouth and having her eat my spunk but I figured that she probably knew that just about all men are turned on by this act. I certainly was, I owned some videos that were nothing but I series of facial cum shots. I loved watching a pretty girl getting a load of cum shot on her face, in her eyes, on her hair and into her mouth. "Sure," I replied enthusiastically, "I think it's hot."

"Want to do it?" she asked.

I was dumbfounded; I couldn't believe my good luck. Screw smooth moves and come-on lines, all you need is porn! "I'd love to." I told her.

"Sweet! This is going to be so hot. Lower your pants and lie down on the couch, I'll be right back!"

She scampered out of the room as I tried to figure out what was going on. I concluded that she was going to position her face over my stomach as I jerked off into her mouth. I was kind of disappointed that I wouldn't be able to get as good a view as if I was standing and she was kneeling in front of me, but oh well, if this is the way she wants it, I could deal with it. The thing that had me more concerned was exposing my undersized member. I decided the best course was to get it as large as possible before she returned, so I slipped down my pants and started stroking.

"Hey big boy, wait for me." She said returning to the room and kneeling down on the floor next to me. If she was disappointed by my size she didn't show it. Her eyes shined as she watched me and she slipped a hand into her sweat shorts and began stroking herself. "Let me know when you're about to cum."

I fixed my eyes on her hardened nipples poking through her t-shirt and quickly approached the point of no return. My orgasm was seconds away when I gave Cheryl the signal, but instead of moving her face in front of my cock, she produced a small glass and held it in place as I erupted and shot my cum into it. "OK," she said, "open wide." As she brought the glass over my mouth and started tipping it. This wasn't going right at all. Seeing no way out, I opened my mouth and she poured the contents of the glass in. "Hold it in your mouth and wait for me." She said as she stroked herself faster. She watched my face intently as I held the warm salty liquid in my mouth. Soon her breathing was getting more rapid and her face began to contort in an expression of pure lust. "Swallow!" she yelled as her body began to shudder. I gulped and my cum started sliding down my throat. "Mmmmm." She moaned.

"Whew, that was hot." Cheryl smiled as her breathing began returning to normal. "You are so cool." She gave me a kiss on the cheek and then got up and made her way to the bathroom.

The next few days were fairly uneventful. Cheryl spent most of her time at her computer working away. She usually ate her meals there and sometimes fell asleep right on top of her keyboard. I took one of these occasions to go through Cheryl's closet. She had a number of erotic outfits including a 4 appendage tie up kit, with blindfold and nippleless and crotchless panty set. "Pretty hot, huh?" Cheryl said startling me. I blushed and said it was wild.

"I have an outfit that you will absolutely adore." She said, brushing past me and moving deeper into the closet. She produced a black French Maid outfit that had frilly white lace trimming, black fishnet stockings and thong panties. "Like it?" she asked, holding it up.

"I love it."

"I knew you would," she said excitedly, giving me a big smile, "put it on and then come out and do the dusting." She then turned and bounced out of the room.

Once again I was dismayed by our, or should I say my lack of communication. I did recall telling Cheryl once that I had tried dressing up in girls clothes and thinking that it was kind of hot, but this was not what I had intended at all. I began disrobing and putting the outfit on. Everything was made of stretchy material, obviously intended for a variety of body shapes, but it was still very small on me. The short skirt left half of my butt exposed. I felt very silly as I crept into the living room.

"Woohoo," Cheryl yelped giving me a wolf whistle from where she was sitting on the couch. "Yeah baby, you're a hottie!" I blushed again as I picked up a feather duster and began working so I wasn't just standing there looking ridicules. As I was dusting a windowsill she came up behind me and fondled my butt before giving it a quick pinch. "Nice buns baby." She said. I must admit that I did like the attention. Over the next hour She was practically all over me as I did my work.

The phone rang and Cheryl went to her room and began talking to what must have been one of her girlfriends. I strained to overhear the conversation. At one point they started talking about men. "Take Lance Armstrong for instance," she was saying, "he rides a bicycle, a freaking bicycle. Yet he puts his entire being into riding that thing and it takes on greatness. I think that is so hot, I would totally do him."

That was it! I thought. Cheryl was turned on by people who totally dedicated themselves to something. That's the key to her heart. But what could I do? I certainly was no athlete. I didn't have any artistic or musical talent. What could I excel at? What could I dedicate myself to in order to win Cheryl's affections? I was deep in thought dusting a mirror when it hit me. In fact it was staring right at me. That's it! I almost shouted out loud. Cheryl had just been all over me just because I was wearing the maids' outfit. Dressing in women's clothing was the key. I was going to become the Lance Armstrong of cross dressers!

The next day I went shopping. I had never shopped for women's clothing before and I was quite lost while wandering the aisles of the department store. I got quite a few stares and giggles from the sales girls as I held articles of clothing up to me to try to determine their fit. I had no clue about sizes. I chose a couple skirts and blouses that seemed to go together well and then debated about buying shoes and underwear.

I decided I could always wear the panties from the French Maid outfit but I figured Cheryl would be disappointed if I didn't have a nice pair of heels. So screwing up my courage I headed for the shoe department.

I was searching the racks for something that would fit when a high clear voice from behind me said, "Hi, I'm Jen, can I help you?"

"Ummm, yes, well," I stammered, avoiding eye contact with the trim young girl "I'm looking for something in a size 10."

"The men's shoes are on the other side."

Ummm, yeah, I know, I-I was looking for something with like a three inch heel." I said, feeling my face redden.

A knowing expression crossed her face, she asked me to sit down while she measured my foot. She then went and brought back several pairs of shoes. "See how these fit." She slipped a pair of black strappy shoes on my feet and I tried to stand up. "New to this, huh?" She said as I wobbled and grabbed her shoulder to keep my balance.

"Yes, very." I replied. The shoes were uncomfortable but I guessed that was just because I wasn't used to wearing heels. "I'll take them." I said after taking a few tentative steps, wanting to get out of this situation as fast as possible.

"I think these are on sale. Linda," She suddenly called out, "are these on sale?"

Another girl came over and stifled a giggle as she saw me standing there. "No," she said, "You know that brand never goes on sale."

"Oh yeah," Jen said with a mischievous grin on her face, "sorry, I forgot."

Returning home I quickly prepared lunch for Cheryl and then went into my room to change into one of my new outfits before serving her.

"Oooo Sexy!" she said as I stumbled into her den. "Let's see you walk back and forth."

I set the tray with her lunch on the desk and then carefully walked toward then door, tuned and then back towards her.

"You walk like a man," she frowned, "Put one foot more in front of the other as you walk, this will give you a sexy wiggle rather than shuffling along the way you do." I gave it a try almost losing my balance a couple times. "That's better, you just need some practice. Where did you get these clothes?"

"I went shopping and bought a couple outfits."

"Oooo, show me what else you got."

I hurried to my room and changed into the other outfit. Cheryl was sitting on the couch when I emerged.

"Nice!" she said, admiring the clothing, "anything else?"

I told her that this was all I had purchased. She said she would take me shopping soon for more clothes. "What you really need is a little make-up." I followed her to her room and she sat me down at her vanity. She proceeded to apply mascara, eyeliner, eye shadow, and some red lipstick to my face.

The change was fairly dramatic. "We'll need to get you a wig until your hair grows out." This was working better than I had ever imagined, Cheryl was practically fawning over me. I was quite pleased with myself for coming up with this clever ruse.

"I'd love to stay and play but I really do need to get back to work." She said. She then gave me a pat on my butt and a kiss on the cheek before returning to her den.

Over the next few days we went out shopping together several times. Cheryl helped me pick out a nice brunette wig with long spiral curls, several new skirts and blouses, a couple more pairs of shoes and about a dozen pairs of panties. She also helped me select my own assortment of make-up. While shopping she always made sure the salesgirls knew these items were for me. I didn't mind, I was just happy that Cheryl and I were spending more time together.

"Why don't you throw away all those icky male clothes?" Cheryl asked me one day as I was putting some of my new clothes away after one of our shopping sprees.

"What about when I go out?"

"You only go department store and grocery shopping, that's no big deal and you look totally hot dressed as a girl, no one will know."

I looked at the expectant expression on her face and knew there was no way I could refuse her. "OK, let's get rid of it." We packed up every article of male clothing, shoes and all and took them to the Goodwill. Being out in public for the first time wearing women's clothing was a bit nerve-wracking, but having Cheryl with me gave me confidence. Walking in heels was now becoming second nature to me and Cheryl often complimented me on the wiggle in my walk, playfully patting my butt.

Cheryl took advantage of the first warm sunny spring day in northern California to do a little sunbathing on her deck. The house was nestled in a large wooded lot providing total seclusion. I was washing the dishes from lunch when I heard her call out asking for a glass of iced tea. I filled a glass with ice, poured the tea in it, added a wedge of lemon and inserted a straw, just the way she liked it before taking her drink out to her. Stepping out on the deck I saw that Cheryl had removed her bikini and was laying on her stomach on a chaise lounge. I handed her the glass and she took a long sip before setting it down on a table and laying her head back down. I couldn't see through her dark sunglasses but I assumed her eyes were closed, so I took a few more moments to admire the lusciously curved loaves of her ass.

"Like my butt?" she asked.

"Oh, sorry, ummm, yes, it's lovely." I stammered.

Taking off her sunglasses she looked me square in the face. "Wanna kiss it?"

I fidgeted and blushed but no words came to me.

"Go ahead, you know you want to." She said, arching her back and lifting her rear a bit.

Kneeling down at the end of the lounge I brought my lips to the warm flesh of her sexy bottom. Cheryl spread her legs and lifted her butt a little more indicating that she wanted more. I began placing soft kissed on her ass moving closer and closer to her asshole. I extended my tongue and lightly traced a trail up the crack of her ass. She pushed back against my face as I worked my tongue against her puckered hole and she slipped a hand between her legs and began stroking her pussy. As her excitement mounted she began rocking her hips, I had to hold onto her hips to keep my face pressed against her cheeks. "Deeper." She hissed as she began to rock harder. I pushed my tongue into her as far as it would go. I felt her body shudder and her ass clench as she climaxed. She then slumped down on the chair. "Mmmmm, that was good." She sighed.