Drifter to Housewife

The sun was starting to set, I was getting sleepy and decided to find a place to stop for the night. I already knew how much cash I had on me and it was not much and I had even less in my bank account. So I did what I always did in that situation: I stopped at a Walmart. Not my first choice no one of course not but when you are broke you do what you can. I was still ok on gas so no big deal there.

I pulled in and went to the back of the lot Walmart usually did not care if I stayed overnight. Hell, I could see an RV parked for the night not far away but since covid things had got more sticky, with the fact that they were no longer 24 hours.

I went inside and got some food, the cheapest stuff I could buy and went back and ate my meager meal. And started to block out the window. I left the keys on so I could listen to the radio for a while.

Maybe I should explain why I'm here. Firstly, I'm not sure where here is I tend to drive randomly. I might stay in a town for a day or two checking craigslist for people looking for day labor to make a few bucks here and there. I would have to do that here. About a year ago my parents had both died of covid, being their only son I had sold all their stuff: the house, their cars. Then I decided to get in my truck and drive. Where? Who knows, when will I stop? Again who really knows.

I still had a sizable amount left from my parents, but I had wisely kept that separate from my finances for this trip only pulling from it when the truck broke down or when I needed some medication or another.

It was a good life so far and I felt liberated, but I did have issues. I mean I could have settled down, I have a degree after all but nope here I am me my truck and the open road.

I woke up sticky with sweat, I opened the door to a hot muggy day, I groaned and grabbed my phone and started to scroll through craigslist looking for a day labor job. I found one for house cleaning. It looked decent and at least it would have AC so I called the number associated with it.

"This is Jake Thorton speaking.". Said a man when someone picked up.

"Mr. Thorton, this is Carl Jones, I am calling about your ad on Craigslist?"

"Oh yes of course, I just put that up I was not expecting anyone to call so soon. It just some basic house cleaning and maybe some cooking, it seems some of that has gotten away from me while we have been in this mess."

"I can understand that, when can I come over?"

"Right now if you want." After assuring him I would be right over I went straight there. He was standing at the door when I pulled up. He was a tall man at least 6'2 and looked like he worked out, he was maybe forty five or so with brown hair cut short. Compared to me I was barely 120 pounds soak and wet with fair skin and red hair, and green eyes. Plus I was just barely 5'6. He smiled not unkindly.

"You look like you are on the road a lot." I explained my circumstances and told him I did have people I checked in with every couple of days (it was always good to mention that with this sort of thing, I admit drifting and doing odd jobs is not the safest idea and would not recommend it) he merely nodded, said I could take a shower before I cleaned the tub it I wanted.

So I did, I started there and cleaned the rest of the house. There honestly was not much to clean though, his house was in good shape. But nevertheless I earned my pay. And pay me he did handing me a big wad of bills. Enough to keep me going for a month.

"This is way more than I thought you would pay me Mr. Thorton." He nodded.

"I believe in paying well for good work. You did everything I asked and more so you get paid accordingly" I grinned.

"Well I appreciate it."

"Are you hungry? I know a good burger place just down the road. If you want to join me, my treat of course." I did not know what to say so I just nodded.

We talked for what seemed like hours at the small burger place. I had been right he was about forty five and divorced, his ex had then died of covid like my parents. His kids were 18 and 19 respectively so they were making their own way in life. He worked for an office and he used to go in but it was now all remote so he had way more time at home just did not enjoy cleaning, or cooking so he decided to hire someone for the day and see what he thought of it.

"So Carl, you have been on the road for a long time, what if I let you move into my spare bedroom for a month so that way you can get off the road for a bit and relax. I'll pay you 800 a week and all you have to do is clean and cook for me." I thought about it, a month off the road would be nice.

"Alright Mr. Thorton you have a deal." I reached out to shake his hand.

"Please call me Jake."

So that's how I ended up living in Jake's house in his spare bedroom. Well one of his spare bedrooms he had three bedrooms and four bathrooms. A week turned into two turned into a month turned into three months. It was the longest I had ever stayed with anyone since my parents died. Honestly it felt kind of good to just be off the road and all he ever asked me to do was pick up around the house and sometimes cook. We had long conversations late into the night sometimes.

It was a fairly typical day, when I was in his bedroom. I was vacuuming and accidently hit his desktop and the screen which had been blank flickered to life. I only glanced at it as it came to life this was not even the first time it had happened but, rather then the usual windows screen, a website was up. It was a dating site for crossdressers. It was weird he did not seem to be a crossdresser. Not that I minded, his thing was his thing it did not bother me. Yet the more I looked I realized he was looking for a crossdresser. Not one himself, I felt bad. I felt like I had Invaded his privacy. He was the one who had left it up though he knew I vacuumed regularly. Still, I felt bad, that night at dinner something of my guilt must have showed.

"Are you ok Carl?" He asked with some genuine concern. "You seem stressed." The last part was not a question, more a statement of fact. I sighed loudly.

"Look I'm really sorry, but I bumped your computer while vacuuming today and your, uh dating site came up when I did." He sat there for a few minutes.

"Oh" was all he said.

"I mean I don't mind we all have our kinks. I just felt like I invaded your privacy by even seeing it." He smiled and laughed a genuine laugh.

"I'm the one who should be embarrassed Carl, I was stupid enough to leave it up. Yet now you know I'm just a pervy old man" he laughed again in a good natured manner.

"Oh come on Jake you are not that old you are only forty-five that's only twenty years older than me." He grinned and shook his head ruefully.

"I admit I have always wanted to have a sissy housewife around to do things for me but until that time I have you" he laughed and slapped me on the shoulder. I grinned.

"I mean it's not like I'm not already a housewife here." I blushed, that had come out so wrong. He only smiled kindly.

That night I tossed and turned and I could not sleep. I kept thinking about what I had seen and what I had said. The question was how did I really feel about it? I took out my phone, and went to Amazon. In about ten minutes I had made the order.

It took about a week for everything to come in. It had been a long time since I had even considered doing this. Why now, why with Jake? Was I attracted to him? Was I even into men? Maybe it was just the fact that he was showing me kindness after all this time on the road. I honestly had no idea. Maybe it was just a desire to be intimate with someone again?

I had never been much of a ladies man oh sure I had had a few girlfriends, and had had one long term one back in college. Things had not worked out; however, and well truth be told I had not been with anyone in the past four years. And now well it was less likely anyone would want to sleep with a drifter then stories made it out to be. Besides I always felt weird with women like I was missing out on something. I had never been with a man though I guess I was curious about it.

The clothing I ordered came in and it took me about a week before I even had the nerve to open it up. Inside was a green retro style dress a white Petticoat and a matching panties bra and garter set all in a pailer green than the dress. Lastly there was a pair of white stockings. I laid it all out on the bed and debated how I was going to do this. Would I just walk out dressed like this, or would warn him first. I took a makeup kit out of one bag, and opened it up. It had been a long time since I had done my makeup and I was not sure if I could do it again.

I took a deep breath and headed for the shower I needed a, shave a complete shave. I had tried crossdressing several times over the years. I had even had a small wardrobe the year I spent in a dorm without a roommate. My girlfriend at the time had even helped me experiment, when we broke up she told me she hoped I would find what I was looking for. At the time I had no idea what she was talking about. About two hours later I stood in front of my mirror, completely shaved my long red hair done in a feminine fashion. I had on some light makeup, and was wearing my new clothing complete with heels. I walked out to find that Jake was not home. I rolled my eyes but got to work on my normal chores for the day.

Jake came home late that night, something must have gone wrong at work. I figured, he called me on his way home.

"Hey sorry I'm later than usual, I thought I might have met someone on my dating app, but she changed her mind after I drove over there to see her." I blushed.

"Well some girls don't know what they are missing." He laughed. I grinned, knowing that he was gonna find a girl tonight anyway.

He got home about forty five minutes later and almost did not notice what I was wearing. He grinned when he did.

"What's all this?" He asked in a hushed voice.

I smiled and did a small turn for him so he could look me over on all sides.

"Oh I just thought I would try something different. Maybe play around a bit."

"I did not know you liked to, well you know, dress like that." He was blushing himself now.

"Well it's been a few years, but when I saw you on that site I started thinking about it again, and well here I am. You can call me Chloe."

"Chloe" he seemed to taste the name, "I like it, it suits you and that dress matches your eyes well." I smiled. He started to walk up to me, he reached out and paused.

"May I?" I nodded and he took me in his arms and I put my arms slowly around him. He smiled down at me and leaned in and kissed me. I had never kissed a man before. This was completely new for me. I found it different from kissing a girl and I tried to mimic how girls had kissed me, but I could not think too long about it. My lips parted for his tongue and he eagerly slipped it in. We stood making out for what seemed like hours my body pressed against his. His hands started to gently caress my body moving up and down my back and gently brushing my butt, but not outright grabbing. Slowly the kiss broke, we smiled at each other.

My heart fluttered in my chest, as we held each other. He leaned in and kissed me again

I kissed back, pressing my body to his wishing I was more feminine for him. He slowly parted from me. He seemed reluctant though.

"Is everything ok?" I asked him. He nodded but still looked strange. "Are you sure?" He sighed.

"I was just not expecting this, is all. I mean I did not figure you would stay and I did not know you had feelings for me. Now I feel bad for trying to go on that date." I giggled.

"I have always wanted to try this ever since I was 12 and put on the first dress I ever wore. I just saw your profile and thought hey he is a handsome guy why not see." He chuckled.

"So you think I'm handsome" I smiled and this time I kissed him. He took my hand and slowly started to lead me to the bedroom. We started making out and slowly laid out on the bed as we kissed our hands, started to explore each other's bodies. He was slowly caressing me, touching me, seeming to make sure that, where his hand was ok before he touched me there. I did not stop him I did not want to stop him my cock was getting hard in my panties. I unzipped his pants, it felt so natural and I almost did not notice I had done it but, I did not stop there. I reached in and pulled out his monster of a cock 8 inches cut and already hard just from our make out session. The head already glistened with precum. Way bigger and thicker than my five inch uncut cock hiding in my panties.

We kissed again and I started to stroke him. He moaned happily as I did, but he stopped me. He started to unzip my dress slowly pulling it off keeping me in my lingerie, he gasped slowly when he saw it and ran his hands over my bra cups. He kissed me again and pulled me close to him, I could feel his cock against mine, our precum making my panties wet. He moved my bra aside and sucked my nipples for a moment making me moan again in pleasure. I pulled my panties off and took both our cocks in my hand stroking them together. He stiffened suddenly and I felt his cock pulse and his cum hit mine.

"I'm so sorry it's been a long time since I had a beautiful woman touch my cock." I grinned up at him.

"You think I'm beautiful?" He grinned and leaned down kissing me more passionately than before his cock had remained hard in my hand. He took control, spreading my legs under him. He lubed up his cock and lined it up with my hole, he looked up at me. I nodded, he pressed forward slowly the head of his cock entered my body for the first time I had another man's cock in my ass.

He paused as the head entered me and he heard me moaning, it was not pain, it has been a while since I played with myself this way, but I knew I could take his cock. He pressed forward and suddenly he was fully inside of me. His balls slapping my ass, he slowly started to thrust making love to me. It was going perfectly so far, almost exactly how I had dreamed it. He leaned in and kissed me, as I moaned in pleasure.

"Oh fuck Jake your cock feels so good in my boipussy."

"Your boipussy is so tight baby I love it. It's the best, so much better than a real pussy." He moaned and wrapped my legs around him and he kept going. I could feel my pleasure building and with a pop I felt the most pleasure I had ever felt before. My cum exploded out of my cock, and I could feel it racing through my entire body. "Fuck baby you tighten like that some more I'm gonna cum t....." he did not finish his sentence his cum filled my boipussy. And I moaned loudly again as the hot feeling raced again through my body. I barely felt him as he pulled his cock out of me. He pulled me close to him and I laid my head on his chest and his arm around me. I quickly drifted off to sleep.

I did not sleep for long though he had to get up and use the bathroom. He came back and we cuddled close together and started kissing again. My hand wandered down to his cock softly stroking it to make it hard again.

"Will you give me a blow job?" He asked, "I know some girls don't like it." I put a finger on his lips to silence him.

"I am not some girls." I slid down his body till his cock was facing me. I smiled and looked up at him taking it in my hand. "Do you have more cum in there?" I asked flirtatiously, "you came hard twice, want to go for a third time?" I licked his cock head and slowly started to put him in my mouth. I tried to keep my teeth out of the way as I started to suck him off. I felt his hand in my hair keeping me in place. My head bobbed on his cock I started to get hard too, feeling it rise in response to my actions. I reached down and started to jerk myself off. He moaned in pleasure and I picked up the pace on him, taking his eight inches as deep as I could. Swirling my tongue around his shaft.

Sucking harder and harder. I could feel his orgasm building, I sucked harder, his hand pressed down suddenly and my mouth was flooded with his cum. So much it spurted out onto his cock and my chin and chest. With my mouth still on him I started to cum into my hand. I reached up after and showed him he licked it up and I leaned up and kissed him with his still in my mouth. We made out one big cum covered mess, our bodies never caring that we were both males. The salty funky taste of the cum on our tongues and covering our mouths was all we cared about at that moment. I knew my place from now on was to please men this one or if he would not have me others would. My fantasy now filled, I wanted more.