tagTransgender & CrossdressersEmily and Steve Ch. 04

Emily and Steve Ch. 04


Emily and I were sitting on the couch watching TV. I flipped impatiently through all the channels, finding nothing on as usual. "Oh wait," Emily said, grabbing my arm. "Turn back to channel 53." I flipped the TV back to channel 53 to some TV show about horses.

"I love horses," Emily said. "I grew up in the country, and we used to go riding all the time. I haven't gone riding since I moved to the city. Do you like to ride horses?"

I looked at Emily confused. "Is 'riding horses' code for some cool sexual position?" I asked.

Emily laughed, "no, I'm serious. Horses, like the animals. And riding them, like with a saddle. For transportation from one place to another."

"No, I've never ridden a horse in my life." I think the closest I've ever been to a horse was one time I did a brewery tour, and they had those big horses that pull the beer wagons in some stables.

"Oh, Steve, you know what we should do this weekend? We should go horseback riding! I have a friend who has a farm about an hour outside of the city where we could get some horses and go riding. It'd be so much fun!"

Now I had no desire to go horseback riding, and almost replied, "I'd rather stay home and go bareback riding with you, Emily," but when I looked at Emily and saw her face so joyful, I couldn't say no.

Emily made the arrangements. We would leave work early on Friday, quickly go back to my place to Emily could change and head out of town to her friend's farm. We'd stay over Friday night and Saturday night, going horseback riding on Saturday, and come back to the city on Sunday. Her friend's farm bordered on a national park which had trails that you can ride horses on, so we'd have lots of places to ride.

I wasn't really very excited about the horseback riding, but this would be the first time Emily and I went on a trip together. We usually spend the weekends together, but Emily is a little afraid to go out dressed as a woman during the day, so we often either just stay inside, or if we go out on the weekend's we go out as two guys. This would be an opportunity for Emily to spend the entire weekend dressed as a woman, and for me to spend the entire weekend with my girl.

We left work early on Friday, and arrived at my place. I changed out of my shirt and tie into some jeans and a t-shirt while Emily was in the washroom feminizing herself. She walked out of the bathroom wearing a pair of tight jeans and a t-shirt cropped to show off her flat stomach. Her blonde hair was cascading in waves down to her shoulders, and she was wearing a very natural makeup look. Usually when we go out, it's to a club so Emily dresses up. It was very hot to see her dressed in a casual but sexy look. We hit the road and after putting up with some mind-numbing slow traffic, eventually were out of the city and cruising along country roads. The windows were down and Emily's blonde hair was blowing in the wind. As we drove by farms with rolling green hills dotted with cows, Emily slipped a CD into the player in the car. Shania Twain came pouring out of my speakers.

"I didn't take you for a country music fan," I said.

"When in Rome," Emily said, laughing, and soon she was singing along with Shania. "Any man of mine still better love me, even when I'm ugly."

"I don't think it would be possible for you to be ugly," I said.

Emily laughed and gave me a peck on the cheek. "You're so sweet. A liar, but at least a sweet liar." I didn't think I was lying though. I've never seen Emily look bad. She even looks hot when she wakes up in the morning.

"The farm is just up here on the left," Emily said, pointing to a place with gorgeous green grass bounded by white fencing. I turned left and we proceeded along a beautiful tree-lined drive towards a set of buildings, including a beautifully restored turn of the century farm house. Behind the main house, there were a few other buildings, including a big, red barn.

"My god," I said, "this is like what a movie set farm would look like!"

Emily laughed. "Tessa and John have put a lot of work into this place. 5 years ago this place was an overgrown dump that was practically falling apart."

I parked the car and we headed towards the main house. A young couple came out to greet us. Emily and the woman hugged while the man came over to shake my hand. "Hello, I'm John," he said.

"I'm Steve. Thank you so much for having us up this weekend."

"Oh, don't worry about it at all. It's nice to have guests," John said smiling.

The woman and Emily had stopped hugging, and Emily brought her friend over to meet me. "Steve," Emily said, "this is my friend Tessa."

Tessa embraced me, and after a nice hug, moved back and held me at an arms length, looking me up and down. "Hmm, he seems cute enough. Does he treat you well?" she asked Emily.

Emily blushed, "Tessa! Please, Steve is a great guy. You don't need to protect me!"

Tessa laughed. "Okay, let's get inside and get you settled."

John and I grabbed the luggage from the car as Tessa led Emily into the house. John and I followed them into the house, and up the stairs to the spare bedroom. The bedroom had wooden floors and wooden furniture that matched the floor boards, including a giant four-poster bed.

John and I dropped the luggage on the bed, and then he and Tessa moved towards the door. "We'll let you two get settled in. There are some towels on the dresser in case you want to have a shower before dinner," Tessa said. "Dinner will be ready in about 45 minutes, so you have some time to do... whatever," Tessa winked and then closed the bedroom door.

Before doing... whatever, Emily and I unpacked our bags into the dresser. "Tessa seems really nice," I said.

"Oh, she's great. We've been friends for a long time. She is one of the only people I went to school with who I could tell my secret. She's actually the first person I told that I really feel like a woman. I was really scared, but she was so accepting of it. When I told her, she said, 'this is so cool. I have another girlfriend to borrow makeup and clothes from,' and then she hugged me."

"I'm glad we have this opportunity to spend the weekend together with you being so comfortable," I said, pulling Emily close to me. We started kissing, and my hands worked their way down to Emily's ass. Emily started to grind against me.

"So, Tessa said that we have 45 minutes before dinner. What kind of trouble do you think we can get into in that amount of time?" Emily asked. I responded by picking her up and tossing her onto the bed. She laughed as I launched myself on top of her.

"I'm sure I can think of something," I said as I unbuttoned her jeans and tugged them off her hips. Emily wasn't wearing any underwear, and her cock was already getting hard. I stroked her as we French-kissed. Emily moaned as my hand moved up and down her shaft and my tongue moved around her mouth.

Emily laid back and pushed her crop-top shirt up to expose her chest. She started playing with her nipples as I continued to stroke her off. Our kisses were becoming deeper and more passionate. I continued to rub my hand up and down her cock. It was rock hard by this time, and as I reached the top, I could feel it moistening with pre-cum.

Emily broke off our kiss and panted, "Faster. Stroke me faster." Our lips met again as I started to stroke her faster. Her hips bucked up to drive her cock deep into my hand. She started to pump up and down, driving my hand up and down the entire length of her shaft. With her hands, she was tugging and pulling at her nipples. "Oh god. I'm going to cum!" she moaned. Her hips started to shudder as she lost her rhythm, so I started to pump her furiously. I felt her lips trembling against mine. She grabbed her nipples and squeezed them. "I want to taste you," I said, and put my mouth up to the tip of her cock. My hand still pumped her shaft up and down. I flicked my tongue against the tip of her cock. I felt it quiver. Emily grunted and her hips thrust upwards. Streams of hot cum came cascading out of her cock. Most of her juice went into my mouth, but her cock shuddered wildly, and soon there was cum on my face, my neck and my t-shirt. I licked my lips and get as much of her cum as I could, and swallowed it down.

Emily let her hips sink into the soft bed, closed her eyes and sighed. I moved up and kissed her gently on the lips. We kissed for a few moments, and then Emily opened her eyes. She looked at me, smiling.

"We should get ready for dinner," Emily said. She then noticed the cum on my t-shirt. "I guess you need to change your shirt," she said, laughing.

I changed my shirt, and we headed down for dinner. It was a very good dinner, and the four of us had a great conversation. When John and Tessa got up to get desert, Emily leaned over, grabbed my crotch and whispered in my ear, "I realize that we never took care of you before dinner. Don't worry, you'll have a good time once we get back upstairs." Emily squeezed my cock through my jeans and put her tongue in my ear.

Just as Emily broke off from me, Tessa and John returned to the dining room. "I hope you like chocolate mousse!" John said.

The anticipation of what was to come was hard to take. I could barely concentrate on conversation during desert. It's probably the first time in my life when I really wished I could have skipped desert and gone right to bed.

Emily, though, made sure the wait was worth it. She always does.

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