tagTransgender & CrossdressersEmily and Steve Ch. 05

Emily and Steve Ch. 05


Emily, my beautiful blonde transvestite girlfriend and I were on our first out of town weekend trip as a couple. Emily had taken me up to a friend's farm, where we were going to go horseback riding. While I am pretty much a city slicker, Emily grew up in the country and had missed getting out and riding.

We arrived Friday night, and after an excellent dinner with Emily's friend Tessa and her husband John, Emily and I fell into the bed early for a very passionate session of love making. I woke up the next morning naked with my stomach covered with a crusty layer of cum from the previous night. How much of that was my cum versus how much had spewed from Emily's beautiful cock, I wasn't sure.

Emily was already up, and I could hear the shower going in the bathroom. I got up out of the four poster bed, stretched and walked over to the window. It was a beautiful looking day - blue skies with just a few white, fluffy clouds in the skies. I was still looking out the window when Emily walked in the room, wearing a towel around herself, her wet blonde hair hanging straight down. She walked over and kissed me.

I pulled her close to me. "Mmmm, ready for some early morning love?" I asked, tugging her towel off her slim body.

Emily laughed and slapped playfully at my hand. "How do you have any energy after last night?" Emily ran her hands down my chest and across my abs, and gently flicked my hardening cock. I moved close to kiss her.

Emily pulled away. She laughed and pointed at my hard cock. "Sorry Steve, but you'll have to take care of that yourself, and you'll have to do it quickly. You have 15 minutes to get dressed so we can have some breakfast and get out on the trails." Emily picked up her towel and started drying her hair as she walked over to the dresser. She opened the dresser drawer and started pulling out clothes to wear.

"Are you serious?" I asked.

"Yes! Get in the shower. We have to get out early, otherwise we won't have enough time to do the trail I want to ride."

I grabbed my clothes from the dresser and went reluctantly to the shower, mumbling to myself. "Supposed to be a nice, romantic weekend and now we have to go stupid horseback riding." I showered, cleaning the cum off my stomach and managed to whack myself off in the shower. I dried myself and got dressed in my jeans, t-shirt and a pair of running shoes.

I walked back into the bedroom, and saw Emily dressed in a tight pair of jeans, black t-shirt and a pair of cowboy boots. On her head she was wearing one of those straw-weaved cowboy hats.

"Oh wow," I said. "Those mid-west farmer's daughters really make me feel alright! Are you sure we don't have time to let this cowboy ride you, cowgirl?"

"No, silly. Come on, let's get going."

I moved up behind Emily and pressed my crotch against her ass, saying, "I'd much rather mount you then any stupid horse."

"Try it and you'll find I'm a bucking bronco and you'll get thrown off," Emily said, and walked towards the door. She turned back and looked at me. "No, no, wait. That won't do at all. You can't wear those shoes."

I looked down at my footwear. I can't get laid, and now she's insulting my shoes? What the hell?

Emily opened a drawer and pulled out two boxes. "First, you need to wear something on your feet that is better for horseback riding." She opened one of the boxes and pulled out a pair of leather cowboy boots. "Put those on, buck-a-roo." I sat on the bed, pulled off my sneakers and pulled on the cowboy boots.

"Next, it's pretty sunny out -- you'll need something to protect your head." She opened the second box and pulled out a black, suede cowboy hat. She walked over and put it on my head. "Now you look like a man whose fit for this cowgirl," she said, and kissed me. She pulled away and smiled, a big, happy grin.

"You're really looking forward to this, aren't you?" I asked.

"Yes, I haven't ridden in ages. I'm so excited, especially because I get to share it with you."

Okay, that made me feel like a complete heel for mumbling in the shower and calling horseback riding stupid. I remembered how important this was to Emily. My libido could wait. "Alright," I said, "let's get on the trail."

After a big breakfast, we headed out to the barn and John brought out our horses. John handed us the reins, "Emily, you'll be riding Denali. Steve, you'll be riding Daisy."

"Daisy? Doesn't sound very manly," I said.

"She's a good horse, especially for a beginner," John said. "And between you and me, I think Daisy has a thing for Denali, so she'll stick close to the ass of Emily's horse. That way, you won't get lost." John and Emily laughed. I was starting to feel like a big loser.

Emily hoisted herself up on Denali. "Don't listen to John, he just likes teasing beginner riders. It's kind of like an initiation ritual."

John nodded. "Sure, that's it," he said, smirking.

As I tried to get myself up onto Daisy, under my breath I kept reminding myself, "Remember, this is for Emily. She really likes this. You're doing this for her." I couldn't figure out how to get onto the horse, but John put his hands on my ass and pushed me up. I nearly fell off the other side of the horse, and about 5 times in the next 5 minutes nearly toppled over. Eventually I seemed to get my balance, and we were ready to go.

John pointed off in the distance and started giving Emily directions, "just head out to the east gate, that'll put you in the national park and onto the Valley Trail. From there, you can ride up to the Marsh trail. Take a right, and about 2 miles you'll see the Mountain trail on the left. Once you get to the second clearing, you'll see a very small trail off to the south. That'll take you to that secluded lunch spot I told you about. Have a great ride." With that, John slapped Denali on the butt, and the horse started riding away. Just as John had predicted, my horse Daisy, followed Denali diligently.

We rode for a few hours, and once I figured out how to sit on the horse without either crushing my balls or having my ass pounded by the saddle, it was actually kind of nice. John and Tessa's farm borders on a national park that allows horseback riding on some trails, and there was some amazing scenery. From the pastoral fields of John and Tessa's farm, we moved into a wide open valley of tall grasses. We followed the trail as it moved into a forest, and then along the banks of a large pond and marsh. Once we turned onto the mountain trail, we started climbing uphill.

We saw only a few other people on the trail, mostly hikers who moved aside to let us pass. As we climbed, the scenery became amazing, allowing us to see the expanse of the forested national park and the patchwork of farmlands beyond there.

Despite the fact that I was riding, I found myself getting hungry. I looked up, and noticed the sun was getting high in the sky. I called ahead to Emily, "how long until lunch?"

"Steve, you are always thinking with your stomach! We're probably another 15 minutes to the clearing where we head off this trail, and then it's another 30 minutes to the picnic spot that John and Tessa suggested. It'll be nice. It has a great view and is very secluded."

Despite Emily's prediction, it was another 30 minutes until we found the clearing where John said to turn off. The trail we started riding on next was narrow and uneven, and the horses had to slow down and take care with their footing to miss the rocks sticking up out of the trail. I was getting famished and a little concerned as the trail narrowed even more and I found the branches from the trees slapping me as I rode by.

"Are you sure this is the right way?" I asked as a maple tree nearly whipped my cowboy hat off my head.

Emily seemed unfazed by the jungle thickness of the forest. "Yes. We are almost there, I can see the sun from a clearing up ahead."

10 minutes later we arrived at a clearing at the peak of a hill. There was a sharp drop off to the south, and it provided an amazing view of the country side, including a meandering river off in the distance. The clearing was bathed in the noon-day sun. We tied up the horses to a tree near some long grass and a small stream so they could eat and drink. From the saddle bag on Denali, she pulled out some Tupperware, a large thermos and a blanket. "I figured seeing as you liked the picnic we had in the office that one day, you'd like another one."

We laid out the blanket, and I fell upon the food. I devoured the sandwiches and salad that we had, ate two brownies and a few big handfuls of trail mix in record time. Emily laughed at me, she was still eating her first sandwich by the time I was done.

"I can't believe how hungry I get from just sitting on a horse," I said.

"It's more work than you would think, isn't it?" Emily said. "Are you thirsty?"

"Yes, very," I said, suddenly realizing my throat was as dry

"Well, I didn't bring any champagne this time, as we didn't have a way to chill it. But there is some cider in the thermos. It's got a bit of kick." I opened the thermos and poured it into the two plastic cups we had brought.

As we drank our cups of cider, Emily gave me a lesson in the nature of the area, pointing out different plants and birds. Soon our cups were drained, and Emily poured us two new cups.

"Whoa, I think this cider is going to my head," I said.

"It's homemade by Tessa and John. I think it's pretty strong," Emily said, taking a sip.

"Is it safe to ride the horses if we are drunk?" I asked.

"It'll be fine. They know the way home better than us."

We lay on the blanket drinking our cider as Emily told me about her love of riding as a child. "It was one of the few times when I could get away and feel like myself. I always felt a big uncomfortable as a boy, but on the trail I could just be a rider. That's why I love it so much."

"Do you think you'll ever live full time as a woman?" I asked.

"Yeah, I hope so. Probably. I'm not quite ready yet, though."

"Well, whatever you decide to do, I want you to know that I support you fully," I said, stroking her hand.

Emily smiled at me, and leaned in for kiss. We kissed, and slowly moved closer until our bodies were pressed up against each other. I felt Emily reach down and unbutton my jeans. I grabbed her ass and pulled her against me. We started undressing each other. My hat, jeans, boots and shirt were quickly discarded, and Emily pulled my boxers off with such force they almost ripped. Emily took off her boots and jeans, and started to remove her cowboy hat.

"No, leave the hat on," I said. She smiled, and pressed it back firmly down on her head. We continued to kiss, me completely naked and her wearing nothing only her hat, t-shirt and panties.

Emily pushed me down until I was lying on my back. As we continued to kiss, I felt her legs move in between mine and start to push my legs apart. She moved her knees underneath my tights, and pushed my legs up into the air. I felt her hand move down and start to stroke me cock. Her other hand moved under my right leg, and lifted it up until it was positioned over Emily's shoulder. The hand that was stroking my cock moved down, rubbing my balls and tickling my taint. Soon I felt Emily's finger start to press against my asshole. It resisted for a moment, but soon opened up and let her finger inside me.

I moaned as Emily started to finger fuck my ass. I moved my other leg up over Emily's other shoulder to give her better access. My asshole opened up wider, and soon Emily had two, then three fingers inside me. I started stroking myself.

Emily pulled her fingers out of my ass, and removed her panties. Her cock was hard and red. She moved it close to my asshole, and started rubbing the tip of her cock up, down and around my asshole. Emily let go of her cock, and thrust three fingers back into my asshole. It was open wide. Emily removed her fingers, and pressed the tip of her cock against my ass.

"I don't usually do this," I said, and that wasn't a line. I'd only once before tried being fucked, and it was not a very pleasurable experience. Usually I'm on the giving end.

"Do you want me to stop?" Emily asked. I felt the tip of her cock against my ass. I pressed myself against it, and it started to enter.

"No, I want to share this with you." I said.

Emily kissed me tenderly. "I'll go as slow as you want. If you want me to stop, just say, okay?" She pressed herself into me. At first it hurt, but as soon as the tip was inside and I felt her shaft sliding into me, I felt a pulse of pleasure wing through my body. I moaned and closed my eyes.

"Are you okay?" Emily asked.

"Yes, it's good. Fuck me." Emily pushed deeper into me. Another pulse jetted through my body. I lost my breath. My cock quaked, and I thought I was going to cum right then.

Emily started pumping into me, at first very slowly, but I soon found myself bucking myself against her, urging her to go faster and deeper. Emily's pace quickened, and her breathing deepened. She pushed her cock deep into my ass.

"Yes, yes! Fuck me." I said, barely audible due to my lack of breath. I stroked my cock, waves of pleasure continued to grip my body. "Oh, it's so good. So good. Fuck me!"

Emily started pumping faster and her breath quickened.

"Come in me," I said. "Yes, please, come in me!"

Emily pumped my ass rapidly. She tossed her head back and let out a yelp. I felt my ass start to fill up with her hot cum. The feeling was too much for me, and my own cock started to shot out, the cum flying all over my chest and even up onto my chin.

Emily slowed her pumping, and then pulled out of me. She feel on top of me and we kissed. I could still feel my asshole winking open and shut, and felt drips of cum start to run down my ass crack.

Emily held me tightly. "Thank you for sharing that with me," she said.

"I must say I'm surprised, but it really was my pleasure," I replied.

Emily rolled over and stared up at the sky. "Blue skies, country air, a beautiful horseback ride and an amazing intimate experience with the man I love. This is really one of the best days I've ever had," she said.

I smiled and held her hand. I didn't say anything at the time, but that was the first time that Emily had said that she loved me, and I was aglow with the emotion. In addition to her fucking my ass opening up a whole new dimension to our sex life, I knew that this was a big step in our relationship.

The next step, I knew was for me to tell her how I felt. By this time I was sure that I loved her too.

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