The Trip

I’d been seeing Joe for most of the summer and in that time I had starred in maybe a dozen or so of his private home movies. My hair had grown maybe another inch, I’d had my ears pierced and my eyebrows shaped, as far as my parents were aware it was because of a drama club I’d joined, where a part dictated the sacrifice, it was a poor excuse but they chose not to question it further.

One Sunday night I got a telephone call from Joe telling me to come over right away, I dropped everything and did as I was told. When I arrived at Joe’s he ushered me straight up to his bedroom.

“Were going away for week,” he said

“Pardon?” I stammered

“It’s OK I’ve already cleared it with your parents, I told them it because you’ve been helping me with some PC projects over the summer and its my way of repaying you. Now what do you say”

“Thank you Master”

“That’s a good girl, a friend of mine will be joining us for the trip and it’s important that you extend to him the same courtesies as you do for me, do you understand”

“So I guess I’m just your toy for the week then?”

Joe grabbed my hair and pulled it back positioning his head next to my ear

“I said, do you understand?”

“Yes Master” I replied

“If there is any back chat or refusal on your part, then I think you know by now that there will be repercussions”

“I wont disappoint you master,” I promised

“I would hope not, we’ll pick you up at ten tomorrow, just pack your toiletries, everything else will be taken care of”

I left Joe’s in a daze, walked back to my house where my parents were excited for me, it was my first time away from home that wasn’t a f****y holiday, they told me to be on my best behavior. I promised them I would be and went upstairs to try to get some sl**p.

The next morning, I awoke and showered as normal, I threw my toothbrush and shower gel into a bag and walked back into the bedroom, I threw on my old jeans and a baggy T-shirt along with a pair of boots. The guys pulled up to my place at 10am sharp.

I walked out to Joe’s car with my little bag of toiletries under my arm, as I got into the car Joe introduced me to Chris, I’d seen him around town before, he was black, about 6ft 4, athletically built, and smiled at me as I climbed into the back seat.

“You look as good as you do in your videos” Chris said

I felt my cheeks going red, Joe’s tapes were supposed to be private, but I thought better of saying anything, so early into the trip.

“Right, we need to stop and shop along the way, pick up the day to day wear that our little Kara is going to need. I've already got a special bag packed for her,” Joe said. “Let’s get this show on the road!"

A couple of hours later, we pulled into a large retail park. It was lightly snowing as I followed Joe and Chris around sheepishly as they selected clothing for me. We bought some jeans, a few dresses, hiking clothes, workout clothes, sweaters, and tennis shoes at the sporting good store. At a shoe store, the purchases included a pair of gothic Mary Janes, a pair of knee high black boots with a 4" heel, a pair of slippers, and a pair of red court shoes. Joe told me he'd already bought a few outfits from the adult store that he thought I'd enjoy, but he also wanted to get a few more casual clothes.

After that we went into a lingerie store. Joe thought it would be funny to ask one of the salespeople to take me in the back and get my measurements, she tutted as she looked me up and down but then seemed to take an almost perverse pleasure in doing as Joe had asked. We picked up panties, camisoles, bras, suspender belts, stockings, bustiers and a couple of corsets. The bill came too over and grand.

“It’s OK baby, you’ll find a way of paying us back, it might take you a few years but eventually you’ll manage it” Joe smirked “Here's your next task. Take the jeans, the pink T-shirt and the boots we just bought and find some place to change"

"I can’t travel the rest of the way like that people will know I'm a guy, at least let me change once where we’re going." I protested

Joe grabbed my arm forcibly.

"Listen bitch, you can either change here, or ride the rest of the way in nothing but a smile. Either way, your male clothes end the trip here. It's your choice."

“You’ll need these as well”

Joe handed me a bag with a baby pink bra and matching panties in it, I found a public toilet over the other side of the car park and, after locking myself in one of the stalls, stripped off my boots, trousers and sweatshirt. I slid on the bra and panties and stuffed the cups with toilet paper; I slid the T-shirt over my head. It was tight across the body, shoulders and arms, and it didn't leave much to the imagination. Next, I slid on the jeans. I was thankful that the guys hadn't f***ed me to wear a skirt. But as I slid them up my legs, I realized that since they fit so snug, I'd have to tuck my dick back between my legs. That was a little uncomfortable, but once they were pulled up, it held fairly well. I slipped into the knee boots and zipped them up over the jeans. As I exited the restroom, I couldn't help but catch myself in the mirror, I quickly tussled my hair into something more girlish.

All ready to go?" asked Joe.

My answer was only to hand over my male clothes; I tottered over to the car, my heels slipping in the fresh snow and climbed into the back seat. I crossed my arms petulantly as I watched Joe dump my clothes into a waste bin and tried to ignore the guys as we started on what I hoped would be the last leg of the trip.

“There’s another little present for you in the bag on the back seat” Joe said “But considering how you’re acting I’m not sure you deserve it”

I reached into the bag and pulled out a pair of breast forms, I sat staring at them for a minute.

“They should be the right size for your frame and they will feel a whole lot better than toilet paper” he said with a smile

I pulled up my T-shirt and swapped the toilet paper in my bra for the breast forms, they were cold at first but soon began to warm up, the new weight was a strange sensation and it took a little while for it to become comfortable.

“Now what do you say?”

“Thank you master”

“Good girl, just remember to keep your attitude in check and you never know you may just end up enjoying yourself”

As we drove for the next couple of hours, we listened to music and I tried to read a magazine. Listening in to the small talk between Chris and Joe, hoping that I might get some clue of what I was in store for. I guess I must have dozed off, because next thing I knew, we were pulling up to a solitary cabin nestled in the woods.

“You see baby, nobody around to hear you scream” Joe said

I looked at him trying to work out if he was joking or not, luckily Chris started laughing.

“I think you scared her,” Chris said

Joe threw me a look as he opened the front door to the cabin

"Kara, if you take the back bedroom. I'll take the master bedroom off to the left. Chris, you get the front bedroom. Hustle up and let's get everything inside, it’s bl**dy freezing" said Joe.



We really only had to take in their luggage and my shopping bags. There wasn't any food in the house.

"I'm going to run out and grab us some food for the week," offered Joe. “Then I’ve got a couple of errands to run, if you two want to get comfortable I’ll be back around 10ish”

With a wink and a nod, Joe took off. Chris smiled as he looked at me then disappeared with his bags into the front bedroom. I carried mine into the back bedroom, and then skulked my way back to the sofa. I really didn't want to know what Joe and Chris had planned but it really didn't matter. I already knew that I was in for a degrading week. After about 30 minutes of watching bad TV, Chris finally emerged from his bedroom with a bag in hand.

"Here you go Kara. These are some of the things that I brought from home for you. Now it's not everything, because I wanted to keep a few things as surprises"

I looked in the bag; it seemed to be a few cosplay costumes, a Japanese school uniform, a maid’s outfit, and some underwear

"So basically, I'm your slave for the week." I asked him.

"You’re a quick learner Kara, I’m beginning to see why Joe likes you" Chris said.

Chris poured a large drink out his hip flask and handed it too me, I took a big gulp and felt the warmth spread out through my body.

"Don't worry about anything. What happens here stays here, now what do you say we take things slowly"
Chris took my hand and walked me through to his bedroom

“Strip down to your bra and panties” Chris instructed

I did as he said, stood there in my bra and panties, Chris gestured to me and I moved around the side of the bed and crawled onto it. I buried my face into the pillow and tucked my hands underneath it. I heard him taking off his clothes. By the time he got close, he was wearing only his boxers.

I closed my eyes and waited for him to make the next move. I smelled it before I felt it. It was the scent of perfume. He climbed onto the bed straddling me; I felt lotion being spread on my back. I felt his hands kneading the muscles in my back; I tensed up slightly at his touch.

"Relax" was all he had to say.

He spent a few more minutes working on my shoulders and arms, and then started working his way down my back. I felt him spread more lotion on my lower back as he neared my hips and ass. He slid my panties down off my bum, exposing my cheeks and began to massage my lower back. I felt his fingers dip into the crack of my ass and just lightly probe my hole before he continued past it and started working on my legs. Slowly and methodically, Chris worked the muscles of my legs and involuntarily, I felt a moan escape my lips.

"So you are having fun then?"

I didn't say another word. I was still somewhat dazed by Chris's outpouring of gentleness and caring, was he trying to seduce me, this was certainly not what I had come to expect from my treatment by Joe. I started to relax and began to enjoy the sensitivity with which he treated me.

"Roll over," he said.

Slowly, I rolled over onto my back, feeling relaxed and tingly. I was so relaxed I was fighting to stay awake. As he got closer and closer to my groin, I felt myself start to harden, even while tucked.
The next touch surprised me. Chris started to spread my legs and he pulled my penis loose. His lotioned hand started to stroke it slowly, gliding up and down, before stopping and continuing to massage my front, thighs, hips, stomach.

Chris pulled himself away and I heard myself utter a moan of a disappointment. I couldn't believe that the sound came from me, but a part of me didn't care.

"If you're enjoying yourself more than you thought you would, just nod."

I nodded slowly.

"Good," he said. 



I felt his weight come back on the bed; he spread my legs wide and positioned himself on top of me. I felt his breath on my neck. Then, a nibble on my left ear, a little tongue darted into my ear causing me to giggle , a gentle kiss on my forehead, a light tonguing of my right ear.

I could feel his dick pressed against my balls. I could feel his stomach pressed against mine. I reached out and felt his arms taut, supporting his body. I felt his kiss on my lips. Lightly he kissed them. His tongue caressed my lips and parted them. I responded to his kiss as though I had no control over my own body. Deeper and deeper he kissed me and I felt myself rising to meet him. I wrapped my arms around his back. 



We continued kissing and rubbing our bodies against each other for a few more minutes before I felt Chris pull away again.

"Roll over, lay on your stomach."

I did as asked, Chris grabbed a pillow and positioned it beneath me pushing my ass into the air, and I felt him spreading my legs as he positioned himself between them. I felt his hands on my ass, spreading my cheeks apart so he could find my hole. As he started to tease my hole with his fingers, I felt the coolness of the lotion dripping in. I tried to relax as he slid his fingers in, first one, then two, then three. I squirmed and he used his other hand to put pressure on my lower back, keeping me in place. I started to breathe harder as he finger-fucked me for a few minutes.

"Are you ready?" he asked

"Ready for what?" I replied

Only I didn't get all of my answer out because right in the middle, Chris started forcing his entire hand into my ass.

"Wait...wait...wait..." was all I could manage to get out.

Even though he was going slowly, the pressure was amazing and I had never been stretched quite like that.

"Oh God, that's too much" I moaned into the pillows.

But Chris didn't stop. He pushed, added lotion, and then pushed some more until his entire hand was up my ass. I didn't move. I just lay there reveling in the mix of pleasure and pain as I felt Chris clenching and relaxing his fist inside me. 



"I'm pulling out now." He said

He did just that. Slowly, gently, he removed his hand and I was left shuddering on the bed trying to get my mind around the fact that I had just had another man's hand up my ass.

Chris stood up and removed his boxers, I gasped again, I knew the stories but my god he was huge, he noticed me staring at his package.

“That’s why I had to loosen you up first, I didn’t want to do you any permanent damage” Chris said “Well at least not on the first night”

Chris rolled me onto my back and moved on top of me pushing my legs up onto his shoulders, he gently eased himself into me. Slowly, almost lovingly, Chris began fucking my ass. The sensation was intense, he felt so big I was having a hard time telling the difference between his cock and his fist, the pain was intense but in a good way, I didn't feel like I was being assaulted, I felt, sensual. Feeling his weight on my back with his massive dick in my ass, I wanted to move against him. Even as he fucked me, his hands caressed my arms and pulled them above my head where he intertwined his fingers with mine. His fucking was slow and luxurious and I started to moan in time with his thrusts

"That's good honey, that's good,” he whispered

Chris started pumping faster and his pressure on my prostate made me feel like I was going to burst.

"Please…please...quick...can't hold on..." My statements were jagged.

My breath was heavy. My body was starting to shake from the exertion and the pleasure. I felt muscle twitches all over my body and second after prolonged second, I tried to hold on until I could go no further.

I couldn’t believe it as I came all over my stomach. Chris started grunting louder and louder, he came with a bed-shaking, toe-curling orgasm. My mouth was open as I tried to breathe under the pressure. My hips bucked as Chris spurted jet after jet of cum into my ass. After he was done, we lay there for minute after minute, trying to breathe and recover our spent energies. Finally he spoke.

"So...was it good for you?” Chris Said

I laughed. I didn't mean to. I never thought I would. But I did. I giggled and said

"Yes."



"See what can happen when you just relax?" he added

I could see the smile on his face as he spoke. Slowly, he let go of my hand and began to trace the outline of my body with his finger. I shivered at his touch, but I longed for more.

"Kara, honey, that was fantastic” he said

I lay there on the bed, embraced in his big strong arms, before the tiredness overtook me and I dozed off.

100% (26/0)
 
Categories: Shemales
Posted by kara_zor_el
2 years ago    Views: 1,408
Comments (4)
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10 months ago
Very Sexy Story ;) xx
2 years ago
You don't need a blog. You need a book deal. You could make millions. Am throbing thinking about the next story.
2 years ago
great story girl!
2 years ago
mmm nice!!!