Mr. Hunter's Second Chance Academy Ch. 02

In Seattle, I had decided to take Jennifer on the road with me and use her to test the other candidates. Besides, the best way to find out if you are compatible with a girl is to take a long ride in a car with her.

I had originally only wanted to take in one sub the first year, since I was not really sure what I was getting into. If everything went well, I was going to add a new girl each year until I had a total of three. I would be able to replace each one as they graduated and moved out, thereby keeping my harem fresh. Spending a summer like the S&M version of "Road Rules" however, was too much to resist so I decided to meet the rest of the girls as planned and see what developed. Jennifer did not have many obligations in Seattle and it only took her two weeks to get her shit together and join me in the little coastal town of Florence, Oregon. We bummed around for a few more days and finally made our way down US 101 to San Francisco.

The next applicant on the tour was a young woman named Chloe. I met her at the Presidio while Jennifer stayed at a campground in the RV. Chloe and I had exchanged e-mails and she had sent me several pictures of herself, so I already knew what to expect. As I had hoped, the pictures did not lie. Chloe was everything that Jennifer was not. To begin with, she was much shorter at 5'1" and very petite with strawberry-blond hair. She had green eyes, pale skin and lots of freckles that gave her a younger-than-legal appearance. (She was actually 19 and I had documentation to prove it!)

Everything about her was cute. She had a cute, innocent smile and cute little pear-shaped butt. She wore a pair of faded, skin-tight jeans and an AC/DC concert shirt from the 80's that all but hid her tiny breasts. As much as I wanted to get to work on her, I still felt the need to get to know her and make her feel comfortable. We walked around the grounds talking and flirting until the sun began to set, finding us at the main gate. I had arranged for a cab to pick her up there. I gave her the key to a hotel room downtown and put her in the cab. As with Jennifer, I told her to meet me there in fifteen minutes. She was also given the same instructions regarding the position I was to find her in.

I mulled over Chloe's story as I rode to the hotel in my own cab. She was, as it turned out, not nearly as innocent as I had imagined. Up until six months ago, she had been a Goth girl, her hair had been jet black and the picture on her driver's license proved it. She had several piercings, tattoos and had even done some blood play. She had also been exploring the substantial underground the city has to offer. Narrowly avoiding a world of homelessness, drug addiction and prostitution, she had gotten cleaned up and was looking to make a fresh start in a new city.

By the time I had arrived at the hotel, it had started to rain and the wind cut me to the bone. Suddenly I knew what Mark Twain meant when he said, "The coldest winter I ever spent was a summer in San Francisco."

With any luck, there would be a little blonde waiting to warm me up. When I opened the door to the room however, I was greatly disappointed. Chloe was no where to be found. I figured that she had second thoughts and I decided to go down to the restaurant since I wouldn't be dining in this evening. Jennifer was supposed to be at the room at 10. Since the room was already paid for, I would just go up after dinner and wait for her.

About 8:30, I went back to the room and ordered a movie on pay-per-view. At ten minutes after nine, I heard a knock at the door. If it was Jennifer, she was much earlier than I expected.

"Who is it," I called as I got up and moved toward the door.

"It's me," a small voice replied.

I looked through the peephole and saw Chloe standing awkwardly in the hallway. I opened the door to find her wet to the skin and shivering uncontrollably.

"Jesus Christ! Come in and let's get you warmed up," I said, closing the door behind her.

I pushed Chloe into the bathroom and roughly stripped off her wet clothes, letting them fall to the floor. I would like to have taken the time to admire her body, but at the moment I was trying to comfort her and get some hot water running.

"What happened to our appointment?" I said as I unhooked her bra.

She held it in place with her left arm but did not protest as I slid her panties down her hips.

"I needed some time to think, so I've just been walking around"

"You've had months to think about this," I said, the aggravation apparent in my voice.

"I'm scared. I've never been anyone's slave before and I'm afraid you might hurt me. I got kicked out of the place I was staying and don't have any place to go," she explained between sobs.

"Shhhh, don't worry about it," I said as I cradled her head against my chest. "Let's get you in a hot shower and then into some dry clothes. You'll feel better and then we can talk some more." With that, I helped her into the steaming shower and went to fix myself a drink.

"What the fuck have I gotten myself into?" I asked myself. "I knew I would be meeting some 'wet cats' on this trip but this is fuckin' ridiculous."

When she got out of the shower, she looked much better. The pink hue had returned to her skin and the spark had returned to her eye. Her hair was still wet but it now had a healthful shine. Chloe dropped her towel as I wrapped her in a hotel robe and I was finally able to admire her body for a moment. She had freckles on the slope of her chest all the way down to her puffy pink areolas. Each tiny nipple had a barbell neatly through it but the breasts themselves were quite small. Her stomach had a little curve to it and led down to a mass of golden-red curls. Chloe's hips were a little wide for a girl her size but it made her look more like a woman.

"I ordered some hot cocoa from room service, I hope that suits you," I said as I guided her to one of the chairs in the room.

"Wow, that sounds great," she said, as she sniffed and flashed me a grateful smile.

"I've already chosen one submissive and have decided to interview the rest of the candidates to see if any of you have potential. I may not take any, or I may take up to two more. I do however, have some concerns about taking in a submissive who has no place else to go. This has got to be a decision you make freely and not under duress. Since I think Jennifer should hear this too, I'll wait until she gets here to tell you both what I've decided."

Chloe and I watched the movie in silence as we relaxed and waited. Jennifer and room service arrived about the same time. I let the girls enjoy the cocoa and get to know each other while I showered and changed. When I came out, Jennifer had shed her wet clothes and was wearing a terry cloth robe like Chloe. Their sexy legs peaked out from under their robes as they sat on the bed and it excited me to know that they were naked underneath. I noticed that they were sitting awfully close and Jennifer had her hand on Chloe's knee where her robe had fallen open.

Without saying a word, I reached for my wallet and took out ten $100 dollar bills and placed them in one of the hotel's envelopes. I sealed it and dropped it on the table as I turned to them and said, "I can't take in someone who has no other options. I also cannot kick you back out on the street because of my moral dilemma. Here's what I've decided, and this goes for both of you. If, at any time, you are not comfortable with our arrangement, I want you to take this envelope and leave. This money will buy a bus ticket anywhere you want to go and get you a place to stay long enough to get on your feet."

Both the girls took a moment to think about it, then Jennifer stood up.

"I'm staying with you master," she said as she hooked her arm around mine and looked at Chloe.

The younger girl stood up and wrapped her arms around both of us as much as she could. She looked up and with tears in her eyes and said, "You're the first man to be nice to me in a long time. I want to stay with you too." We stayed in the 'group hug' position for a few more moments and then broke up without looking each other in the eye only to sit awkwardly around the bed, not looking at each other.

I motioned to Jennifer that I wanted her to make the first move. Never one to be subtle, she sat down beside Chloe and pulled her down to the bed as they began kissing. In a moment, Jennifer was straddling her and Chloe was on her back. I got behind them and lifted Jennifer's robe to reveal her perfect ass. As my hand began to fall against it, I heard her moan into Chloe's mouth. I spanked harder and harder until her ass was covered with blotchy red hand prints and she was moaning and writhing uncontrollably. Chloe's robe had fallen open and I could clearly see the wetness of her slit. She was obviously excited by the scene and the way in which Jennifer was responding to the spanking. With Jennifer's legs on each side of Chloe's hips, I had plenty of access to her pussy and ass. I took full advantage, rubbing her slit with my thumb and teasing her holes with my fingers. Eventually, I flattened my tongue and placed it at the top of her crack. She shuddered and moaned as she sucked on Chloe's little pierced nipples. I pushed my tongue down over her asshole, between her inner labia and circled her clit. As I did this, I reached between Chloe's legs and felt her wetness.

When I felt how hot and slick the little blond had become, I was driven wild with a desire to taste her. I nudged Jennifer out of the way and she swung around so that they could alternate kissing and sucking on each other's tits. I hooked Chloe's legs over my biceps and began licking in earnest. She had prominent outer lips and nearly non-existent inner ones. She was all hot, pink and wet with few folds and little complexity. I teased her tiny clit and sucked it into my mouth, scrubbing it with my flattened tongue. I worked it pretty hard for about fifteen minutes before she started to twist her hips, attempting to avoid the ministrations of my relentless tongue and yet get more of it at the same time. I worked two fingers into her tight, slick hole and I began forcefully thrusting them into her over and over. Each thrust brought her precious release a little closer. I twisted my fingers around and curled them up behind her pubic bone, massaging her G-spot. She bucked harder and I felt her orgasm start deep within her belly, radiating outward like an atomic bomb. I kept up the pressure on the inside of her vagina and sucked on her clit until she clamped my head between her thighs and let out an ear-splitting squeal.

Chloe's orgasm was a long time coming but it left her trembling and weak. She took a while to recover but the girls were soon going at it again. After only a few minutes, Jennifer breathed, "Ohhh God, I'm going to come again."

The two girls rolled into a classic sixty-nine with Chloe on top. She licked the slick folds of her partner with one finger in Jennifer's pussy and one in her ass while the brunette bucked and squirmed beneath her. Chloe was certainly more dominant in bed while Jennifer was more orgasmic. The little blonde withdrew her fingers and lifted her head, looking at me with pure lust in her eyes. When Jennifer caught her breath, she began licking her new friend's soft, pink wetness.

I watched from one of the chairs and stroked my dick as the two girls explored each other. Finally, I stepped in and began spanking Chloe lightly with my open hand. She winced at first, then squealed with pleasure as she ground her pussy into Jennifer's mouth. I stopped before I had even turned her butt pink and slid two fingers into her sopping wet pussy. Jennifer was busy concentrating on Chloe's clit, alternately sucking it into her mouth and flicking it back and forth with her tongue. I pulled my fingers out of the hot little cunt and rubbed them around her anus. Slowly, I let one sink in up to the fist knuckle.

"Oh God, Oh God, please, please," Chloe cried as she bucked against Jennifer's face.

I thought I might be hurting her so I pulled my finger out. That only seemed to drive her further into madness.

"Noooooo, please," she wailed as she frantically reached back and tried to move my hand back to her ass.

Once I realized that she was anal erotic, I really started to tease her.

"What do you really want?" I asked as I drew lazy circles around her anus with my fingertip.

"I want you in my bottom," she said, so softly I almost didn't hear her.

"You want me to fuck you in the ass?" I teased.

"Yes," she meekly replied.

My dick was slick with pre-cum and I pressed it against her little rosebud. She pushed back and the head slipped past her sphincter. I saw her fists ball up the sheets as she accommodated the sudden intrusion. I pulled back to keep from impaling her and to give her a chance to adjust. When I saw her start to relax, I began to slowly push forward. Chloe was too wild with desire to wait and hunched up her shoulders. With all her weight, she shoved back against me, taking every inch of my throbbing member. The feeling of her asshole expanding and sliding down the length of my shaft was almost too much. She was impaled on my dick and I gave her some time to get used to the fullness. After I saw the tension fade from her shoulders, I grabbed her hips and started slowly pulling out. When only the head was left inside, I eased forward again. Chloe pushed back against me and we started a slow but even rhythm. After only a few minutes, something inside her snapped like a spring.

She started slamming her ass back against me and yelled, "God yes, fuck my ass, fuck it, fuck my ass, give it to me, God yes!"

The feeling of my dick filling up her tight little ass and Jennifer underneath us alternately licking my balls and sucking Jennifer's clit was more than we could take. My dick swelled and I shoved it in to the hilt, pumping rope after rope of hot, sticky come into her ass. Jennifer intensified the pressure on Chloe's clit and shoved two fingers into her vagina, driving her over the edge. We collapsed in a sweating, writhing, heaving mass and soon fell asleep, content in each other's arms.

I awoke the next morning to the smell of sex and fresh coffee. The girls were already up and ready for another go. If I was going to survive this road trip, it was going to take a miracle!

To Be Continued...