Rex

Moving to the couch with our martini’s, Sammy slips back into old habits. “You look good in a yacht,” she says clinking her glass against mine. “I’ll bet you could get used to this lifestyle.”

“Actually, I’ve always envisioned myself as someone who went out and made things happen for myself,” I reply, wanting her to understand that all guys aren’t leeches. “I always thought it would be as a professional quarterback, but now it will obviously be something quite different. I’ve never aspired to being a kept man if that’s what you are thinking.”

“No, it just seems like you would be a natural with lots of money,” she clarifies. “You’ve got the wit and charm to pull it off. Most guys our age have no clue how to treat a woman or people in general. They get a little money and become total assholes.”

“I guess I’ve never equated money with someone’s worth as a person. I know rich people who are very down to earth and I know others who I can’t stand to be in the same room with.” I look into her eyes. “I think it comes down to who they were before they got rich and how they got it. Trust fund babies tend to be a lot more arrogant than those who earned it.”

“So you think I’m arrogant?” she snaps, taking immediate offense to my comment.

“No. I like you. But not because of who your dad is or how much money you have.” I slip my hand along the side of her jaw and smile into her untrusting eyes. “You have to realize that you’re an awesome woman. You’re beautiful, we had a lot of fun at dinner and I find you incredibly sexy.” I actually feel a rise in my pant leg just talking about it.

“You think I’m sexy? Why?” she asks almost suspiciously.

“Are you kidding? You’re a total package. How many women look like you and have a big enough heart to spend their youth taking care of their mother?” I ask, still wondering why it was left up to her. Her father could afford to have an entire nursing staff if he wanted.

“Well, that’s what Dad wanted,” she says with a sigh. “He didn’t want strangers taking care of her.” Her eyes turn to the floor once again. “That still doesn’t explain why I’m sexy,” she grumbles.

“To me, being sexy is more than just your physical appearance. It’s your smile, the way your eyes light up when you talk about something you love, the way that you giggle when you’re nervous and how you latched onto my hand when I confronted your ex-boyfriend,” I explain, setting down the martini and moving closer to her. “You have to realize that there are lots of guys out there who would kill for a woman like you. That smile of yours is worth more than all of your wealth.”

“My mom wouldn’t let me wear makeup until I was sixteen,” she says with obvious residual bitterness. “Who would do that to someone with this pale skin and freckles? In the summer when everyone else got tan, my freckles would all bloom. I never felt pretty compared to my friends. My friends are all gorgeous.”

“I had freckles every summer when I was a kid, but I don’t have many of them anymore.” I had a serious patch of them across both cheeks and my nose every summer back then, but I haven’t really thought about them in years. “I think you’ll still be hot, even if your freckles bloom.”

“They aren’t as bad as they used to be since I’ve given up on tanning and use sunscreen everyday. If you’re right about me being pretty, then why do I have so much trouble with guys?” she asks, turning back to the topic at hand. “Things always spiral downhill after the first few dates.”

“You can’t expect to tell them your father is worth billions, show them the mansion you live in and the yacht anchored in the marina without it having any effect,” I reply, wanting her to really think about what she’s doing. “Most guys would kill to gain access to that type of wealth.”

“But not you,” she says, rubbing her hand along my jawline and staring at my lips. “You seem impervious to it.” She leans in and brushes her lips against mine.

“Both of my parents are very successful and I consider them failures at life,” I whisper. “They were never around for my sister or me and they have a pathetic relationship. So I’ve adopted the philosophy that money isn’t everything. I want to be happy and become successful by helping other people find happiness. That’s why this whole sex surrogate thing was kind of intriguing, now that I can’t play ball.”

“Cindy says you have a knack for making women happy,” she says, sliding her hand along my inner thigh. “I think I see why,” she adds as my dick hardens against her hand. “I’ve never had a great sexual experience. It’s always been a letdown afterwards. Then I feel all guilty, because I basically don’t feel anything at all.”

“What do you expect to feel?” I ask out of curiosity.

“It would be nice to feel like I want to do it again or something.” She struggles to put her feelings into words. “It all just feels so empty. Like I’m doing the guy a favor by letting him fuck me or something.”

“Wow! You must be having sex with the wrong guys.” I reach for my martini and take a long sip of it. “So, you’ve never enjoyed it at all?”

“It’s not like it hurts or anything,” she says, scrunching up her face. “I don’t know. It’s just never been a great experience.” She traces her fingertip along the edge of my swollen head causing it to strain more intensely against the fabric.

“Well, if you’re trying to drive me crazy, I think you’re doing a great job.” I try to shift in my seat to relieve a little tension.

“Come here. I want to show you my room.” She giggles before standing up and holding out her hand. “Since I’m an only child, he had them put in two master suites. One of the few benefits of being an only child.” However, the fact that she won’t have to share that inheritance with anyone else has to have crossed her mind. One day, she’ll be one of the wealthiest people in the world. Hopefully she gains some self-confidence between now and then.

“This whole interior is gorgeous,” I tell her as we move down another corridor that’s adorned with rich wood, tastefully blended with modern art and furniture. “This has a lot of windows for a bedroom.”

“They all have power black out shades, but since I’m with a stud like you I think we should leave them open.” She smirks, grabbing me by the belt. “Let them see what I’ve got rocking my boat.” I glance out the window and there isn’t a soul in sight. Besides the windows are heavily tinted, so no one could see in unless we left all the lights on.

“You don’t seem all that frigid to me,” I tell her, slipping my hands around her waist. “Am I just bringing out the naughty in you?”

“You’re my night in shining armor, from what Cindy says. My last hope.” She unbuckles my belt as the naughtiness flashes in her eyes. “You aren’t going to let me down, are you?”

“No. I’m going to give you a night you’ll never forget,” I grab hold of her little dress and lift it over her head before turning her away from me and cupping her breasts from behind. “I’m going to show you how a woman should be loved,” I murmur against the side of her neck, my fingers tracing circles around her nipples.

“Oh my god, you’re already making me wet,” she says, leaning back into me.

“You haven’t seen anything yet,” I reply reaching over to click off the lights before guiding her onto the bed and stripping her of the bra and panties. “I’m going to take my time with you and if you don’t feel anything by the time I’m finished, I may have to reconsider this line of work.”

“I’ve never been with anyone close to your size,” she says with awe in her voice, reaching for my already stiff cock. “You’re going to have to take it easy with me.”

“Maybe in the beginning, but I’m going to have you pleading for mercy by the time I’m done with you,” I whisper, nibbling on her earlobe while continuing to roll her nipples between my forefinger and thumb. “I’m going to start with your clit,” I tell her, letting my hand glide down her midsection while kissing my way to her left breast. “Then I’m going to show you a magic spot that you obviously haven’t discovered yet.” I draw her nipple between my lips and simultaneously begin massaging her clit, moving in slow deliberate circles over it. I can feel her tense up beneath me, but I continue unabated for an extended moment before kissing my way over to her other nipple.

“Oh god,” she moans as soon as I latch onto the second nipple. I instantly know I’ve got her. I increase the intensity while kissing my way back to her parted lips. “You’re a naughty boy,” she says, her hips beginning to squirm beneath my touch. I take her lips with mine, my tongue dancing around hers as I begin to massage the length of her slick heat with my finger tips. Things continue to get hotter as I proceed to explore the sensitive recesses of her body. She seems especially sensitive to me teasing the entire length of her inner lips. I can feel her body tense each time I reach her clit without giving it any more satisfaction. After lingering for several minutes, I finally push a finger inside of her. “I’ve never wanted it like this before,” she admits, kissing me hungrily.

“I think you’ll like this,” I reply, pushing my middle finger a bit further inside, caressing her tender flesh until the telltale bumps appear. Once they become fully prominent, I push just past the bumps to a deeper spot and begin making a come hither motion with the tip of my finger.

“Oh… god…” she whimpers, her eyes popping wide open in the dim light. “I’ve never felt anything like...” She grasps my arm as if she wants me to stop, but makes no effort to actually stop me. “What are you doing to me?”

I prop myself up on an elbow, tasting her lips with my tongue while continuing to titillate her with my finger. I squelch each gasp and moan that emanates from her lips. The combination of teasing and subduing her seems to be something new for her. Her pale skin is becoming increasingly flushed in the dim light, acting like a sexual barometer, telling me that her body is definitely responding to my touch. “Welcome to the joys of sex,” I murmur against her lips, slipping a second finger inside before ravishing her with both fingers.

“Fuck!” she screams, her fingernails biting into my sides as she attempts to escape my grip.

“Shh,” I whisper against her lips, slipping my fingers out of her. “I was just testing your limits.” I can’t help the grin that appears on my lips. “I can’t believe you’ve never been with a guy who knew these things.”

“Yeah,” she gasps, still squirming away from me. “How the hell did you learn that stuff?”

“Psych 202 and experimentation,” I admit, chuckling at her expression. “I can tell you right now, you’re never going to look at men the same way again. You’ll be looking for the confident ones who know how to treat a woman, instead of boys with cute butts.”

“But you have both.” She squirms back down toward me.

“Thanks,” I whisper, repositioning myself between her creamy thighs. “I’m not finished with you yet.” Kneeling between her legs, I pull a condom from the wrapper and roll it on. There’s no sexy way of doing it, but it’s quickly forgotten when I rest my rock hard cock against her moist lips. I begin kissing her with a passion I haven’t felt in months. Part of me realizes that this is a professional service I’m providing for Sammy, but it’s an amazing first session as a sex surrogate.

“Go slow,” she begs as I force the tip inside of her. “I’ve never…” She loses her train of thought as I begin to move my my hips back and forth just slightly. After a moment of warm up, I allow myself to go a bit deeper probing the sensitive area that is still aroused from my fingers. A moan escapes her lips and she once again clenches my sides. I hook one of her legs and force them further apart, giving myself more room to maneuver.

“I love your body,” I tell her, leaning down and drawing her pert little nipple between my lips once again. Her legs immediately begin to tremble, so I keep a steady pace while switching to the other nipple.

“You’re killing me,” she giggles. I smile against her breast, knowing exactly what is coming next. “Oh… God…” she cries out just before I feel the release. This is a moment she’ll never forget. I lean forward, taking her hands in mine and forcing them above her head. “Oh… Fuck!” she screams as I bury myself deep within her. “Oh shit… oh shit…” she pants as I hold it there for several seconds simply flexing my hip muscles.

I lean in, taking her lips in mine as I begin thrusting in a way that I know is too intense for her over-sensitized flesh. With her legs spread wide and her hands pinned above her head, there’s no place for her to go. I continue to kiss her fervently as I give her one long, deep, bottoming out stroke after the next. Her lips vibrate against mine as I continue to pound her in a way that will leave her intoxicated by an overload of endorphins.

After several deep, shuddering orgasms, she seems to be a bit delirious, giggling while I drive myself to the conclusion of our first encounter. At the end of the final stroke, I bury myself deep inside of her and hold her tightly while I go over the edge. “That was amazing,” I whisper in her ear as I release her hands and slip mine behind her head, cradling it. “You have the sweetest little pussy I’ve ever experienced,” I whisper, giving her soft kisses. Usually I have a hard time coming when I’m wearing a condom, but she got me off in record time.

I glance down at the length of her body and suddenly realize how much different she is than Teresa or any of my past girlfriends. I’ve always been the type who went for blondes with hazel eyes. In fact, that was the only type of girl who really caught my attention. Recently though, I’ve been finding a broader range of women attractive. Each woman has her own unique characteristics that make her beautiful. I wasn’t exaggerating when I told Sammy how beautiful she is. Her dark red hair looks great with her blue eyes and pale white skin. Even her freckles are adorable. “I love your nipples too,” I tell her, lowering my head to give her right one one last suck.

“Well, you can suck on them anytime,” she sighs, closing her eyes as if she’s trying to regain her senses. “My god, I thought I was going to have a heart attack. I was seriously starting to think you were trying to kill me.”

“I don’t think it would be very wise to kill off my only paying client.” I laugh out loud at the seriousness of her expression. “I was just trying to make sure you got your money’s worth.”

“I got more than that,” she says, rolling her head to the side and looking down at her body. “That was the craziest experience of my life. Wow. No wonder some people really like sex.” She lets her head drop back onto the bed. “I’ll double your payment if you spend the night. I’d like to do that again, after I recover.”

“Sure. I don’t have anywhere I need to be,” I reply, slipping in along side her and pulling up the covers. “You just let me know when you’re ready.” Amazingly, my dick is still hard. I think about the fact that I’ll earn a cool thousand bucks my first night on the job. This is going to be a pretty sweet gig. I’ll have to make sure she spreads the word among her rich friends.