Rachel - Crossing The Line Part XVI free porn video

Authors Note: Been a while since I've had a chance to pen another adventure of a character I love. Hope you enjoy... Thanks for reading and all the feedback given in the past. Didn't have a chance to work with an editor, so errors - all on me. Sorry it took so long to get this out there. Rachel M. Moore (All right reserved) December 2, 9:05 AM Bzzz, Bzzz, Bzzz, Bzzz... It was the second time I'd hit the snooze alarm and I could feel the dread of the day weighing on me already. I rummaged around in the covers for a cool spot, pulling the warm body pillow closer and hugged it tight. Faded was the glow I'd felt last night with Casey only to be replaced with the dread of seeing my mom in just a couple hours. Truth be told after he kissed me goodbye I felt the dread of this day beginning to weigh on me. I wish I could roll back time... I was not ready to see either of my parents yet - even my traffic accident injured mom, at the house I was raised in since I was three years old. As bad as that sounds, there was just too much going on in my life right now and I didn't have the strength to wage that battle, even with loving parents. How would I even begin to explain my transformation? How do you explain to someone that you were born into the wrong body? That to your core, the shell you were wearing didn't match the person you were inside... And having this conversation with your parents? Please! Might as well lock myself up in the loony bin now - that would be their attitudes. Do I try to meet her as my former self? Wear a baseball hat to hide my feminine hair style now, try to find a pair of men's jeans that would fit - which I didn't have, wear a loose fitting shirt and a jacket to hide budding breasts. Augh! How was I going to do this? On the ride back from the Grand Cayman Krystal had said I should just go as myself, as I am now. Of course even if she couldn't articulate her point in perfect English she probably wasn't missing the mark with how to play it. One thing she said made perfect sense, "If you are as you, then it is confidence not of question by anyone..." I had way more confidence in believing what she was trying to say while riding the high of my sexual conquest with Casey and the little bit of alcohol courage I had ingested last night... Could I pull it off? Augh! December 2, 9:51 AM "OK, cool I'll get things set. I'll tell him you'll be there around 11:30. I'll text you his room number in a minute. You need anything else?" Brad was talking fast again, as if he had a limited amount of time to set up this meeting - which was true given I had to switch my plans for the day. He even said it was a last minute thing and he needed me to be flexible, blah, blah, blah... But damn it, can't you just slow it down and have a conversation with me? "No, I think, it's OK..." "Awesome! Really appreciate this Rach. You sure skipping out on your mom is going to be OK?" No, but the lesser of two evils is meeting some complete stranger over trying to meet my mom as myself and going down that road. I had decided I was going to meet her as myself, who I really was and this call interrupted that process. I'd have to call her and push that introduction - maybe make it tonight, come out to both my mom and dad? I looked at myself in the mirror, steam still at the corners of the mirror from the long hot shower, hair wet, towel wrapped tightly under my arms hiding small bumps on my chest, makeup nearly complete... Haha, not likely I'd come out to both of them, who was I kidding. I let out a slow huff of air, "Anyway could you send some flowers to my mom?" "Absolutely! Good idea, Rach..." Yeah, great idea... I was already dreading the call I had to make to her when this one ended, "You want the address?" "I have it. Oh, and you know you're probably not going to want to do this at your parents place, coming out that is... Your childhood home is home field advantage for them and I'm sure there's plenty of history of you... I mean if you show up as Rachel, that's just going to compound an already tough conversation where emotions will be thrown for a loopy by a different you coming home. I can set up something for you at the Grand Cayman, think about it. Hey, I gotta run. I'll talk to you later. Thanks again Rach..." And I barely got to say "OK..." and "Goodbye..." before the line went dead. I looked at the phone to see if we really had completed the call and then looked blankly at myself in the mirror. What the hell! I set the phone down, picked up a makeup sponge and went to work finishing my makeup. Did me no good now to try and consider the outcome that might have been had I met my mom, but I wasn't happy with Brad at the moment... December 2, 10:36 AM My phone buzzed on the bathroom sink as I was just finishing zipping up the A-line skirt I'd chosen for this meeting. If I were seeing my mom I'd have worn my Broduer suit, but the skirt I'd picked went well with the red silky blouse I had been wanting to wear since buying it last week. I finished up primping and straightening every pleat in the skirt, then stood back to beat myself up with how I looked. All in all I didn't have much to say, though the obvious lack of breast heft, hour glass figure like Krystal, longer legs, thinner arms, and... Yeah, not much I had to critique here... I smiled in the mirror of the sliding closet doors, I'm an idiot sometimes. I did like my hair and makeup today, though I wished my hair was a little longer. Maybe I should get a perm when it's a little longer I thought and ran my fingers through it... I slipped my 3" pumps on and turned to the side - ass looks good, a bit bigger and rounder than a few weeks back, but looking very nice. No gaf-panty or pantyhose lines. OK, this is good... I heard my phone buzz again and headed to the bathroom. Two text messages from Brad, "Nathan Carp, suite 844, 11:30. Nat is a tech geek from San Francisco. Like I said this morning, he's an associate of someone I've worked with for many years and he's been vouched for. Any problems call me. Thanks again." and the second message "You get this?" Yes Brad, I got it! I replied, "Yes! Thank You...", but knew he wouldn't pick up on what a dick he was on the phone earlier. No problems here Brad, just go see a guy who you don't know, but some other guy can vouch for. I felt uneasy about this meet and when I looked at myself closer in the mirror - Augh! I felt a wave of nervous energy begin to swim around my body. What the hell was I doing? I didn't have time for beating myself up anymore, gotta roll... December 2, 11:21 AM The lobby of the Grand Cayman hotel was more crowded that I had seen it, well since the grand opening a week ago. Guess the owners were sitting with happy smiles on their faces given all the money people were plunking down. I bet a million dollars a day moved through this place, maybe more. Focus, Rachel, focus... I made my way to the suite bank of elevators without as much as a glance from anyone and rode alone to the 8th floor. A dull 'bing' chimed as the doors opened and the signage said the suite I was interested in was to the right. The hall was quiet and I could hear my heart thumping in my ears. I had taken a Xanax Krystal had given me before leaving the condo and while it helped, did nothing for my nervously beating heart. When I arrived at the door for 844 I wished there was a mirror, but that would have only started a whole new train of doubts to leave the station. I thought about my mom and how she was fine with me coming by for dinner instead of lunch - my excuse being work. And I thought about Brad knowing my parents address, how did he know... The door opened and a man in his mid-twenties was taken aback. He had an ice bucket in his hand and looked surprised to see me, probably as surprised as I was that he'd opened the door. "Whoa! You startled me, you must be Rachel. Nice to meet you..." he switched the ice bucket between hands and stuck his hand out in greeting. I took his hand and after a brief shake said, "Yes, nice to meet you Nathan..." "Oh, no, Nat please. When I hear Nathan I think my mom wants me to clean my room or something." He was smiling and I smiled back. "Come in, come in. I was just going to get some ice." and he raised the bucket as if to prove his statement to be true. "Can I get you anything?" He was nervous and talking a lot, no, talking fast, nervous energy maybe? "No, if you have water that would be good." I cringed after saying that. What did I say, 'No' I wasn't coming in, but give me water? Augh... Am I feeding off his nervous energy? "There's some in the refrigerator," he turned to point down the hall, "it's to the left there. I'll be right back, gonna get some ice." he said lifting the ice bucket to his chest. "Sure..." about all I could say and I walked in and turned when the door clicked, Nat was gone. Relax, relax, relax I told myself, but that wasn't gonna happen any time soon... I went looking for the refrigerator, which was in a fully functional kitchen. The suite was more like an apartment than hotel room. A counter separated the kitchen from the living room, a bathroom door was open across the hall from the kitchen area - I thought about sneaking in for a peak in a mirror. I looked around the main living room area and noticed a closed door, likely a bedroom just off the living room. A huge balcony with a view of the strip framed the far end of the living room. There was a knock on the door and I spun quickly, a bit of water spilling from the bottle of water I'd taken a small sip from. Did he forget the room key? I walked to the door, opened it, and Nat was smiling back at me, "Yeah, forgot the key," he laughed, "I'm a bit nervous..." I smiled, "Imagine how I feel... I spilled a little water on the carpet." "Don't worry about it..." as he walked to the kitchen and placed the ice bucket on the counter. "So, you having a good day so far?" "I've got the usual stresses, you?" I said feeling like I could just speak my mind for some reason. Hopefully he didn't ask about my stresses. "Good day, couple work issues I had to deal with, but nothing to get too worked up about. I should be off the grid for a bit." "What is it you do?" "I'm a computer guy, so lots of stuff... Do we do the money thing upfront?" he walked over to an end table drawer and pulled out a stack of cash. "This is five-thousand dollars, I can get more from the hotel if necessary.", he held it out toward me. My heart sank and I looked around the room again, the bedroom door was closed, is that where they were? If I said anything about the money would the door open and the room fill with police? I took a step back and looked over my shoulder to the hallway and the door to get out of here. Run, I heard my inner self scream! "Something wrong?" Nat asked... Nat speaking snapped my head back around, "No, but I think maybe I should leave..." "Whoa, whoa... Wait a second, did I spook you? Is it the money? Brad said I could pay him later, but this is like new to me, so I just made sure I had the five-grand on hand in case you were expecting it or something. I'm not a cop if that's what you are thinking." "No, I think I should leave..." and I was staring at the bedroom door. "Wait, wait, wait... This has gotten off to a rocky start", Nat looked toward the bedroom door, "There's no one here - feel free to look around." I took a step back and Nat walked over to the bedroom door, opened it, and waved me over, "Seriously, come see... No adjoining room, just you and me here." His voice was calm and any of that nervous, fidgety energy he had just a few minutes ago was gone. "Look, Nat, I don't... I don't do business things." Oh God that sounded stupid, "I mean, Brad... No, that's not what I mean..." Fuck! I should just turn and walk the hell out of here. "Rachel, I know this might feel odd, but, but here," Nat reached into his wallet and pulled out a business card, "This is who I am. I'm not a cop, this isn't a sting, this, I don't even know what this is yet... But please don't leave." I took the card, Syntheon Technology, Nathan Carp - CEO, and an address in San Francisco. I looked up at him. I tried to remember the text from Brad, he'd said this guy was from San Francisco, right? "I'm Nathan Carp, Nat to my friends. I run a nearly billion dollar cloud based tech company in San Francisco. We've got just over 100 employees, and we do work for some very big industry companies you've certainly heard of... Here, you can look me up...", he turned toward a coffee table and picked up a tablet, touching the screen a few times and finally turning the display toward me showing the company officers, his picture and a short bio was on the screen. He was listed as the CEO / Owner... "Look Nat, I, I'm new to this stuff and..." "I know, I get it, I really do understand...", he interrupted me. "What do you mean you know?", concern in that question obvious in my voice - which I hadn't consciously thought about controlling since first speaking to Nat. Why was that? Nat looked uncomfortable again and took a long moment before replying, "Brad had said you weren't a professional, that's all..." Something about his tone said there was more, "No, there's more to it, tell me now or I'm leaving." Another long pause, "OK, so I do know a little more, but only because I need to know what I'm getting myself into. I've got to protect myself, it's not like I can just go out and not have my actions scrutinized. Things I do can have far reaching effects on my personal life, my business. You have to know that." "Yes, but you think you know me? What the hell?", and now I was beginning to get angry and I'm sure my tone said that loud and clear. "It's not like I know everything about you, but I do know who you are and a few other details. Not like your life history or anything. Christ, there are limits to what I could possibly know. When I was introduced to Brad and told him about wanting to meet someone like you he said he would see what he could arrange. That was over a week ago and I didn't hear back from him until yesterday. He told me a little about you and I was intrigued. But, I wanted to see if I could find out a little about you, I wanted to meet you. No evil or malice motives on my part. I'm not a creeper or stalker..." Was this guy playing with me? "Like what Nathan? What do you think you know about me?" There was a slight sigh, but he rattled off the cliff notes version of my entire life. No pause between details, which were all facts about my life. From the first fake email address I created for exploring LGBT blogs and researching transformations, to things that happened after meeting Brad - including being a patient of Dr. Bill, when my driver's license was issued as Rachel, where I was living currently, the Miata I drove, and even information about Krystal. He even knew where I went to high school, about my parents, and my dog who'd died a few years back. He even said he'd seen a couple pictures of me as my former self! With every fact he tossed out there I could feel my chest getting tighter and tighter. He even explained how he found out some of these things - Thank You Facebook! I need to delete that damn account / profile. Some of what he explained I didn't understand, but it made me feel like I would never use another computer again, EVER! When he was done, we just stared at each other for a long uncomfortable minute in silence. He'd certainly cooled the room and sucked all the air out of this meet... "I only dug to make sure I could be safe with you...", Nat said in a low voice. The way I was feeling, the door out of here was the right choice, just turn and start walking, don't look back. But something was making me curious to know more about how Nat had done this and why, why he would go through so much trouble to know nearly everything about me. It can't be just his security needs. And of course there's the question of what he was doing here to begin with? Everything about being here today was odd. What was the end game? "Are you OK?" No, and what does you having all this information do for my security? "Why,", I mumbled... "Good question. It's more than the security, I'm just attracted to the person I've gotten to know without ever having spoken to her." "You don't know me Nathan..." "And now you know why I'm here." "What does that mean?" He took a moment to formulate his thoughts, "Well, this really isn't how I thought this meeting was going to go, but eventually I'd have wanted to know what's going on inside of your head. You can't get that without interaction..." "And how was this supposed to go Nathan?" Nat looked uncomfortable, but answered with confidence, "I find you amazingly attractive and it would be a lie to say I wouldn't want to possess your body and get to know what makes you tick..." "So, sex and a brain scan?" I said with just a tinge of annoyance. The deck was stacked against me from the get-go. I wanted to blame Brad, but that was probably unreasonable, maybe not... I didn't like the position I was put into by a couple guys who were only after things that benefit themselves. My want to run was slowly turning into wanting to get a little more control of where this meet had gotten away from me in so short a period of time. He chuckled nervously, "Have you looked at yourself in a mirror? You are beautiful and any guy would want to be with you. So, as to your question - Yes and No. If we spent the time just talking I wouldn't chalk it up to wasted time if you promised to see me again, call that your 'brain scan'." I wanted to laugh, managed to suppress that urge, but couldn't help but smile a little. Damn it! I think I like this guy, but why? How do I gain some control? "OK, let's start over..." was all I could come up with. "Do you want to come in from the outside again," he said with a smile. I smiled in return, "No, but let's shake on whatever we say or do or don't do is between us? Is that fair?" I wasn't comfortable yet with the idea Nat knew so much about me, but I was certainly interested in finding out whether he could help me erase my past. Nat step over to me with an extended hand, taking mine, and did a ceremonial type of shake, "Deal..." Nat was a good looking man, no denying that, gorgeous hair, at least six feet tall, and for a computer guy had a hard body that certainly took some work to get and maintain. He probably wasn't super model worthy, but maybe some gold digger model might wanna chase him to a big church marriage ceremony and his bank accounts. I didn't release his hand from our shake and just pulled him along toward the bedroom. He followed, I tossed my clutch on the coach before leaving the living room area. Control time... "We don't have to..." he began, but I stopped and turned to face him at the bedroom doorway, still holding his hand. "Let's not over think things Nathan..." I put a hand to his cheek and pulled him closer for a quick kiss. He tried to further the kiss, but I broke away and continued into the bedroom - him in tow. The curtains were closed, so it was dark, but enough light was sneaking through both the curtains and the bedroom door to make the setting comfortably intimate. At the bed I nodded, and said "Sit..." Nat did and put his hands on my hips, looked into my eyes and said in a low voice, "This is new for me Rachel, I don't know if I can..." "We're not over thinking right now Nathan. You want to know me, let me be me, you be you, we'll be fine..." and I leaned in to kiss him again, this time with a little more effort and passion. His response was immediate and he pulled me close, all while our tongues explored, twisted, and the kiss became more urgent. I could feel his hands move down my hips, then slipping quickly beneath my skirt, eventually finding a firm grip on my ass. To say it wasn't electric or making my knees want to buckle would be a lie. Nat was sexy in the sensual way in which he was kissing me, in the way he went for what he wanted... Slow, but no lack of passion that was urgent and exuded a deep wanting. This may have been new to him with someone like me, but I'm certain many women before me were very well pleased having spent some time with this man. When I broke our kiss, Nat stood and pulled me in to kiss again, moved his lips to my neck and I let out an unconscious moan. I could feel his hands unzip my skirt and with barely a shimmy it fell to the floor. He stopped to allow me to step out of it, reached down and picked it up, putting it nicely over a chair in the corner. When he returned he placed a kiss on my lips gently, then another on my cheek, settling in at my neck - which garnered shiver that ran through my body. I could feel his hands were busy undoing my blouse, but his kisses weren't waning. I felt flush, and tried to reach for his belt, but he whispered in my ear, "Just be you..." I thought I was going to melt hearing that, but a chill when my blouse slid down my shoulders and arms made my skin tingle, come alive, goose bumps covering every exposed inch of skin. I watched Nat put the blouse over the chair, then come back to me. "Shoes..." he said softly, running hands over my pantyhose covered legs, then kneeling to take each off for me. Now he looked very tall, without the added height from my heels Nat appeared to be well over six feet tall. I watched him place my shoes them next to the chair, and take the few steps between us to kiss me again, tongue searching and wanting that return of energy, getting it and wanting more. That kiss moving to my neck, then lower, between my budding breasts, to my abs, belly button, and then his fingers were carefully pulling down my hose. As they came down I stepped back a half step and sat on the edge of the bed. Like the rest of my clothes he put the pantyhose on my other pieces of clothing, returning to me and kneeing before me. He stared a long time into my eyes and it almost got uncomfortable, but he leaned in to kiss me. His hands holding my shoulders gently, then moving slowly to my back and my bra strap. "Wait..." I barely whispered into his ear. "Just be you..." and with so little effort he had the clasp unhooked. I reached up quickly to hold the bra over my barely existent breasts, "Nat..." He took my hands in his while looking into my eyes, "I'm where I want to be, with who I want to be with... I want all of you Rachel." Timidly I released the grip on my bra and let Nat remove it. Not knowing what to do with my hands I cupped my hands over the not yet A-Cup lumps on my chest with large firm nipples that were more sensitive at this moment then they had ever been poking my palms. Nat kissed the backs of my hands, then guided my hands to my lap. He was the first man to see me like this, to break down that mental hang-up with my breasts I was so self conscience about. If he didn't walk away in disgust or burst into laughter it would be a miracle. Again there was a long staring moment, then Nat's hand brushed under my left breast, spreading his fingers to cup me fully, with my nipple sticking out like a tiny beacon. He squeezed gently, then licked over the nipple while pulling it away slightly from my chest. I thought I was going to blackout from the sensations I was swimming against and inhaled loudly, while stiffening. When his other hand took my other breast, I moaned a high pitched, "Ooooh..." and tried to lean into him, quiet my reaction to his touch. That move got me his lips on mine, kissing, tongues sparing, breathes coming loudly through flared nostrils - all while he massaged my breasts firmly and pulled at my nipples. It was as if I were staring into the sun while stars streaked behind tightly closed eyes. I felt like I was hyperventilating when he pulled away from kissing me, only to try in vain to catch my breath when he began sucking on my nipples. I yelped uncontrollably when after sucking the nipple he let it slurp loudly from between pinched lips. I hadn't realized my hands were deep in his hair at this point, holding on while rolling waves of pleasure crashed over me time and time again. "Nat..." I croaked through huffs of air coming faster than I've ever experienced, "I..." and he moved his mouth lower to my stomach, "I..." "Shhhh..." was the reply in a gravelly voice. Nat's hands had move lower also, now at my hips, fingers wrapped in the waistband of my panties, pulling them down legs that dangled over the bed. I wanted to warn him about the gaf holding my little boys clit, but he had it released and panties at my ankles before I could make the words come out. I could feel the coolness of my own juices on my skin and stiffened as he took my clit in his hand. My back arched and a new warmth enveloped my clit and I knew Nat had taken me in his mouth. He was gentle and bobbed his head rhythmically down, then up slowly, down again... No longer could I help but to moan over and over with his every touch, slurp, and tug at my clit. Not only deep and guttural, but loud and primal. My hips rose to meet his face, my toes barely touching the carpet tried in vain to rise my hips... I didn't care how I was moving or sounding, I just wanted to be in his mouth. When a slick finger began to probe my little rose bud I bucked hard into his mouth and felt that feeling of the impending climax click into place. "Na.. Nat..." I huffed reaching for his head, trying to slow him down, but his pushing a finger into my boys pussy was the end and a violent shaking of my whole body made me shriek and twist. I was cumming... "Aaaooh!" I spit out and wiggled in ecstasy as Nat slowed to a stop, releasing my clit, but slowly caressing it with the palm of his hand - causing me to bolt rigid every few passes. "Oh fuck... Oh, God..." I said crossing my hands over my face, shaking my head. The sweat on my body making the room feel cool... Nat, stood and looked down on me, "You OK?" I didn't need to look at his face to know he was smiling ear to ear, "Yeah, I've never... I mean, you know.... A.. amazing..." I finally stammered. "Thanks, I could say the same about you, that really was special for me..." I heard the sound of a zipper, then his belt being undone. I peeked through my arms to see that he was undressing. I was still on a major sensory overload and wondered whether I could do any more, at least without a rest. When his pants hit the floor and this boxer briefs were pulled down the most beautiful cock I'd ever seen was twitching at attention, it would not be denied attention. I thought about sitting up, but was just too tired to wanna sit up, so I scooted higher up on the bed and pulled covers aside to try and warm myself. Nat tossed his shirt on the floor and went over to the bathroom to relieve himself. When he came out he put a couple different bottles on the nightstand, pulled the covers aside, and laid next to me, one leg draped over my mid-section. He was propped up on an elbow looking down at me, smiled, and leaned in for a kiss. It was sensual, slow, and caring. I could taste my juices in his mouth and knew he must have swallowed. When he pulled away he just stared at me with a little smile on his face, one hand tracing slowly around my breasts. "You good?" he asked. I wanted to gush about how amazing that was, how it made me feel whole. I wanted say so many things, but I couldn't engage a single thought into sentences. Tangents went left and right - thoughts rolled over each other. I was still processing how, what I felt, and in the end all I could say was, "Yes..." in a pretty hushed voice. I felt terrible that I couldn't shout how amazing it was, but how would I put... "Good, I'm feeling pretty amazing myself. That was a first for me, so I've got way more I could say if I could just stop feeling like I want more of you..." I reached up and pulled his face to mine and kissed him softly, "I want to feel more of you also..." Nat rolled over and picked up the small bottle with a long nozzle from the nightstand. Rolling back he said, "This is a silicon lube applicator. Not that I'm huge or anything like that, but I don't think pain belongs in the bedroom." I was happy to hear that and he might not think he was huge, but I was certain Nat was about seven inches in size and very thick. I looked up at him, "OK..." There probably wasn't a good way get this stuff where it was most needed, so he just went ahead and gently inserted the tip and squeezed. I couldn't feel the gel, but knew something was now coating my little boys pussy. Nat pulled a condom on and applied some of the lube to the outside. He rolled over and grabbed the second, slightly larger bottle from the nightstand. "This is a heated gel and it's pretty potent stuff..." and without saying anything further put a small amount on my little boys clit and the surrounding area. I didn't feel anything at first, but then a slow warmth spread by the time he had rubbed the liquid in and replaced the bottle. My little boys clit couldn't have been more than the size of his thumb and even fully engorged was thin, less than five inches. The hormones I was taking didn't shrink my clit, but did make it less interested in becoming interested in anything but being in the way most of the time. That Nat was so successful with my little boys clit minutes ago really was a shock. And cumming, that probably was the shock of... Nat leaned in to kiss me, pulled back and said "I will try to be gentle, but you have certainly gotten me worked up Rachel..." I had gotten lost in his kiss and just pulled him closer, he had said my name but I didn't hear what he had said. Nat shifted on top of me when the kissing became more intense. In a single move he parted my legs with his and was comfortably between my legs. A slow pleasing burn around my limp little boys clit was joined by the feel of his stiff cock grinding slowly around and into that area. My hands began caressing his back, moving slowly down to his ass which was moving in slow thrusts over my clit. I grab his ass hard and match his grinding, the warmth at my clit now tingled as we pressed into each other. When I felt his hands slip between us and at my thighs I knew he me in a better position for his cock. I let him lift and spread my legs further apart as he rose slightly on his knees. His cock hung lightly over my little boys clit and slipped slowly back and forth with gentle thrusts. I closed my eyes and tried to absorb everything about this moment, the feelings, the smell of his body, the sounds... His cock brushed over my boys pussy as he gyrated his hips into mine, then ground into my clit. Again he pulled his hips away, brushing the tight rose bud, and rushing over my clit. The burning feeling at my clit had spread to my boys pussy, while his cock pushed and glid effortlessly over pelvic area. We kissed softly, then urgent. I moaned after a few times when he pushed his cock at my pussy rose bud entrance and it slipped up and into / over my clit. I wanted him inside of me and couldn't take this torture any longer. Reaching between us I found his swollen manhood in all its glory with my hands and all motion stopped. We stared at each other as I moved the tip of his cock into place and pulled him slowly to where I wanted him, while he pushed steadily into my tight boys pussy. Even with the lube he had applied it wasn't an easy to take him and I fought how much it was hurting, while trying to relax. My hands now at his waist pushing him away, while I tried to equalize the pressure of his swollen cock stretching my boys pussy. Nat gave into my control of his penetrations and that helped. With each movement of his hips into I had to temper the speed and amount I could take. My clit was burning, so were my balls, and the opening to my little boys pussy. "I can stop... We don't have to do this." Nat whispered. My eyes were closed and was too focused to reply. I pulled his hips slowly down onto me and felt his thighs touching mine for the first time. I let out a tight breath and slowly pushed him away an inch, maybe a little more, then pulled him into me again. It was getting easier to take him in and after a few more guided entries, I released his hips, "I'm... I..." a hard breath of air escaped my lips, "OK, slowly, OK..." Nat was patient and every thrust was slow, every retreat equally slow. After a few more times sliding into me, our hips began to touch with every thrust. When he was fully all the way in he would hold himself in me, then pull nearly out. The pace was becoming quicker now and I wasn't the only one breathing heavily. We kissed, he would grind every inch of his cock into my little boys pussy, then pull nearly out and move a little fast back deep inside of me. Each time he was all the way in it would take my breath away... The bed began to shake more as the thrusts of his cock became stronger, more intense. When the sound of our bodies began making a slapping noise, Nat was in full fuck me mode. Deeply in, nearly pulling out, in, out an inch, slapping hips harder, cock buried deep. I would moan through clinched teeth, Nat would exhale like he was lifting weights. At one point he had pinned my body under his weight and hips moving like a jack-hammer banged his cock repeatedly into me. I couldn't move and the sensations his cock were causing my body to convulse. Breathing was hard and when he didn't response to me calling out his name I resorted to biting his shoulder lightly in an attempt to get his attention. Through huffs he apologized, but jammed himself into me harder I could stand I grabbed his face with my hands, "Nat... wait..." All movement stopped except for each of us breathing as if we'd run up eight flights of stairs to hop into this bed. "Oh... God, sorry about that Rachel, I got carried away." I felt his flex his cock while buried inside of me and tried to shift under him for a more comfortable position. "You OK?" There was still a warmth at my groin area from the gel, but Nat being inside of me didn't necessarily hurt, it just made that whole area down there feel full. "Yeah, can we try something else?" "Oh, yeah. Of course..." and with less care than we started Nat pulled himself from my little boys pussy quicker than I would have liked. Nat rolled to my side and let a hand trace down my body to my clit, then back up to my breasts. It felt amazing... "Your body blows my mind..." I felt flush and put a hand on his chest, "Thanks..." I rolled away from him and backed myself up against his still rock hard cock. Reaching around I took it in my hand and moved it between my ass cheeks. Nat moved his body slightly and lower on the bed, while lifting my left leg slightly. His cock was now poking tentatively at my loosened rose bud and with nearly no effort at all the large mushroom head of his cock was in me. With his right hand on my shoulder and left on my hip he proceeded to pop that chubby head in and fully out of my little boys pussy. It felt absolutely incredible. Sometimes his hips moved the tip in slowly, then out quickly. Sometimes in and out quickly. When he moved his body further up the bed, the range of motion his hips made was more pronounced. That translated to deeper thrusts. His right hand gave up its position holding my shoulder tight to grabbing a hand full of hair. While his new grip hurt a little it was exciting to be controlled like this. He would pump his cock into me so hard and quick our hips slapping sounded like I was being spanked. I couldn't help but moan and moan loudly. The only noise coming from Nat though were heavy breaths. He was in his own zone and would mix up his cocks penetrations into my boys pussy to meet his needs. No mistaking what was happening, Nat was fucking me for his needs and wants alone. It bordered on brutal and I knew I was his bitch, submitting fully, and barely able to maintain any sense of how he was using my body... "Aughhh..." I heard as my head was pulled further back hard and my hand fought to grab his wrist, "Fuck... Oh shit! Rachel... Aaaa... Oh GOD!!" and with a violent shudder that rolled me over onto my stomach, Nat now on top, he thrust twice more and went completely stiff laying on me, grinding into my boys pussy as if he could force me through the mattress or something. His body shuddered fully and I couldn't catch my breath. His muscular legs were crushing in on my own, and his continued want to drive himself deeper made breathing impossible. There was also some serious pain due to the angle of his attack on my little boys pussy. I tried to unpin my right arm from underneath me, to push his body away, but it was no use. My other arm was beginning to ache from him using it to brace himself on top of me, while his pelvis jerking in short forceful thrusts shooting bolts of pain nearly everywhere else on my body. I had felt what was likely the moment he shot his load into the condom, but so strong did his body shake our connected bodies I can only imagine how that had to have felt for him. To say that moment was earth moving would be an understatement, but now I needed air! "Nat... I need to move, you're hurting me..." I said softly through clenched lips. "Ooh crap... I'm so sorry." I could hear him grimace as he tried to shift his body to where he could lay beside me, setting me free. His left knee raising his body quickly off mine unceremoniously had the effect of pulling his cock from inside of me. "Ooow..." I groaned. "Sorry... I... Didn't mean to... You know, move like that." he said with a pleading tone to his voice. "It's Ok... That last bit just hurt a little. I'm fine... I can breathe again." and I giggled a little. Nat laid beside me and I could feel him fidgeting, then the sound of latex snapping broke the momentary silence, followed by him chuckling, "That wasn't so graceful..." "Are you Ok?" "Yeah, I'm just feeling a little awkward." "I'm pretty sure nothing about what we just did was awkward..." and I wondered if I should have said anything. "No... Pretty sure that was incredible for me. I hope... Well, you know, that it was Ok..." I turned into him and looked at him for a long moment, "Really? You're having trouble remembering me whimpering, moaning, all the loud sighs over and over again?" I pulled his face close and kissed him quickly, "That was unbelievably amazing for me Nat. You were more than a generous lover. I can promise you that..." His smile and hug said I'd just made his afternoon. His body was warm and I wasn't opposed to snuggling in closer. It wouldn't take much to drift off to sleep, that's how relaxed I was feeling. December 2nd, 3:44 PM I awoke slowly, feeling the warmth of a pile of blankets on me, and the low hum of an air-conditioner. I was thankful the warmth was from the blankets and not that damn heated gel rub crap Nat applied to my clit area. The room was pretty dark, but the crack in the door to the living room let in enough of a steak of light I could navigate around when I decided to actually move. I rolled my head to the side and caught the alarm clocks digital readout - 3:44. Augh, I need to get moving... I guess one of us dozed off. I could hear Nat in the living room having a conversation with someone, likely on his phone since it was one sided with pauses after he'd speak. I sat up and could feel many dull aches in places I didn't think could ache. Legs dangling over the bed I wiggled my toes and then stood. Ok, my back hurts, I paused before taking a tentative step toward my clothes. Ok, I'm sore but I'll manage... Grabbing everything but my shoes I turned toward the on-suite bathroom, clicked the light on, and cringed at the image in the mirror. Oh boy... I could easily fix the mess starting back at me, I just didn't have everything I needed to do it right. Guess it'll be plan B - heavy blush and lipstick, quick blow dry of the mop on my head, and pray I can slink out of here with as much fanfare as I received coming in. God help me... December 2nd, 4:27 PM I'd just finished buttoning my blouse when a soft tap on the door behind me made me jump a little, followed by "Rachel, you doing alright?" I looked at myself one last time, brushed the front of my skirt for the sixth time and turned to open the door. God I hope he wasn't going to be repulsed at the sight of me... Nat looked me over with a smile, "I think I'd recognize that body, I mean beauty anywhere..." "Haha... " I blurted out and stood on my tippy toes to give him a little kiss. Cute Mr. Nat, very smooth. He wrapped his arms around me and gave me a tight hug, "Guess you need to be going eh?" "Yeah, as much as I would like to stay, I've got something I have to do tonight." "Not another guy? I mean you're not meeting someone else..." He looked very uncomfortable after having stuck his foot in his mouth, "No, actually dinner with my mom. I don't know if my dad will be there..." "Ooh, well that's cool..." "Mmm, not really, but that's a story for another day. Sorry we don't have time for that brain scan." He laughed and followed me into the bedroom, clicking on the lights. I slipped my shoes on, which gave me some of my height back. And asked, "How can I erase myself from being found Nat? I really don't like the thought people could know that much about me now, who I am now..." His face became serious, "You really can't these days. I mean you can make it tougher on those high school kids dicking around the web, but someone with a moderate amount of talent can still find pieces and put together a picture of your life pretty much. Sorry that's probably not the answer you were hoping for." Well that sucks... "Can you help erase some of me out there? Help me make some of who I am invisible?" He came over and took my hand and I followed him to the living room. "I'll see what I can do, but what do I get in return?" and he spun me around as if we were dancing and at the end of the spin wrapped his arms around me, looking down at me for an answer. "What would you like in return?", I said with a raise brow. "Come to San Francisco for the weekend. I have a place in the Napa valley, a small working winery actually, do you like wine?" "Sure..." "I'll send my plane to come get you, meet you there, maybe explore the coast. Can you get away?" "Next weekend?" "Yeah, well unless you don't want to?" I put both hands on his shoulder and pushed back a little, "Seriously? Nat, I don't want to leave now, but I have to. Yes, I would happy to come meet you in Napa." and got on my toes to kiss him again. When we broke the kiss he was all smiles. "Awesome! And if I have to work things out with Brad I can, that's not a problem..." "Brad won't be a problem, I do have free will you know." "I wasn't implying that..." I interrupted him mid-sentence, "Easy big boy, I think I know where you're coming from. Don't over think it." "Ok, cool..." He grabbed my clutch from the couch and handed it to me, "You follow that same advice..." I looked at him questioningly and took the clutch from him, then knew what he meant by his comment. I clicked open the clutch to see the stack of cash from earlier jammed in there. I looked at him, "I'll let Brad know..." "No need, I already paid him. That's for you to buy some things for warm weather when you come visit me...", he was all smiles, "I highly suggest a couple swimsuits." I'd crossed many lines these last couple weeks, maybe today I helped someone cross over one of their own...