The Hard Hit

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"Well, now that you are so prettily made up, I want to start with focusing on your face and those red lips." I picked up my camera and aimed it at her and started directing her. "Give me a smile. Good, now tilt your head down and look up at me. Perfect. Head away and up, show me your long neck. Drink your wine and look at me over the edge, now pull your lower lip down a bit with the rim, oh, very sexy."

I remembered seeing some strawberries in the fridge and went to fetch them while Naomi emptied the bottle into her tumbler and sipped her wine. I placed the bowl on the living room table and handed Naomi the biggest strawberry and said, "Here, put this between your lips. Nice. Imagine that you are back on your knees in the bedroom again. That is perfect, oh, I like the tongue-play. Now swallow it."

"Was that good?" Naomi asked.

"Yeah, it looked really hot," I answered, and showed her on the screen.

"Oh, wow! I look sexy, I don't really get that it's me."

"It's the new you. Do you want to see how your body looks?"

"Yeah. Which pose?"

"Let's start with you standing sideways, turning towards me, that way we get your round ass in profile and your pretty face in the same shot. Very good, but arch your back a bit more, good. Sit on that barstool with your legs crossed and hands on your knees, like a pin-up. Shift your dress so the stocking top shows through the slit. Yummy. Sit away from me with your legs the same way, and look to the side, so I get your face in profile. Look sad, look surprised, look at me and smile."

I walked over to Naomi and showed her the new photos, standing closely behind her. Her scent filled my nostrils, flowery and feminine, and I leaned in closer. My lips brushed against her neck and I found myself kissing it, and Naomi moaned and turned her head towards me and suddenly we were kissing. Making out like that, with her sitting and me stooped over from behind, didn't really work. I quickly put down my camera on the counter as she swiveled on the barstool and stood up, and then I pulled her in for a deep kiss, one hand on the small of her back, the other around her neck.

Naomi ran her hands up over my back and down again as our tongues danced and explored, and then she grabbed the hem of my long-sleeved dark grey t-shirt and pulled it over my head. I started kissing along her neck and shoulder as I ran my hands along the sides and back of the dress, looking for the zipper. I found it and dragged it down her spine, then I slipped the dress from her shoulders and stepped back to watch her body as it was revealed to me. Fuck, her body was hot! The bustier gave her more of a waist, and at least a hint of tits, and the garters and stockings were so utterly sexy, especially with those dark red heels. Her rock hard, hairless little cock peaked over the edge of the black lace thong, and to my surprise it didn't ruin the image, if anything, it was even hotter.

I stepped in to kiss her again, my hands exploring her bare ass, so smooth and full and round and amazing. Her hands went straight to my belt and then my pants were around by knees. I kicked off my shoes and pulled my pants and boxers off, along with my socks. I grabbed her ass as I kissed her again and ran my hand down her thigh, lifting it up to my hip. I broke the kiss and said, "Let's take this to the bedroom." Naomi nodded and wrapped her arms around my neck, and as I lifted her by the hips she wrapped her legs around my waist and I carried her, kissing, into the bedroom.

We fell into the center of the bed and I ground my hard cock against her crotch as we kissed. I kissed my way down her neck, over her clavicle and down to her left nipple and licked and sucked it gently. Naomi moaned and arched her back, and I gave her nipple a little nibble, making her gasp. I gave her another hard kiss and then sat back on my knees. I ran my hands along her sides and grabbed hold of her panties and pulled them down as Naomi raised her hips. She had even had the foresight to put them on outside the garters. I pulled the panties over her feet and removed the heels at the same time; a girl accidentally stabbed me with her stilettos once and I've been very wary of heels in the bed ever since.

I kissed and licked my way down her stocking-clad legs until I reached her soft, smooth inner thigh, and then I pushed her legs up and apart. I surprised us both when I let my tongue drag from her balls and up to the head of her penis. The thought of cock had never attracted me before, but her little cocklette looked cute and strangely delectable. I wrapped my lips around the head and sucked and licked like I would a clit, I realized I didn't mind the taste at all, and the moans and gasps from Naomi was reward enough. I licked my way down again and sucked her balls into my mouth one at a time, and then licked over her taint and down to my target.

"Ahh, wait...Oh, wow, that's, that's so good!" Naomi moaned above me as I rimmed her. I ran my tongue in circles around the crinkled edge, lapped over the opening, and occasionally I pressed my pointed tongue against the center to see if I could get inside. After maybe five minutes the opening gave way to my tongue and I started fucking it in and out, getting Naomi to relax and tasting that wonderful taste of a clean anus. Her moans got louder above me, and her hips started gyrating to meet my tongue-thrusts. After a while I sat back and pushed my index finger inside instead, making Naomi groan. I told her to focus on relaxing and started rubbing her cock to help while I gently moved my finger in and out. Her ass was incredibly warm and tight and velvety around my finger.

After a while it got easier and her groans turned to moans, so I pulled my finger out and put my middle finger in my mouth to lube it, and then worked both inside. Naomi got a pained look on her face again, but it quickly passed and she started moaning again. Her dark eyes looked up at me with a fierce desire and she said, "I want you inside me!"

I pulled my fingers from her tight hole and she rolled over and opened the bedside drawer and pulled out a bottle of Astroglide. She said, "Lay on your back, David. I want to ride you."

I smiled, nodded and lay back in the middle of the bed, half sitting against the headboard, and she coated my cock with a liberal amount of lube, making it glisten in the light from the bedside lamp. Naomi straddled me and leaned down to kiss me as I let my hands glide down over her back and down to her hips. She leaned back, reached down between her legs, grabbed my shaft, positioned the fat head against her tight opening and started pushing down. At first it seemed like it just wouldn't work, and I even saw a single tear roll down her cheek and I was just about to tell her that she didn't have to, she could just blow me instead, but then she took a deep breath and as she let it out her tight pucker gave way and the head popped inside. As I moaned at the incredible tightness she let out a loud gasp and exclaimed, "God, it's so thick!"

I reached up and wiped her tear and said, "Just take it slow and let your body adjust. Just this feels incredible; there aren't many girls that can take me in their ass. Try gently moving up and down, how does it feel?"

"It feels, oh God, I'm so full, but it doesn't hurt too bad, mmmhh, feels strange and kind of good. I think I can handle more." With that she started to take more and more with each downwards movement, maybe a quarter inch at a time. Her velvety tunnel felt so amazing that I had to restrain myself from thrusting up inside her. Finally her butt made contact with my thighs and she let out a satisfied moan. She sat there slowly moving her hips as she adjusted to my entire length and then slowly raised herself until my thick head caught on the rim, and then pushed down again, faster this time.

I ran my hands down her body to her hips and started meeting her thrusts with my own, dictating the pace a bit more. The pace increased more and more, as did her throaty moans, and she started squeezing down on me on the upstrokes, making it feel even better. After a few minutes she leaned down and kissed me hard, and then whispered in my ear, "I want you to fuck me hard." Just hearing her whisper that almost made me cum, and after a few more thrusts I rolled us over and pulled out.

I moved her so that she was on her left side and straddled lower leg and placed the other on my shoulder. I have used this position before and know that I can get really deep and powerful thrusts without breaking the intimacy. I quickly added some more lube to my cock and her slightly gaping ass and thrust inside. I didn't take it slow this time, I just fed my cock into her until I was as deep as possible and then started pounding her.

I never knew sex with someone who was technically a guy could be this good, but it was such a fucking rush, and she was so sexy and beautiful, and she really seemed to love what I did to her, and that made this the best I've ever had. I felt myself getting close so I exclaimed, "Naomi, get ready, I'm so fucking close!"

"Yes, fill me with your seed! I gonna cum too! Fuck me, fuck me, fuck me, FUUUUUUUCK!"

As she came without anything even touching her cock, her ass clamped down on my cock and pushed me over the edge. I pushed in as deep as possible and pumped jet after jet of thick cum deep into her bowels as I let out a loud growl. It was a long time since I came two times in one night and I was a bit amazed at how much I still had in me.

After a few deep, ragged breaths I pulled out and laid down on the bed to catch my breath. Naomi rolled over onto her stomach and we just looked at each other for a while.

"Wow, that was amazing, I never knew sex could feel that good, it was like a completely different orgasm!" Naomi said.

"I've never cummed that hard before either, your ass felt so good, and there is just something about you that turns me on so much." I leaned over and gave her a kiss on the forehead and laid back again.

"I don't know if I can go back to regular sex again, I already miss you inside me, I feel empty."

I laid quiet for a while and then said, "Well, maybe you don't have to. You could come with me, be my live in girlfriend. You need to go into hiding, and what better way than changing city and gender?"

"Really? You would want that? Even though I'm a guy?"

"Well, yeah, you're hot, we have great sexual chemistry, and you need someplace to hide. How about this; you stay with me as Naomi, we have some fun, I get you a new identity, and if we get along you can stay as long as you want, if not you have the five grand I promised and you can head out on your own with your new identity."

"That sounds pretty amazing actually. Where do you live?"

I smiled broadly and answered, "Just outside of San Francisco, so even if you get found out, it won't be a big deal."

"Oh, I love it there."

We talked a while longer, and then I jumped in the shower to wash off the sex funk. Naomi got in after me and while she got clean I went around the house and removed any evidence of my presence and I sent a report to my employers about the recovered money and the success of the mission. When she got out she picked out some more anonymous clothes; a flowery summer dress and leggings, and put on just a bit of makeup. She packed a duffle bag with Amber's clothes and we headed out to my rental car. We drove out to LAX where my own car was parked under an assumed name, and switched to that. It is my baby, a BMW M5, a sleek blue sedan with the power and handling of a supercar, and it gleamed in the rising sun.

As I drove up the interstate at about 120 MPH or so Naomi fell asleep against my shoulder, and it just felt so comfortable, like we were a couple in love on a long road trip. It was a nice thought, and I wondered if our relationship, strange as it was, would become something more. I liked what I already knew of Naomi, and she seemed to like me, despite fearing me a bit, so maybe it could work.

Three and a half hours later we were approaching the Golden gate and I shook her awake so she could witness its beauty in the morning sun. We crossed the bridge in silence, looking at the gleaming ocean, the boats in the bay and the city behind us. I deftly navigated through the morning traffic to my little house in Sausalito and we stepped out and stretched the stiffness the road had left in us out of our bodies. I was pretty damn tired so after a quick tour of the house I stripped naked and climbed into bed. I was almost asleep when Naomi climbed in beside me dressed in a silky nighty. I spooned her and buried my nose in her hair, I noticed that she had taken off the wig, but I didn't mind, her hair still smelled feminine and was soft against my face and I fell asleep holding her.

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Mr_OwlowMr_Owlowover 9 years agoAuthor
Chapter 2 is up

I just posted the second chapter, it's a bit shorter than this one, but hopefully it's enough to satisfy.

AnonymousAnonymousover 9 years ago
Great job

Really liked it but continue the story what's next

Mr_OwlowMr_Owlowabout 10 years agoAuthor
Thank you!

Thank you all so much for the wonderful feedback and comments. I was reading the novels about Keller, by Lawrence Block, and decided to combine that with my little transsexual/transformation fascination, and I'm very happy with how it came out and the reception. I wasn't really planning on writing more on this but I think I will, I like the characters and I would also like to see what happens with them. I have a few other storylines going: The Chalice of Change, Finding Himself in Her and Reborn, so this may take a while before it gets the continuation it deserves.

AnonymousAnonymousabout 10 years ago
Continue The Story

I agree with many of the other comments. The chapter is both sexy and romantic.If you wanted it could serve as the foundation for a much longer work. I am sure many of your readers would like to see how David and Naomi's relationship evolves. Suppose David's employers find out who his new companion really is. How far would he go to protect him/her? I certainly would like to know.

AnonymousAnonymousabout 10 years ago
More please.

Oh my, so good. Please more. Romantic, sexy, hot. Lost the connection while reading, and almost cried when I couldn't get back to finish. Please, please, please, write more.

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