A Transitional Tale

Sitting up with a shit grin on her face C.C. asked,"Would you please dress for me Jon?" She crawled over and placed her hand on my thigh.

"What? You mean now?" I asked after what she'd just asked and a bit surprised.

"Yes, now Jon, I'd love to play with you as a girl tonight." she said looking me in the eyes, a sultry grin on her face as her hands gripped my thighs a bit harder. "Come on sweetie, it will be fun!" She continued, raising her eyebrows and tilting her head seductively.

I'm a bit tentative as I don't really know what she has in mind so I reply simply, "Alright my dear. How can I resist that look?" as I take a drag off my cigarette. With that she jumps up, claps her hands together giggling as she runs to her bags, quickly grabbing a pink lace bra and panty set, throwing them at me, instructing me to put them on.

"Here, these white thigh high socks should match well too." she says as she throws the socks at me as well.

As I pull the panties up and rearranged myself she smiles and giggles a bit saying, "Wow, you look so sexy in those panties baby. I love your bulge too!"

"Can you stop laughing and help me with damn this bra?" I ask fumbling around.

As I finally orient the damn thing I bring my arms though the shoulder straps. "Sure sweetie, let me fasten you up." She replied giggling as she took the straps of the bra into her hands. As she finished fastening the bra I started putting on the socks. Pulling them up it felt great to feel my legs enveloped. The slight bulge of my thigh skin over the top made me feel so sexy and combined with the sight of my cock wrapped in lacy pink satin I started leaking!

When I was all dressed she looked at me and smiled. "You make such a good-looking girl sweetie. And without much work! "My goodness. You might need to lose the little hair here and there like your legs and feet as well as under your arms but, seriously!" she continued asking, "How do you feel?"

"I feel kinda cold and silly, and you laughing doesn't help, but, at the same time, I'm hard as a rock, I can't lie!" was my honest response as stating the obvious was, well, obvious! "I feel sexy and that makes me hard C.C.. Do you like that it turns me on?" I asked her.

"I love that it turns you on sweetie!" was her rather fast answer. She continued, "I've always wanted to play with a dressed man but have never have had the chance." she said as she sipped on a bottle of water continuing, "Most men that I've been with would never contemplate such a thing and those that might wouldn't look sexy if they did regardless."

"Good!" I say as I take her face gently into my hands, leaning in and kissing her deeply. "I like making you happy C.C.!" I say rolling away towards the door, taking a last drag from my cigarette then snubbing it out in the dirty then zipping up the tent.

Having not contemplated that I'd lifted my panty clad ass into the air, I was soon reminded of the fact as her hand came down on my ass cheek with a crack. As I grabbed my assaulted ass and jumped to turn towards her I yelped, "Ow ah C.C., that hurt!" Then asked, "What the heck?"

"But, did you like it is the better question?" she asked, giggling and again giving me her side-eye, tilted head, I'm so pretty look!

"I kinda did C.C.!" I replied giggling and lifting my ass up slightly towards her still rubbing my reddened flesh.

"I thought you might you bad girl!" she said leaning back and grabbing a bag, continuing as she reached in, "I keep this handy for people like us!" Pulling out a short riding crop with a wide end handing it to me.

"Not tonight babe but I'd be game sometime." I say after slapping my hand with the crop to test it out then leaning in to kiss her soft and gently as I put it down. "Tonight I just want to play under the sheets and get some sleep for the day tomorrow you bad girl. It's already gotta be five - six in the morning." I whisper as we lay down and I nibble on her ear, pulling the blanket up around us.

"Sounds good to me!" She whispers back as she slides down my body and underneath the blanket.

"Oh baby, that's perfect right now!" I coo as she cups my bulge. Feeling her lips mouthing me through the fabric of those panties was divine. Having never experienced such a sensation and loving every minute of it, I was sold on the notion of pantied play right there! As she continued to get me hard through the panties I strained my hips to keep contact with her mouth. "Does that feel good baby?" she asked reaching up and hooking her fingers in the waistband of the panties and pulling down, continuing, "This should feel even better!"

I lifted the covers to peek now real curious. Noticing it would be helpful if I lifted myself to let her slide off my panties I say, "Let me help." as I raised my body she slid my panties off.

"That's so hot!" she said as she took my cock into her mouth. As she sucked my cock her hands wandered to my chest and she started groping at my breasts, pinching my nipples through the bra.

"Bring that tasty pussy of yours here baby. I want you in my mouth, now!" I said practically demanding she mount my face with her succulent pussy.

"Yeah baby, you want my dripping wet pussy?" she said slapping my cockhead.

"Ow ah, yes baby." I replied flinching a bit then continuing, "I want that sweet wet pussy of yours in my face so bad!" With that she gave my cockhead another good smack, lifting herself from the warm confines of the blanket and mounting my face. Feeling cold air now I grab the blanket and throw it over us.

After she orgasmed many times, and, as it was getting hard for me to hold my orgasm back any longer, I tell her, "I want to cum in that yummy poussy of yours!"

"I suppose you've earned that much even though it is our first night together." C.C. replied as she somewhat reluctantly dismounted my face. We began kissing passionately now distinctly recognizing the taste of my precum in and on her mouth. Sensing my passion she begins kissing me with more passion. Again time stops for us as we kiss for I don't know for how long.

Snapped out of my trace by her moist vagina rubbing my leg as she climbs onto me I ask, "Do you have any condoms C.C.?" as I absent-mindedly left mine in my other baggage.

"Don't worry about it baby, we don't need any protection." she mumbled as she kissed my chest. "Tubes are tied and I've only slept with my husband as of late." she continued as she rubbed her pussy up and down my now rock hard cock. Normally I wouldn't have fucked her but for some reason I trusted C.C.. And, let me tell you, we fucked like rabbits that night with her at first riding me, then me riding her doggy, and finally ending with me cumming deep in her from behind with one leg pushed to her chest and the other outstretched. As my back arched I gave out a loud grunt.

Holding onto her thigh tight with both hands my legs started involuntarily shaking. "Oh baby!" she cooed as my orgasm subsided and I collapsed onto her, my chin leaning on her shoulder and our now sweaty bodies slithering together in a blissful embrace as we begin kissing, my hands cupping her face. We rubbed noses then got onto our pillows to get more comfortable. A thought then crossed my mind and I slid under the blanket to clean her up before falling asleep.

As my tongue reached deep into her pussy and my mouth filled with cum she let out a moan. When I finished cleaning her vagina satisfactorily her clitoris the became my focal point, wanting to work her to another orgasm. And cum she did, all over my face! Coming up from under the covers having accomplished my mission I wiped my face and gave her a kiss then rolled over and pushed my ass back into her. She placed one hand on my naked ass cheek and the other hand found its resting place grabbing my boob, well, more or less bra as she rubbed her chest into my back. I smiled as she grabbed me giving a good ass wiggle and a giggle as I pushed my bottom into her and swear I heard a slight giggle from her as we both feel asleep.

Waking up really needing to pee I looked over to see if C.C. was sleeping. As I look its clear she's awake as she looking right at me as she says, "Good morning baby, how are you?"

I give her a quick peck and tell her, "I'm great love but I've got to pee!"

"Me too but you seem all ready to go and I need just a minute." she replied. Looking down to find my cloths I see both the panties I wore last night as well as my boxers. I opted to quick put on the panties as they're so pretty. Much more so than my plain old boxers I remember thinking.

Arranging my junk in the panties then yanking up my pants I then throw on a jacket to mask the fact that I'm still wearing a bra and walk over to my bag. "Alright, I'll be back in a bit." I say zipping my bag up after grabbing my toothbrush and toothpaste. Opening the door of the tent I then duck out.

After going to the bathroom as well as brushing my teeth I come back and a woman's standing at the door of the tent waiting. As I approached with trepidation she looked and smiled saying, "Here dear, have some breakfast tea and a piece of almond kringle." holding out a plated piece of kringle and a saucered teacup continuing, "After last night it sounds like you could use it!"

Accepting the tea and kringle I'm certain I was numerous shades of red but nonetheless replied, "Thank you. I am very much appreciative of this morning treat to help us reinvigorate." With that I turned saying, "Good morning." then ducked back into the tent a bit surprised to find C.C. already inside.

"Oh my god baby, did you happen to hear our conversation?" I ask as I zip the tent.

"Yes." she replied in a timid voice. "I guess we were a bit loud!" I say as I hold out the kringle offering her some.

Lifting the kringle, taking a bite and placing the rest back down she whispers, "I completely forgot where I was at some points last night Jon. I'm so sorry."

"No worries C.C.. It's was fun and totally worth a bit of embarrassment!" I say smiling as I sit down.

"Really? You don't mind people knowing we fucked and were loud about it?" She asked as I handed her the tea.

After finishing my bite of the kringle I replied, "Well, I'd rather it not have been so public but it's not like we can do anything about it now anyway. If people aren't upset but know so be it. We're all adults here and that pales in comparison to some of the things I've seen here!"

"Come here and hold me baby, kiss me." She demanded opening her arms. "Do you mind people watching?" she asked running her hands through my hair as I lay my head in her lap.

"Well, I haven't often had the extra eyes in the room but have enjoyed the few times when they were." I responded looking up at her.

"How would you feel about people seeing you dressed as a girl? How would that make you feel?" She asked looking down with a penetrative stare.

"I'd be really nervous that I would look silly. Like a dude dressed in a pink tutu with his chest hair hanging out or something. On the other hand, if I looked good, like a woman, and people got off on it I'd probably get off on it too." I responded while flirtatiously batting my eyes at her.

"Well, you look pretty damn sexy in that panty and bra set but I've got another outfit I was planning on wearing but have other things I can make work. After thinking about it this outfit has you written all over it babe. Let me get it out. Up!" she said as I lifted my head off her lap for her to slide out. She did then reached into her bag as she asked, "Would you at least try it on for me?" continuing, "If you look good you can wear it out and if you look like a 'hairy man in a pink tutu' we'll let it remain our little secret. Deal?"

"Okay, but if I look silly I'm not going out and would indeed ask that you keep this between us." I say then ask, "Deal?"

"Yes. Deal." she answers pulling out a pair of black elbow length fingerless gloves and placing them on another bag. "Get naked my boy." she demanded and I immediately and without hesitation started undressing. C.C. reached back into this magic goodie bag of hers as she called it now pulling out nude 15 denier thigh high stockings with red seams and floral lace as well as red lace up backs and a big, gorgeous red bow. Placing them alongside the gloves on her bags she reached back into the bag.

"And these." she said giggling and pulling out red floral lace up thong panties and a matching lace up bra with a large bow in back with a small bow between the cups. "Put these on my pretty." she snapped as she collected the garments and handed them to me. Accepting them from her I finished undressing. "Don't put the gloves on now though, we'll put those on last." she said as she walked to her bags trying to find things for me to wear. I started fumbling with the stockings trying to get them on but being unfamiliar with the whole process was fumbling with them and getting frustrated with not being able to align the seam right.

"Wait!" she shouted noticing my struggles and stopping me from putting on the nylons by quickly and rather firmly grasping both my hands holding them still. "You're going to put a run in those before you even get them on." she snapped. "Hang on." she continued now clearly a bit frustrated. I stopped moving and lit up a cigarette while taking the moment to think about all that was going on.

"Here." she said holding out a pair of silk elbow length gloves for me to grab as she said, "Wear these as you're putting them on. You've got to gather up the stocking to put them on, then slide your hands into the nylons to open them up then place your foot inside the stocking and gently pull them up your leg." she said demonstrating with her arms in the nylon with the seem positioned right. "Make sure you get the seam in back too, get your hands all the way to the toes and align the seem just behind your pinky's when you start also aligning the toe seem parallel with your toes like this. See?" she asked looking at me.

"I do." I answer placing the gloves on my hands. I then slide them into the first stocking opening it up with the seems aligned, then slide my foot in pulling up tight and letting the nylon unfurl as I go along. With as snap I finish putting on the first stocking, and, let me tell you, it felt wonderful!

As I slid my other leg into the stocking I looked down and was getting hard. C.C. noticed this too saying, "My, my, what a naughty boy I've found!" as she pulled out a brown leather lace up mini-skirt as well as a brown overbust steel-boned corset with gold eyelets and buckles.

"Finish getting dressed, and quickly!" she demanded snapping me out of it and reaching into another bag while laying the corset and skirt down on her bags. "Then put these on so we don't ruin those nylons." she said handing me a pair of red leather ankle tie heels which had to be three inches at least. Fortunately for me the heels were wide and my guess was that she anticipated being on unpaved ground and brought these particular heels for this exact reason. Lucky me!

"Pretty self-explanatory." she started continuing by saying, "Wrap the tie around your leg forming x's then tie it at the back with a bow once you've gone around about three times nice and tight. Make sure you keep the straps flat too. They'll look much better if you do." she said as I took the heels from her. I stood up and pulled the panties out and away from me to arrange myself then let them snap back into place after centering them well. Once satisfied I sat back down to start slipping into the shoes.

As I slid my foot into the feels I felt so girly and I loved it! Having finished tying up the first shoe I slid my foot into the other as she shouted, "Arms up. Quick." as she slipped a white, fully-shirred maidens blouse over my now raised arms and over my head. Pulling it down and into place she paused to take a look commenting, "You look pretty damn good already my dear!" continuing, "But you're going to look great in this too!" Handing me the leather mini-skirt. She didn't need to tell me what to do. I finished tying up the second shoe then stood up and stepped into the mini-skirt nearly toppling over but managing to stabilize myself.

After pulling the skirt up over my hips, tucking in the shirt, then turning towards her I asked, "Would you tie me up please?"

Humorously and laughing a bit she replied, "I've only known you a day and you're already begging me to tie you up?" "For sure baby, I'd love to tie you up. I mean, help you get dressed!" she continued as she pulled tight on the x's the ties formed so as to tighten things up nice and snug, then again, and yet again. She wasn't gentle either, she pulled really hard on those ties! She completed her work by tying a knot when things were satisfactorily tight and finished things off with a bow, pulling the remaining lengths to carefully align them. "Whalla." she said raising a thumb and two fingers to her mouth and kissing them then raising them into the air as though she were sending the kiss to heaven while saying, "Magnifique!"

"Wow my dear, you look so sexy right now!" she said as she looked at me and I turned around to pose my ass for her a bit. I was surprised by how hard it was to walk the skirt was so tight! "It's time to get you into this now." she said reaching for the corset. Instinctively I raised my arms and she slid the corset down into place, made a few adjustments, then buckled it up tight. "Lay down on your stomach for me Jon." she said as she finished the last buckle. Laying down she climbed on top of me straddling the small of my back.

She then grabbed at the ends of the ties pulling the lacing tight. Maintaining tension on the ties she then went over each x formed by the lacing and pulled it tight working from the outside in, then pulled the ends tight. She did this twice, then the third time she placed her knee into my back and pulled on the ties hard nearly pulling me off the ground then tied them off in a knot and bow just as she had on the skirt. Once satisfied with her adjustments she got up saying, "There." as she walked towards her bags she continued, "Now for a few finishing touches."

Reaching into another of her bags she pulled out a wide red leather choker with a gold buckle and a 1 inch gold ring at the front with matching leash attached. She detached the leash, then handed it to me smiling and asking, "Will you please be my fucktoy baby?"

"I'd love being your fucktoy baby!" I responded smiling back and placing the collar around my neck, buckling it nice and snug.

She stepped back to look at me. "Hum?" She mumbled as she put her finger to her lips clearly thinking. As she looked me up and down you could see the answer had come to her as her eyes went wide and started glistening.

"I've got it!" she shouted as she started taking out a few of the ear bars she had in her ears, which was her "final" touch. She took the gold ear bars and placed them onto me, with one just behind my earlobe and the other clamped at my earlobe. The one at my earlobe had a small gold chain attached which dangled down much as an earing would and looked oh so sexy. She then stepped back to look at her handiwork.

"Well?" I asked continuing, "How do I look babe?" looking over my shoulder at her and placing my hands on my hips while I raised my ass in the air back arched.

"See for yourself." she said as she reached into her bag and pulled out a mirror. It was a bit awkward in the tent and the lighting was rather dim but we managed to set up a mirror leaning against one of her bags then she illuminated me a bit with a flashlight.

As I looked at myself I thought, "Not bad!" As I was admiring myself in this girly gear lifting my ass and arching my back with my hands on the crease of my thighs, knees together, feet apart. I looked stunned as my cock stirred and I became lost in looking at myself.