Chance Encounter

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A chance meeting takes Tom Rider down a whole new path.
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ShelbyDawn57
ShelbyDawn57
1,385 Followers

I had checked in and dropped my things off in my room at the hotel hosting the computer security conference I was attending; a full week of the latest and greatest in protecting my online customers from things like hacking and phishing. Something my small company desperately needed and did not have.

It had been a very long day of travel and I was entering the bar to destress when I paused to hold the door for a tall, beautiful woman. She had to be 6" tall and wore her height with a confidence that said she had fought for every inch. Her hair was a dark auburn and when she turned to thank me, I saw brilliant blue eyes and a kind inviting smile that led me to ask if she was alone and might like to join me.

She nodded and said she was, and she would. We had an immediate chemistry and after talking over drinks for a few hours about everything and nothing; feeling the chemistry turn into electricity, she invited me up to her room.

We finished the last of our drinks and made our way quickly to the elevator her hand pushing the call button over and over in quick succession trying to make the elevator hurry up.

When the elevator door opened, she pushed me inside with an anxious laugh. Following me into the empty elevator, she selected the button for her floor and turned to face me, moving closer until our bodies touched. I could see the hunger in her crystal blue eyes; raw and primal, like that of a tiger on the hunt. Her breasts stretched the fabric of her dress and caressed the front of my shirt.

As her eyes studied my face, her hands slid up my arms to my shoulders and wrapping around my neck. She pulled me closer, closing her eyes and kissing me passionately. My hands slid around her waist, one going up her back to her shoulders pulling her even closer, the other sliding down to her firm ass, squeezing gently. She moaned softly in approval.

The ding of the elevator and the sound of the door opening and a polite 'Ahem' from the gentleman who was waiting to enter broke the trance and we ran off the elevator toward her room hand in hand like two kids in high school, laughing as we went.

Her room was down the hall and around the first corner. She unlocked the door and once again, pushed me inside, this time more aggressively. Once inside with the door closed, she pinned me against the wall and got on her knees clawing frantically at my zipper, reaching inside my pants, pulling out my throbbing erection.

Her eyes were dancing as she looked up at me and licked her lips. Her tongue reached out and gently twirled around the tip of my cock. It was met by the first drops of precum which she eagerly accepted. Her lips closed around my swollen head as I leaned back against the wall and closed my eyes.

She proceeded to give me the most incredible blow job I have ever had. When she was sure I was completely drained, she gently placed my cock back in my pants. As she stood up, I could feel that something had changed.

She then apologized and said she was taking advantage of me and she just couldn't do it.

I didn't understand, I was a fully willing participant in everything that was happening.

She said that she truly liked me, 'liked me' liked me and that she wanted to pleasure me in ways I could not imagine. The unspoken 'but' in her comment filled the room.

Still confused, I said I really liked her too and I loved what she had done for me and that I would like to pleasure her as well.

Looking away, she said, it might be better to show me and asked me to unzip her dress. She turned around and I hungrily obliged. Her dress fell to the floor exposing an exquisite body, toned and muscular but still soft, her bra and panties were lace trimmed with her panties cutting across the full cheeks of the perfect ass I had fondled on the elevator.

She wore a garter with stockings that made her long legs even more sensuous. When she stepped out of the pool of fabric on the floor where her dress had landed and turned around, I saw the most amazing 8" cock I had ever seen sticking out from her panties.

I had seen plenty of men naked. It's just part of playing sports in high school and college but I had never actually 'looked' at a cock before. I had even jerked off with a few friends a couple of times, but it was more of a competition to see who could cum first that it was anything sexual.

Her penis was perfect, A slight upward curve with prominent veining up and down the shaft and a nice mushroom head. She was shaved clean. Her testicles were huge with one slightly higher than the other. She had been circumcised but I don't think it would have mattered. I was impressed, and surprisingly intrigued.

When my eyes met hers, there was a profound look of sadness there; I guess she thought I would be disgusted. I wasn't sure what I felt but could sense her fear and pain and knew I had to do something to allay them.

Without thinking, I reached out and took her hands and pulled her close enough to me to kiss her focusing on the beautiful blue eyes now brimming with tears. My head was swimming as I kissed her lips gently and assured her that it was ok.

"I was worried you would be grossed out." She whispered softly, averting her eyes from mine. "That you would think..."

"I'm not sure what I think just yet, except that I really like you and want to be with you. I guess we can figure the rest out as we go." I assured her as I placed her face in my hands, gently pulling her lips to mine, kissing her deeply. Our tongues danced in each other's mouths as the electricity returned.

My hands began to explore her body, relishing the softness of her skin and the hardness of the muscles just underneath. I removed her bra exposing two perfect breasts, nipples erect with pending pleasure.

My kiss moved from her mouth to her neck where a few quick nibbles brought out a high-pitched squeal followed by a laugh. "Behave yourself." She said coyly.

I continued down her collar bone tracing a line with my tongue to the valley between her breasts sensing her breathing getting deeper and deeper as I took her nipples, first one, then the other, in my mouth, suckling softly as she began to moan.

My right hand slid down her abdomen to her crotch. Finding her erection in full force, I slid my hand over the smooth skin of her cock finding that I enjoyed touching hers as much as I enjoyed touching my own. My hand slid down her shaft to fondle her balls which were warm to my touch.

I could feel my own cock coming back to life joined by an arousal I had never experienced before. All I knew was that whatever this was, I wanted more, no, all of it.

I dropped to my knees and began suck her cock.

It was my first time and I had no idea what I was doing but tried to emulate what she had done for me just a few minutes before. My focus became letting her know all I wanted was her pleasure. I took her in my mouth as far as I could, and she let out a soft moan like the one on the elevator when I squeezed her ass.

I smiled to myself, "OK, I got this." I took her out of my mouth and twirled my tongue around the tip of her cock looking up at her at the same time. Her eyes were still teary, but the fear and pain had been replaced with something else. I wasn't sure what but looked forward to finding out.

As I turned my attention back to her cock, I was greeted by a glistening flow of precum filling the crease along the bottom of her glans. Using the tip of my tongue, I licked the sticky liquid from her cock and enjoyed my first taste of what was to come (pun intended here).

I lost myself in her cock; sucking then licking then kissing and stroking. I was caught by surprise when she came in my mouth, as much by the act as by the volume. It was almost too much, but I liked the warmth and the taste of her cum, so I swallowed and continued sucking for a little longer hoping for just a few more drops and enjoying the feeling of her in my mouth.

I stood up and pulled her to me kissing her passionately and receiving the same in return.

We undressed and as we moved to the bed. Laying together, we kissed and fondled each other, exploring and touching and caressing every nook and cranny, every intimate place we could find and inventing a few along the way.

She pushed me onto my back and began kissing my chest, biting softly at my nipples and moving her soft hands across my stomach. She slowly moved down my body, stopping to explore my navel with her tongue and sending a shudder through my body in the process.

Her hand had found my erection and had begun fondling my cock and balls as she continued kissing and caressing her way down my abdomen. I moaned as she kissed the tip of my cock and slid her tongue along the shaft moving slowly down to my balls, taking each one in turn into her mouth and applying a soft sucking pressure. I was in heaven.

She gently kissed my balls, each in turn and slid her moist lips along my cock twirling her tongue around the head stopping only to glance up at me and smile before she took me balls-deep down her throat, holding me there as she slid her hand around my ass to my lower back, drawing a single finger along the crack of my ass.

I spread my legs to give her access, allowing her to pause at my anus and gently massage it before she thrust her finger inside me. I'm pretty sure I said, "Oh, Fuck." But I was so wrapped up in all the different, new and wonderful feelings coursing through my body I couldn't be sure of anything.

She slid my cock out of her mouth and smiled at me, "So, you like that." It was more of a statement than a question. I groaned something almost intelligible in response.

Her finger slid out of my ass and she dribbled a stream of saliva onto her fingers, returning to my hole and using the saliva as lube, she pressed first one then two fingers into me curling them slightly forward and rubbing my prostate gently from the inside.

Her left hand gripped the base of my cock, thwarting an explosion as she again started sucking and caressing my rock-hard shaft. The combination of what her mouth and fingers were doing to me was more than I could handle and I'm pretty sure I screamed when I erupted down her throat.

I opened my eyes to see her beautiful smile glowing down at me. Her fingers were still in my ass moving slowly in and out. She added more saliva and then a third finger. "You do like that, don't you? Do you want more?"

"Uh, huh" was all I could manage as she slid her fingers out of my now aching hole. I was lost in a whole new world of unknown pleasures, each new experience more intense than the one that came before it.

I laid there naked as she retrieved a bottle of lube from her suitcase. She looked at me coyly and then at the lube. I nodded my approval and turned over offering her my virginity.

Her soft hands found my hips and moving first up my back and then softly across my butt checks exploring as she went, reaching under and gently squeezing my balls and then drawing a single finger along my crack pausing ever so slightly as she crossed my hole.

Her finger returned, this time with lube and began to caress my anus gently spreading the lube around the outside of my hole. After a few seconds, she pressed the tip of her finger into my ass and slowly inserted it all the way inside finding and, once again, gently pressing against my prostate. It was my turn to moan.

She pulled her finger out and continued to play with my ass adding more lube and moving her finger into me once again. Then two fingers and then three, slowly expanding the opening preparing me for bigger and better things. I couldn't believe what was happening; what I was doing; what I was letting be done to me.

I had never done anything like this before but, for some reason, with her, felt as if it were the most natural thing in the world. She pressed the tip of her cock against my ass and slowly pushed in, just the head, pausing to ask if I was OK.

I answered that I was more than OK and really wanted her to continue. She was soon balls-deep inside me and I was loving every inch of it. It was amazing. She grabbed my hips and thrust as deep as she could as she came inside me.

I had never experienced anything so intense and so pleasurable. As she pulled out of me, I rolled over on my back unable to suppress the smile on my face and noticing the look of contentment on hers. She kissed me gently and thanked me, her eyes no longer full of tears; the fear and pain replaced by gratitude and compassion.

We climbed under the covers and she nestled into the crook of my shoulder under my arm laying her head on my chest, her hand resting over my heart, and her leg across mine. I wrapped my arm around her pulling her even closer, kissed her softly on her forehead and laid back and closed my eyes, reliving every moment of what had happened in my mind and wondering what was next. My smile never faded as we fell asleep in each other's embrace.

I woke up the next morning to her laying on her side, up on one elbow, sucking my cock. I followed the lines of her body from her face to her shoulder, past her perfect breasts, down her waist and hip to find her legs open and her cock next to my face.

I rolled toward her and took it into my mouth. We sucked each other until we came in unison. She turned around and brought her face to mine kissing me deeply. I could taste my own cum on her kiss; kissing her deeply in return as I tried to get more of the wonderful taste from her mouth.

After a long embrace, we got up and showered together.

She washed me, and I washed her. We rubbed our soapy bodies against each other and I could feel her getting hard again against my stomach. My body was reacting in kind. I reached down and started stroking her cock. She stepped back and put her hands on my arms gently turning me around.

I knew immediately what she had in mind and eagerly bent over. Her soapy cock found its way inside me and she began fucking me; slowly at first and then harder and harder; reaching her hand around to fondle my cock as she thrust inside me. She went deeper and deeper until I could feel her balls against my own.

I moaned in pleasure as my own cock exploded onto her fingers and the floor of the shower. She raised her hand to my mouth and I licked and sucked the cum from her fingers. I was in heaven.

One last thrust and I could feel the pulsing of her cock as she came deep inside me. She held her cock inside me for a few minutes wrapping her arms tightly around me pressing her breasts into my back as if she were afraid, I would get away. Like I would even try to at this point. There was nowhere else in the universe I wanted to be than right there in that moment with her inside me.

We finished our shower and dried each other off. I picked my clothes up from the floor and got dressed. I watched intrigued, as she meticulously selected clean things from her suitcase. Her body was athletic and while not overly feminine, decidedly beautiful.

She had a nice tight butt with a thin waste with a muscular back, perhaps a swimmer. Her breasts were perfect, not too big and not too small. She was in all a naturally very attractive woman with a very nice cock. She caught me looking and smiled at me.

I blew her a kiss and smiled my approval for what I was seeing. She blushed in response, letting me know that she like that I liked, well you know...

I was amazed at how her manhood disappeared into a world of femininity; lace and satin, softness and beauty as she got dressed, awed as she put on her makeup, fixed her hair and once again became the beautiful woman I had met the night before.

We went to the elevator and I told her I would like to meet her in the restaurant for breakfast if she was interested. Her smile melted what was left of my hesitation as her hand found mine and she agreed. She kissed me sweetly when the elevator stopped on my floor reminding me to hurry as I went to my room to change.

We chatted innocently about nothing over breakfast trying to not think about the fact we might never see each other again and holding tight to the wonderful memories we had made together. My mind was reeling in thoughts of the door she had opened in my life and what I was going to do about my new-found passion.

As we got up to leave, she pulled a lanyard out of her purse for a week-long computer security conference. I started laughing. She asked what was so funny, a look of hurt and confusion on her face. Her laughter matched mine as I pulled an identical lanyard from my briefcase.

"By the way. My name's Casey. Casey Dearing." She said as she put her hand out to shake mine. Her crystal blue eyes danced as I took her hand in mine. "Tom. Tom Rider, Nice to meet you." I said.

It was going to be a very good conference.

ShelbyDawn57
ShelbyDawn57
1,385 Followers
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9 Comments
smoothed273smoothed273less than a minute ago

👍👍👍💖💖💖💖💖💋💋💋💋💋💋💋✌🙏

manhassomanhassoabout 1 year ago

Nice and endearing story.

smoothed273smoothed273over 2 years ago

The cock size doesn`t matter as it`s the cock size that matters to You.

suckermansuckermanabout 4 years ago
great tory

First please write episode 2. That in itself shows I really liked it. my one complaint would be the usual massive 8" cock, I know its only a story but having several friends in the tranny and sissy community the largest is just a bit over 6" the smallest just under 4", mine . A girl with a cock is always beautiful but a girl with a smaller cock is even more so. Just my own opinion. I will read the next instalment even if its a 9" cock. lol

EnjoyBothEnjoyBothabout 5 years ago
You Have a Knack for This

You have a knack for this storyline. Very well done. Wonderfully erotic.

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