Unexpected Attraction

About 2.5 years ago I left a full time, single location site position and switched to this independent contractor job which required me to travel across our medium to large metropolis. In my travels, I would go to this one diner (one of a chain) and it was there that I met this server named Sidney. She had this immediate connection with me that I can't quite explain. Sidney had short hair, a cropped cut and intense blue eyes, crystal blue in fact. Sidney, however, was an enigma to me. I couldn't figure out whether she was a very effeminate young male or a more masculine female. But I did know that when she smiled at me, I'm was truly taken aback. I often thought to myself, how could I be attracted to someone that I wasn't even sure of their gender? But I was attracted to her or him, either way. She always remembered my name and took a personal interest in me each and every time I came into the diner (which is maybe once every 10 days). She did this even if I wasn't at her table. There was this pull there between us like a magnet force. I had even dreamed about her on occasion.

One day while dining, I met her girlfriend...I was still not sure if they were lesbians or not. The uniforms at this diner are not form fitting, so if she had breasts, they were small but then again she wasn't muscular either. A lean frame was the best description. But Sidney also didn't have the obvious masculine curve of the shoulder blending into the arm/bicep or the square of the jaw which is so blatantly male. I watched Sidney and her friend giggle which made me mentally check off the box for lesbian; however, the question still hung there, not really important but ever present. I noticed that I couldn't stop watching her and her friend.

Time passed and I went to that branch of this diner chain a couple of times and she wasn't there. I wondered if she still worked there or had just changed shifts, but I was not going to ask. I mean, I was just a customer; not a friend, not really even an acquaintance. Another branch opened right near my son's school...so it was a perfect location for me because I had to drop him off at 7:10 am and usually didn't have to be at work until 8 or 8:30 at the earliest. Time for breakfast!! Coffee, leisurely eating and precious alone time. The perfect time for writing. I watched the building being built and was strangely excited about the prospect of going. I hadn't seen Sidney for months by then, perhaps 8 months or so. It was possibly even a year and this was a new building so she probably wouldn't be there, I told myself. Could I be just excited about breakfast and my writing time? I didn't think so.

I went on one of the first days of the grand opening...new staff everywhere. I recognized an area manager but no Sidney. Oh well. I routinely went back 1 to 2 times a week because it was so convenient for me. Then one day while I'm engrossed in my writing, I didn't notice someone had come up to my side. This presence wasn't directly facing me like my server would but just beside me, just there. I looked up and saw those blue eyes. But wait, the eyes were different as if someone poured green-grey flecks of paint in them. It was Sidney, but it was not. The shoulders we're broader, the voice huskier when she said hello and...was that a 5 oclock shadow? I smiled warmly and said, "Well hey there. I haven't seen you in forever." She smiled back and said, "I know."

I glanced at her nametag, 'Sid' it said. Sidney is now Sid. It was a subtle difference, but yet no difference at all. She had become a 'he' in those 8 months to a year and had probably had been working towards that change way before then. I knew it was a long process because I had known other acquaintances that had changed with or without surgery. They had compared it to a butterfly's transition. There was tons of work building the cocoon, their surroundings and then the time inside the cocoon itself when they were in between genders until the final surgery burst them forth into their new being, their true self. Even if they chose not to have the surgery, it was still an explosion of sorts into a new self, the self they always knew they were meant to be.

We began talking and obviously flirting. I found myself laughing at the small one liners he threw out. I was thoroughly entranced with him. I'm not sure Sidney even knew what he was doing, but he was making me want him more than in a casual, customer relationship way. My brain was scrambling, trying to figure out some way that I could subtly give him my phone number or email address. Then, I noticed several tattoos on him that somehow I had missed before (or were they even there before?) and I started asking about their symbolism. I did this to try to see if there was some personal connection that I could work with that would then lead to exchanging numbers.

He easily opened up about his ink. Describing one that was personal, having to do with his grandfather and another related to a sports team. But there was nothing there that I could truly grab hold of in order to relate to me somehow. Suddenly he chuckled and said I have others but they're not really appropriate to talk about here. Yes! I almost blurted out loud, that was the connection. It was just what I needed, plus a challenge. I like challenges and told him as much. Sid's eyes just twinkled a bit and then he gave me that easy smile that made my heart melt.

He stepped away from my table for a bit to return to work which gave me time to gather my thoughts and courage. I kept battling with myself about whether I was just making this apparent mutual attraction up or if he was just being friendly...to a customer. I took a deep breath and allowed myself a slow, calming exhale. I closed my eyes for a minute and made up my mind to go for it. Live life in the now, as 'they' say. I opened my eyes and turned slightly to grab a pen from my purse when I literally felt heat on me. Looking up, I saw him staring at me from about 50 feet away and smiling. Had he seen me breathe deeply, obviously shaken, or was he reading my mind?! My hand was grasping the pen but started to shake a bit and I nearly dropped it. Turning, I grabbed a napkin and quickly wrote down my number before losing my nerve.

Ok. Now I needed to give it to him. I waited for what seemed like an eternity but he didn't come by again. All this internal pressure was making me have to pee so I got up to go to the restroom leaving my number on the table in plain site, hoping he would notice it if he came by tHe table. When I was walking back from the restroom , I could see the napkin still laying where I had left it. My heart was dropping with each step I took closer to my seat. I plopped into the bench like seat, a bit depressed when I noticed the napkin in more detail. Written under my number was another set of digits and a quick note stating, "Call me."

My heart jumped and my stomach fluttered. I reflexively squeezed my thighs together, a purely primal response. I could also feel the flush rising up my chest, neck and slowly spreading over my face. Glancing towards him, our eyes met for a brief second but it was enough to say volumes. I started eating the now cool food but immensely enjoying every bite. It tasted so much brighter, richer and vibrant even though it was just typical diner fare. I started to tuck the now neatly folded napkin in my pocket but then quickly changed my mind and subtly placed it into my bra. It rested on my soft rounded flesh; however, despite being as light as a feather, it felt solid and heavy like a hand caressing my breast.

I practically floated out of the diner while daydreaming of all the potential scenarios of how our first meeting might play out. Hurrying through my work day and figuring in my mind when Sidney's shift may end while alloting time for him to get home, change, clean up etc.; I then sat in my living room with phone in hand. I couldn't believe how nervous I was at the prospect of hearing his voice on the other end. Dialing with shaking fingers, I finished the number and waited through three rings before he answered. I stammered out my hello but he didn't seem to notice and easily flowed into a light, social exchange. It wasn't forced or overtly sexual, just like a conversation between long time friends making arrangements to meet up. We decided on a local restaurant that was surprisingly located in an upscale bowling alley.

We met on an ordinary Tuesday night that was slightly cool due to the change in season. I arrived a few minutes early and waited just outside the entrance. I pulled my jacket closer to me, arms crossed due to chill in the air and noticed my nipples were rock hard. I smiled to myself while thinking about how sensitive my nipples are to the slightest touch or temperature change. While my fingers were tucked under my arms, I began to rub myself in tight little circles. This had the desired affect on me by calming my slight anxiety about the heightened anticipation of our upcoming date, but I also started feeling a rising tingle in my sex. A growing wetness building as I stamped my feet and rubbed my thighs together. Then I saw him walking through the parking lot towards me.

As he came up to me, Sidney placed both his hands on my upper arms while rubbing and saying, "You must be freezing, let's go inside before we talk further. " I smiled as I let him guide me towards the door, enjoying the firm direction from him.

Once inside, we walked over to the bar to order some drinks. He knew I liked coffee from all my diner orders so he ordered me an Irish coffee to really warm me up as I was still shivering and then ordered himself a vodka tonic. They bar was surprisingly busy for a Tuesday night so the bartender was behind on filling her orders. Still shivering, I felt his hand slip inside my coat and rest on my hip. Now I was shivering for a different reason. Sidney suggested that we head to the restroom while the bartender was making our drinks. I agreed but even with turning to walk his hand remained firm on my hip, guiding me in the right direction. I felt my heart beat at a more rapid pace. As we near the restrooms that were located down the long hallway towards the kitchen, I noticed that there were surprisingly few people in the corridor. He stopped moving and I looked back at him to see what was up, just as he grabbed my shoulders and firmly pushed me against the wall while leaning in to kiss me.

It was one of the best kisses I had had in years. Just the suddenness of it alone added to its intensity. Sidney just as quickly stopped the kiss as he had started. I was left hanging there kind of disoriented and not knowing what to do. Again guiding me with his hand back on my hip, he directed me towards the women's bathroom and said in a low whisper, "I want your panties. "

I floated in, completed my directed task and still dreamily walked back towards the bar with my pink lacey bikini cut panties balled up in my hand. He was already there, just taking our drinks from the bar and walking towards a small corner table. I slid in and he grabbed my hand, removing the panties and then placing it on his thigh. I looked him directly in the eye and Sidney smirked while his now blue - green eyes brightened. Smiling, I started to rub his thighs in tight small movements while my sex started creaming all over the inside of my skirt. Our eyes didn't shift and the stare was intense just as everything seemed to be with him. His hand started to move up under my skirt as the anticipation grew, I shivered again. Knowing what was coming, I spread my legs wider to accommodate his hand.

Just before he was able to touch my wetness, the server came over to see if we needed anything to eat. Sidney casually broke our gaze, sweetly smiled at her and politely declined. It was so smooth and calm that I didn't come out of my cloud of desire yet when his hand reached the spot. I even jumped a bit thus requiring him to take his free hand and place it on my other thigh. He applied pressure, reassuring pressure that allowed me a moment to gather my nerves. Unconsciously, I must have squeezed my thighs together because he was now using his surprisingly strong hands to separate them for me. Trying to relax on purpose is harder than it seems. However, I was somewhat successful and his fingers began to play me like a musical instrument.

I was far from shivering due to cold any longer but the intensity of his movements on my clit was causing me to quake. He drew small circles with his finger while spreading me open with his others. I was struggling to not moan outloud. Sidney whispered to me to take a sip of my drink, relax and enjoy. But I nearly spilled the hot liquid as I brought it to my mouth. I then felt him move closer to me and I sensed his intensity like a wave of heat from a wood stove. Realizing that I could feel his growing hardness on my thigh, I suddenly became aware that I have a gifted surgeon to thank for that sensation and hopefully more to come.

He was relentless with his pursuit of pleasuring me. Not that I minded of course, but I have always been reserved about public displays. Always worried about getting caught; getting exposed for the inner slut that was screaming to be unleashed. At this point in time, I couldn't seem to hold my head up any longer so I buried it in the crook of his neck and shoulder. I could feel the orgasm starting to rise up in me and I knew I would make noise. This way it might be muffled into him. My hips began to rock counterclockwise to match his movements in reverse but suddenly Sidney stopped.

My head snapped up and I released a soft but audible whine. I noticed him looking across the room with his sensual smirk forming again on his face. I followed his gaze and saw two men talking to each other while staring in our direction. We had been caught. My legs snapped tight together on his hand again, closing his access. But to my surprise he didn't remove his hand or even blink. Instead, he called out our server's name. How did he know her name I thought to myself. How did I miss that? As she walked towards us, I stole a quick glance again at the two men. They were openly grinning and staring back at me, no at us. Sidney said something to her but I didn't make it out because my head started spinning at this point. It must have been a lack of blood flow to my brain so that I couldn't process everything.

The server left and Sid forcefully pushed my thighs apart with his hand again. Damn, how did he get so strong? Wide awake and alert now, he began to cruelly barely touch me. Teasing me and making me want more. Sidney turned to look over at our audience and I followed his line of sight. Our server was handing them the fresh drinks and then they lifted them in a gratitude salute. He had bought them a round as a recognition of knowing that they were watching. But the display it didn't stop there. Sidney turned and looked at me then gave me a deep, long kiss as his finger plunged into me! I could barely catch my breath when he just as quickly stopped and gestured with his head for the two men to join us.

Wait! Did I want this? My mind was saying, 'I'm not sure I signed up for a group situation' but my body betrayed me. My pulse picked up, I became wetter, and I needed to lick my lips...it was all reflexive, spontaneous. The men joined us and at first it was just awkward verbal exchanges but as we drank some more and Sidney kept fingering me, I slowly relaxed. I was able to then submit my whole self and sex to the potential upcoming event. We were in a horseshoe shaped bench at this table so one of the men, Jack he had said, slid to the other side of me. Sandwich-ing me between him and Sidney. Their body heat enveloped me. I felt other hands on my thighs now and I knew that I wouldn't last much longer. I didn't want to orgasm in the restaurant because I didn't trust myself not to get too loud. Turning back towards Sidney, I mouthed, "Not here please."

He immediately understood and asked the other men, Jack and Ben, if they knew of a quieter, less public place we could go. As luck would have it, Ben lived just a few miles from the alley. Hands left me and I suddenly felt empty and cold but still with a quick heartbeat because I knew what was yet to come. I realized then that I wanted it to happen. I needed it to happen.

Sidney and I followed the other two men in his car. He held my hand while he drove. I was strangely quiet so as we pulled into Ben's driveway, Sidney turned to me and gently turned my face to his with two fingers. It was a simple gesture but it really got my attention. He said, "We can leave at anytime and continue on our own if you're not comfortable. Just say the word and we're gone, okay? Also, his voice dropped to a whisper despite still being alone, I may not fully participate. I may just want to watch." I could sense his trepidation, could read it in those beautiful eyes.

I told him I completely understood and was okay for now but would definitely tell him if something changed. He leaned in and kissed me so passionately that I swear my toes curled. We broke our kiss and walked up to Ben and Jack hand in hand, like we had been dating for years or at least months.

We all four settled inside, more drinks were served and some music started from seemingly nowhere. Sidney stood and offered his hand for a dance. So here I was dancing with an audience in a living room. It was a bit surreal but I was lost in his swaying arms. He slowly started to undress me and then I felt more hands gently removing each layer. Ben and Jack took some layers off too but Sidney remained clothed and focused on me. His hands skillfully played me to the point that my knees started to buckle. Jack caught my tumbling body, picked me up and softly reclined me on the couch while bending down as I eagerly opened to take his now exposed cock into my mouth. I felt two hands run up my legs and firmly but not roughly spread them apart.

I jumped as warm wet tongues met my left nipple and clit at the same time. My moan was strangely audible despite my mouth being full. Sidney used his hands, mouth and fingers over my breasts like they never been touched before while Ben artfully licked my sex to nearing orgasm. The men could sense I was near climax as my hips started to grind, I started to suck deeper and my nipples were rock hard. I grabbed Jack's hand and placed it firmly on my head thus signaling to him to push deeper into my mouth. He easily read my signals and grabbed a bunch of hair while plunging down my throat. This sent me over the edge as I spiraled into an intense orgasm and almost immediately started tasting Jack's cum as he shot down my throat.

My hips were still moving on the last throes of my climax as I felt Ben enter me. My hips easily changed rhythm to accommodate this change and moved to his needs as I felt an intense pinch on my nipples that I wasn't expecting but gladly received. It caused me to gasp as Jack left my mouth and I thrust my pelvis deep into Ben. The twisting happened again as I let out a loud moaning yell and thrust again. Ben was matching my movements and sounds now as in a duet. I felt him getting close to climax as he pulled out to spread his jism over my stomach and breasts. It was warm reminding me of hot oil during a massage so I asked Sidney to rub it into me. He readily obliged while simultaneously rubbing my clit again to bring me to another climax.

This sensual massage lead to more kissing and I didn't even notice that Ben and Jack had left us alone. I heard what I believed was the breaking of pool balls and male laughter from another room. More kissing and my hands roamed so that I was now cupping his face in my hands and looking into those eyes. He broke our kiss and gazed at me and then he took a deep breath, releasing a sensual sigh. I sensed how nervous he was so I deeply kissed him again. I brought my hands to his chest, pressing hard while he wrapped his arms around me. It was like a magnetic pull of two magnets of polar opposites. He forcefully pushed me away and looked at me again. I once again shivered with it's intensity and he responded by laying me back on the couch and resting on top of me. I could feel his hardness, his erection through his clothes as he started to sensually move his new manhood into my groin in slow circles.