Chis(topher) & Chris(tina)

Me: I’m from upstate New York, a small redneck, dying, sleepy, town stuck in the 1960’s. I came out to my parents in my senior year, with some resistance, they gradually accepted it, otherwise I was closeted, you see it was not accepted there. I Graduated high school, left for college in New York City, majored in advertising. I got a great internship, with a major advertising firm in the city, I stayed on part time until I graduated, where I went full time. I got a flop house studio apartment, which at the going price, I could barely afford, but my potential rapid advancement should make it easier sooner.

Chris: Chris grew up in the suburbs of the New York City, he got a great job paying low 6 figures, for a very conservative law firm, as he moved up the ladder quickly. Chris was out, except at work, yes he lived a double life, while he preferred Christina, he always played Christopher at work. Very few select trusted coworkers knew of his double life, otherwise it was don’t ask don’t tell. However he was content with his situation, didn’t mind it, and lived with it. Chris is a very handsome but slightly feminine in stature, he’s all man while in his 3 piece expensive conservative suits, which helps hide his feminine side and slim unmuscular build, but all girl when he changes into his so called “play clothes”. He has somewhat longer sandy blonde hair, but he combs it more masculine as Chris, but his look is completely all girl when he combs it as Christina, I envy the way he can change his hair style and it changes his/her whole look.

* * *

I met Chris at my advertising firm about a year ago, his firm represents ours and he came in to go over several things with my bosses and me. Ultimately we went to lunch, and I sat with him and we hit it off quite well. Later that night, he texted me, as we all exchanged business cards and mine happens to have my cell number on it as well. He identified himself and suggested we get drinks after work some day. Flattered by what seemed to be a non business, more personal, “I’m interested” worded text, or was I wishfully reading into it? Anyway I willingly replied, “sure, you name the day, and I’ll be there”, I hit Send….. was that too bold? Hum, maybe, oh well let’s see where it goes, or if it goes, maybe I was too eager.

About a week went by, I figured I might have scared him off, when my office phone rang and it was him on the other line, figuring it was work related, I was polite and said “oh hello Chris, how can I help you?” He replied “go out with me tonight”, as I was taken back, never expecting him to be that forward. I thought what the heck, and I said “sure, I thought you might not be interested and I may have read you wrong”, he replied, “oh boy I am interested, but I have a situation”. “Oh what’s that” I said, he said “we’ll discuss it tonight, meet me at 7 at Clancy's on Fulton, do you know where it is”? I said “sure do, been there before”. Clancy’s is what I’ll call a “gay friendly bar”, where the clientele is a least a 50/50 mix.

I arrived early and took a seat at the bar, ordered a drink, and scanned the crowd for Chris. He wasn’t there yet, but I was early. A cute young girl sat next to me, but I wasn’t paying much attention, as I wasn’t interested, other than she had a smoking hot slightly overdressed red dress on. I began to worry by 7:25, and thought maybe he chickened out. The girl next to me began to make friendly small talk, she made me feel comfortable, and we engaged in light conversation. Suddenly she seemed quite familiar, wait… what…. Is it?…. “Hey…uhh.. Chris”? She replied “yeeessss”? And waited for my reaction, she said “it’s me in all my glory”,…. “well”?…..“What do you think”?…… Still taken back a bit, I said “well, it wasn’t what I expected, but you are pretty hot”. He said “thanks”, as I ogled at the transformation, with that he,…. uh…. she…. stood up and did a brief runway type walk out and back. I was oddly attracted to her or is it him? Oh boy am I confused.

Anyway the night went on, we had several drinks and some bar food appetizers, we seemed to hit it off, but we called it a night and we parted ways. The next day, I was so infatuated thinking about the previous night, I texted him and offered another “date”, he agreed. We went to dinner that night and I discovered he…. she…. still lived in the suburbs with his… her…. parents, so when the time came we walked back to my little studio apartment, where I invited him up for a drink, and he agreed saying he couldn’t stay long as he had a big day tomorrow, he was not surprised by my meager furnishings or my twin bed, as it was just one room and not very big. We joked about the midtown prices and that he’s been looking to find a place of his own, as the daily commute really sucks, I said yeah I can imagine, I told him I was making a good very high 5 figure wage now and I’ve been checking out better places. I changed the subject and I finally got the nerve up to explain I was confused, and asked “what do I call you? He, she, them”? He laughed and explained, “it’s simple when I’m Christopher, I’m a he, when I’m Christina, I’m a she, just assume I am who I am at the time and as I’m dressed.” I laughed back and said “ I guess that is pretty simple. We continued to hit it off, and enjoyed each other’s company. We had a few drinks some light conversation and we parted ways again, after a quick kiss, I was fully aware nothing happened again, and wondered if it would, or if I read him more as a partner or a friend.

We occasionally crossed paths when he was at our office, but we always kept it professional, and used our cells for personal contact and our work numbers for work.

Our relationship did grow and we took it very slow, a few more dates and we decided to take it to the next level. Back to my place, as it was more private, I was nervous, and knew she was a he, but it was a situation I’d never imagined I’d be in ever. She sat on my bed, as I pulled a few beers from the fridge, instead of me returning to the only chair I had, I proceeded to sit next to her on the bed, she put her hand on my thigh, stared into my eyes, closed them as she leaned in for a kiss as I reciprocated, our lips locked in a long overdue roaming kiss repeatedly over and over. Before I realized it one of her hands was gripped tightly on my shoulder, and the other slowly inched up my thigh toward my crotch. I cautiously moved my hand to her knee and also slowly moved up her thigh under her dress. As I approached her crotch, I felt slippery, silky, lacy ladies underwear. Her legs felt soft and smooth, I reached a finger under the lacy leg hole sliding it in till I reached her smooth velvety scrotum, all the while kissing our way around our faces, neck and ears.

She undid my jeans and we worked them down to my thighs, she gently massaged my privates through my Andrew Christian underwear, my dick protruding the front out so far the leg holes were stretched away from my legs and she slowly was able to slide her fingers up under them into my own scrotum, which she slowly rubbed back and forth.

Before long, but very slowly we took turns undressing each other, she said, “I know I’m a girl on the outside, but your getting close to the boy I can tell you’re longing for on the inside, just keep in mind, I feel very feminine, and please treat me like the girl I am, when we get to the gift I’m willing to share with you. Now gently massaging our naked bodies, I touched her semi hard dick, and it responded with a spring to attention, I concentrated On making her feel absolutely wonderful by teasingly massaging her thighs, scrotum, dick and abdomen while suckling those little nipples. Her dick and balls were hairless, and so velvety smooth, I just wanted and couldn’t wait to taste it in my mouth, but I restrained myself until I was invited, again it seemed we were moving much slower than I was used to.

She took my dick into her mouth, leading me to assume that was my invitation, but I held off to be sure, she managed to get my dick and balls into that small mouth, a first time for me, she slid it out and concentrated on my shaft and head. I moved down to her crotch and spent my time roaming around with my tongue, never touching her dick with my mouth, she moaned please, don’t wait, take me in your mouth now. Well there it was my invitation, and I pounced, she came shortly after filling my mouth with her slimy cum, feeling it’s texture as I rolled it over her dick and my tongue, swallowing every drop she could spew into me. Chris was overwhelmed with her orgasm, as she tried to bring me to ecstasy in a similar manor, we were laying in a 69 as I could see some remaining cum leaking from her now flaccid dick, I reached out with my tongue to lick it off, her dick sprang back to attention. This got me so freaking hot that I blew my load with the thought, probably with or without her mouth. She lapped it up swallowing most, but saving enough to coat her finger by sucking it, as she reached around to play with my ass crack and she gradually after some time, slowly penetrated my hole. My subsiding dick now sprang back up again. She said she’d like to try the masculine role eventually and try fucking me but asked if I could fuck her first. I immediately flipped her over, grabbed some lube from my nightstand, and lubricated both her ass and my dick, I slowly arched downward sliding my dick up and down her crack, as she knowingly arched her back up, that was my signal to find and stop at the hole to begin to apply pressure, which I did, remembering she wanted to be treated like a girl. I worked my dick in ever so slowly until it was finally in, I heard her faint moans of pain as I did so, muffled by her face into the bed sheets. Once I was in and she began to relax as I laid still on top of her back, she began to arch under me again, we began rocking in unison, she then raised to her knees and we doggie styled for a while while I reached under her arch and began jerking her off, and it didn’t take long for me to reach my climax again, she insisted I cum inside her, which she didn’t have to ask twice. I then asked if she still wished to reverse roles and she said she never has but felt Moore comfortable with me than anyone else she ever has been with and thought it may fulfill my wants more which she said was her desire. So we reversed only I was on my back this time and she tried to enter me lubed up missionary position, and she pushed in quick, so quick I lost my breath and yelled quite loud, “OH FUCK” and she began to pull out saying she’s sorry to which I grabbed her ass and held her in, I wasn’t going to take that pain again. After a few moments I looked at her and giggled, explaining it’s ok, let’s do this, and she began fucking me, up and down left and right and she when she came she pulled out and squirted from my belly button to my face getting some in my eyes, now blinded I tried to wipe my eye. We collapsed in each other’s arms and fell asleep.

Within a few weeks we began looking for midtown apartments to share, we found one, and shopped for furnishings and moved in together. We now have great paying jobs, great after work relationship, the best sex life ever, and I enjoy both Chris’s as Tina and as Topher.

Stay tuned for part 2 where Chris meets my grandparents