The Hook-Up

She was kneeling face down on the hotel bed, her light cocoa skin reflecting the soft lighting from the lamps and the light from the slightly parted curtains. Her ass cheeks spread open by her two hands one on each cheek, the white gusset of her silky lace panties pulled to one side revealing the darker wrinkled skin of her exposed and distended anus which glistened, slightly moist, her balls and cock hanging down, one testicle still caught up in the flimsy fabric. I knelt on the floor taking all of this in for a moment, the blood rushing to my head, feeling like I had stumbled onto the set of a porn shoot. I could smell the warm muskiness of her emanating towards me, enticing, forbidden, erotic.

This was my first time - my first time in a casual no strings attached hook up with a cross dresser I'd met on-line - and my first time I had ever stepped out on my wife of 25 years, Vicky. I was conflicted with guilt and lust, and Coco's ass was looking very inviting, and she was moaning in a soft husky voice. My lust won out, and I moved my nose to her ass pussy, breathing her into me.

As part of Coco's on-line profile, she has specifically invited men who are great ass eaters. I was certainly into eating ass, and the sight of Coco's inviting anus was nigh on irresistible. As my face got closer to her, I could feel the heat coming up from her and I knew that once my nose, my tongue, made contact with her softness, there'd be no turning back. Hesitantly at first, I extended my tongue towards that sexy and intimate place.

### 01: Prelude ###

Let me back up for a moment. Context helps.

I've been with Vicky for about 25 years. I've been an ardent admirer of trans women for about as long, having first encountered the early scanned photos by "Red Toe" and "Captain Jack" of Color Climax, etc. which were on the BBS boards and Usenet. I remember becoming entranced with the sensuality and taboo of Dana Douglas, Gia Darling, Olivia Hart, Foxy Angel, Vaniity, and all the rest. This pre-dated the Grooby franchise, but the Usenet groups were active. Then came Androgeny On-Line and a slew of other sites. Just pics because video was too resource heavy.

Now, the Net is awash with transwomen, and images and videos are so easily accessed, and overwhelming. I never really felt attracted to the silicone look, preferring TS women with hormone breasts. Now, there is a fresh wave of gender-bending eroticism with the so-called 'traps' and 'femboys', many of whom I also find very exciting to watch and look at. I don't know their names, aside from rare occasions because the files one can download for free do not keep good records. But I remain mesmerised by the incongruity and the taboo of wanting a feminine person who comes sporting the same equipment as I do, and how this subverts all of the old and oppressive discourses homo-eroticism entails.

These images are a staple of my masturbatory fantasies, and I cannot even begin to count the number of times I fantasised about hooking up with one of these models and enjoying every taboo inch of their sexuality. I am trans amorous, and yet, for all that, have never knowingly met anyone in the flesh, far less openly expressed my desires. Yet, as I get older, I recognise that there is a part of myself that is being left to wither. Considering the amount of time and energy I've invested in this guilty secret over the years, it is evidently a very significant part of me too.

So, I pushed the boat of risk out a little further and signed up to an on-line TS/TV chat and dating site, and then searched for who else was in my area. Quite a few, but - and to be blunt - although I greatly admire the courage of many cross dressers and the strength of their convictions - if I was going to push the boat out even further, then I needed to feel attracted to the person. Moreover, many on the site seemed mostly preoccupied with hanging out with other cross dressers. Even in such a world, men seemingly have a crap reputation.

After some casual browsing, I began to relax and to tell myself that this part of me would remain a fantasy, and that I wouldn't realise it. That is until I came across Coco's profile. Coco advertised herself as a cross dresser, glamorous, young and, amongst other things, interested in hearing from men who were great ass eaters! Her pictures showed part of her face, and her (clothed) body, and she certainly seemed slim, attractive, and definitely had a very edible ass. I dropped her a private message telling her so.

By the next day, Coco had replied, thanking me for the 'sexy message' and asking 'when can I have you hun?' I replied, and we bantered for a bit via the messaging facility before taking the plunge and deciding to meet up. Neither of us could accommodate, and due to our personal circumstances, we could only meet during the day times, so we scheduled a meet at a local day use hotel in an accessible part of the city, and agreed to meet in the hotel restaurant and to have a coffee and chat first, to break the ice.

### 02: The meet ###

The appointed day arrived. I went to work as usual, although varied my morning ablutions slightly to ensure that my cock and balls were clean shaven and smooth, and that I wasn't wearing any beard stubble that would scratch Coco's sensitive areas. The morning passed slowly, and I distracted myself with busy work, not really able to concentrate on anything, and willing the clock to reach 12:30.

Eventually it did, so closing down my computer and getting up from my desk, I told my colleagues that I wouldn't be back until much later, if at all, as I had a couple of back-to-back meetings lined up with clients. Then I was off.

I walked the ten minute path across town to the hotel, entered the lobby and headed for the restaurant. I looked around for Coco. I already knew that she would not be dressed up - she was too shy and lacked the confidence to pull it off, she had told me. I had texted her on my way to work to tell her what I was wearing, and so I selected a table and sat down.

After about ten or so minutes, a willowy, tall dark skinned man walked up to me and asked "Are you Eric?" I looked him up and down, took in the full lips, and the slender build and nodded in the affirmative. Suddenly, he broke into a smile, exposing his white teeth and said, "I'm Coco," and sat down opposite me, resting a large bag on the floor next to him.

I smiled back warmly and asked if he fancied a coffee, and then ordered two from the hovering waiter. As we waited for the order to arrive, we were checking each other out. I smiled again, and said softly "I'm glad you could make it, Coco. This is a first for me, so I wasn't sure how long I should wait before my nerves got the better of me."

Coco smiled back and answered, "I know what you mean. I was watching you for a few minutes, just to see if you were ...," he paused, "uh - I dunno - okay?" The voice raised inflectively as a question, before he continued. "I am kinda nervous too. Not quite sure what to do. You look okay. You don't look mean or anything ..." His voiced trailed off.

I joked, "Well, that's good to know!" Then I continued, "Look Coco, I know we are both taking a risk, and I'm not into pressuring you. So how about this - I buy the coffee and pay for the room, and I want you to know that you are free to leave at any time. I want you to know that there are no strings attached. What I do want though is for you to stay only because you want to, not out of a sense of obligation. Okay?"

Coco looked at me steadily, his dark eyes framed by high cheek bones and soft hair. His face, as I looked at it longer was actually quite effeminate. It was soft, no hard angular lines, no stubble, and he seemed to have naturally quite long eye lashes and thin eye brows which arched above his eyes. As a man, I registered, he was already attractive, even though that is not something that I ordinarily would clock.

Coco opened his mouth to speak and said, "That's nice of you. Thank you. I think that I am already beginning to feel safer here with you, more relaxed." He was about to continue when the waiter interrupted him by placing coffee and the fixings in front of us. I thanked her and waited until she was out of ear shot, and then leant forwards.

"I think you were going to say something?" I encouraged.

Coco nodded, and continued, "I was going to say that I tend to only dress up privately, but I've been with guys a couple of times now. But it always feels new. Scary."

I nodded and said, "Well, let's relax and take our time. We're both taking a risk being here, we both seem to accept and respect that, so that's a good place to start, right?"

Coco nodded, and smiled, and added some milk and sugar to his coffee, stirring it in.

I leant back in my chair, and said, "Why don't you tell me a little about yourself? Maybe, what do you do when you are not hooking up in a hotel," I smiled.

I think Coco blushed, and then said, "I'm a university student. I am doing my final year in pre-med, so have very little time, and the pressure is crazy."

"Wow," I replied, "that does sound tough. So there's a sharp brain behind those lovely eyes," I added, realising that I was beginning to flirt with him.

Coco chuckled and said "I wish - it is all such hard work!"

Our conversation ranged across the usual topics, and as we relaxed I felt more comfortable exploring aspects of what had drawn us to meet like this. I asked Coco about when he had first discovered his feminine side, and his journey of giving it a voice, and he told me of he had grown up always feeling strange, different from the other boys his age. He spoke of how he liked soft feminine things, how he enjoyed the company of women, and how he felt attracted to men. He began to open up to me and to let me into his secret side, revealing that he had discovered how pleasurable it was to stimulate his anus, how he fantasised about being submissive to an older man who appreciated his femininity, and how he found a guilty, even shameful, pleasure in dressing up. He had stolen underwear from female friends, and then summoned up the courage to buy his own lingerie on-line.

As I listened, Coco began to take shape as a whole person, escaping the easy and lazy binary classification, and becoming multi-textured, rich in their own unique being in the world. I found myself coming to respect him/ her/ them as multi-faceted, trying to work it out along the course of their experiencing the world and trying to make sense of a world which tends to be cruel to those who do not fit neatly into the prescribed boxes.

We chatted for a while, finished our coffees, and then it seemed like the moment of truth was upon us.

"How would you like to do this then, Coco?" I asked. "Would you like me to get the room, and if so, did you want to go upstairs ahead of me and get yourself fixed up?"

Coco nodded, and said, "Yeah, I'd like that. Maybe half an hour?"

I agreed, and told them to wait at the table, went over to the reception desk and booked us a room until 17h00, prepaid and accepted the pass key. I returned to the table, gave Coco the card and said, "I'll come up in half and hour and knock three times, pause and then twice. Then you know it's me. Put the 'Do Not Disturb' sign on the door. The room is 722." I kissed the tips of my index and middle fingers and placed them against Coco's cheek. They smiled, touched at the gesture, collected their bag and got up.

"See you soon, hun," Coco said blowing me a kiss, and turned and left my field of vision. I checked my watch, ordered a second coffee, picked up a sheath of papers from my bag, and distracted myself for the 30 minutes before I could follow them upstairs.

I knew that I wasn't really reading the printed text on the papers. My eyes were staring at the paper, but my mind was elsewhere. I was already upstairs, and wondering what would be waiting for me when I got there. In person, I reflected, Coco was charming, articulate, honest. They were also attractive, physically. I realised that I had dropped the use of a male or a female pronoun when I thought about them. This was because I recognised that they didn't really fit either category. Biologically male, yes. And yet, many of their mannerisms were strongly female, and their body and face were feminine too. Coco had told me that they liked being thought of as a woman when dressed, but that didn't help me out when they were here with me in public, dressed in casual street wear as if they were strictly a male.

Not for the first time I recognised just how screwed up our society is, with all of its labels and biases and judgements. How quick to condemn and how slow to accept difference the social system seemed to be. I wondered whether it would be easier for future generations to find acceptance for simply being whoever they were, however they might identify. It was human sexuality, and let's face it, there is nothing more fluid, more resistant to labels than authentic sexuality. The body wants what the body wants. Our minds struggle to keep up after the fact.

Eventually, the last minute of the agreed half hour waiting period grudgingly ticked by, and without further delay, I paid the cheque, collected my belongings, and headed to the elevator to go to the seventh floor, and whatever destiny might have in store for me.

### 03: The encounter ###

I knocked on the door of room 722 thrice, pause, and then twice. I leant towards the door, noticing the sign on the handle dissuading disturbance, and hissed "It's Eric."

I heard the latch click metallically, and the door opened inwards. The room was dim and Coco was backlit, her features hidden in the shadows. However, I quickly noticed that Coco was now dressed in a long red satin dress, with heels, and wearing a long straight wig, which framed their face. Dressed, they were now a she. She stepped to one side, giving me access, and I stepped into the room.

Coco shut the door behind me and as I stepped into the vestibule, I turned to take her in. Her tall, willowy frame was perfect for the dress she had selected, and it hugged her like a sensuous glove, refracting light in small sparkles and shimmers as she moved. Coco in motion, dressed like this, was like a cat - smooth, each deliberate step unhurried and without waste. She was wearing matching heels which accentuated the length of her legs and the contours of her calf muscles, the hem of her dress a few inches below the curve of her generous buttocks. She had applied make up, her full lips enhanced with a rich red gloss, and her eyes sparkled in the dim light. She looked lovely.

I asked her, aware that my breath was unexpectedly catching in my throat, "Do you mind if I open the curtains a crack - I'd love to see you properly?"

Coco replied softly, although I could hear the soft tremor in her voice, "OK, but not too much. I don't want to ruin the fantasy".

I nodded, adding as I reached for the draw chord, "I don't think there's much risk of that babe - you look great!" A statement that was actually confirmed as the afternoon sunlight crept back into the room, illuminating Coco in her snug dress, her wig, her make up and her heels. She looked really good, really passable and, I realised, really desirable.

"Oh yes," I hissed as I took her in, now illuminated slightly. "You look too good to hide in the dark, babe," I reassured her.

I saw Coco visibly relax, the tension easing out of her, and she smiled at me, her white teeth shining between her full red lips. I looked at those lips and recognised just how kissable they appeared. "So now what?" I asked a little breathlessly.

Coco stepped up to me and said, "Well, why don't you take me in your arms and kiss me?", and before I could even agree Coco was up against my body, her body pressing against mine and I could feel her warmth through the layers of our clothing. My hands ran down the length of her spine, tracing the vertebrae through the satiny feel of her dress, and without waiting for permission, my right hand cupped her left cheek and squeezed it, pulling her more tightly against me. Our lips met in a sudden passion, her full lips mashing up against mine, her mouth opening to take my cautiously probing tongue.

Then, our tongues were together and we were sighing into each other's mouths, our bodies beginning to heat up as we pressed against each other. She was so warm and curvaceous in my arms. I enjoyed the feel of her hips against me, the firm rise of her ass under my stroking hands, the tightness of her body, and I began to feel her getting stiff against my groin.

We embraced, her running her hands all over my body and me running my hands all over hers. I snaked a hand under the hem of her dress, touching warm, smooth skin and moved upwards under the material. She sighed softly against me, our mouths still locked together, our tongues still engaged in deeply exploring each other, and my hand traversed the rise of her ass cheek, ruffling the material of dress in a bunch as I did so. Coco's ass felt so warm, so firm, and I thought back to her profile statement inviting 'great ass eaters', and found myself increasingly excited at the prospect of exploring her ass, of smelling her, tasting her.

My left hand found the zipper at the side of her dress, and gently pulled it downwards. Coco murmured her consent and as the fabric fell away she wriggled until the dress began to loosen its tight embrace of her body. With my right hand now (reluctantly) releasing her buttocks, I pulled on the material on the opposing side and pulled downwards, and Coco stepped out of the dress as it fell into a puddle on the floor at her feet. She was now naked, aside from her red heels and, I realised with a quick thrill, a thong, permitting me to stroke the globes of her ass in long gentle movements with little interruption, before I began the return journey across her delightful curves.

Coco felt so good under my touch. Her ass cheeks were smooth. I could feel the taut muscle under my fingertips, the epidermis yielding slightly to the pressure of my fingers. I stretched a cheek up and outwards and felt her gasp slightly in my mouth at the audaciousness of this sudden exposure. She seemed to like it when I took charge, and given how sensuous she felt, I was only too happy to take the lead. I wanted Coco naked. I wanted to see that ass, I wanted to smell it, I wanted to taste it, and then I wanted to fuck her.

### 04: Engagement ###

My own arousal drove me onwards. I broke our embrace and spun her around so that she was facing the bed and then pushed her forwards so that she landed onto it. She gathered herself to her knees, her full buttocks pointing upwards, the tiny thong barely concealing the cleavage of her cheeks and the spicy anus that lay between.

I removed her heels, and pulled her thong to one side, and there she was - exposed for me to feast my eyes upon her. Her anus, dark and wrinkled lay before me, and I could already smell her musk. I pulled her cheeks apart and her anus opened slightly, parting as if to invite me to come closer. How could I possibly resist? I realised that I was already powerless, overcome with a deep longing, a primal lust.

She was on her knees, her thong off to one side, her genitals having escaped the tight enclosure of the gusset and hung down in anticipation of being touched, her penis already engorged.

On my knees at the edge of the bed, I feasted my eyes on Coco's offering and drew closer, smelling her, already beginning to salivate. I reached my hand between her legs to cup her generous balls and the warm hardness of her cock. Aside from my own, I have only touched another's cock once before, and feeling the weight and warmth of Coco's cock in my hand pushed me into another level of sudden arousal. I wanted her - all of her - in that moment.