The Trade Show Pt. 08: Boobs First

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*****

As I rode Cindy's shaft, enjoying varying my position to both enhance her and my own feelings, my mind drifted, dreaming of what lay ahead for Georgia, and how I would handle transitioning at work.

Immediately, of course, doubts crept in and I was jolted back to reality as Cindy played hard ball with my nipples causing me to orgasm unexpectedly quickly, and noisily too. She had quickly learned how to reach my g spot. The result was a stream of cum launching across her animated tits onto her face. She laughed and just kept pumping me whilst I continued to orgasm noisily. By the time I was done, Cindy had cum too and we were both covered in the moist sweat of sex, locked in each other's arms, me still impaled on her strap on.

By clenching my tgirl pussy, I had discovered the other end of the strap on would rub her g spot causing her to cum again in small and successive waves of delight. As she squealed and wriggled, I felt the feedback directly through the flexible shaft, causing rather pleasant feelings inside.

"Life is good," I thought.

After a shower and breakfast, both still only dressed in gowns, we had a long conversation going over what we had discussed the previous night. Moving ahead. Becoming Georgia. That magical, but always out of reach and scary word, Transitioning.

Cindy held my hand tight and comforted me all of the time. At times, we both cried together. Cindy understood how important this was to me, but also how difficult it was likely to be. We were both scared in case, for any reason at all, it may lead to us becoming more distant.

We agreed to make a list of what was most important, to each of us, and what was least important. That way, we thought, we would focus on the key things first.

I found a pad of paper and a pen and we started a list with two columns. One for me, and one for her. We agreed to score each item from 1 to 5. 1 being not important at all, and 5 being very important.

We knew that each of us would probably end up with completely different priorities but also agreed that compromise would be reached if we really loved each other.

The list turned out to be very comprehensive and far longer than we first thought it might be and included things that were, frankly, of very minor importance and superficial, to those of huge importance, and we wondered if the whole exercise was going to become too calculated. Too much from the head rather from the heart, but we agreed to do it and see what resulted.

Some of the items were: hair length and colour, body hair removal, boob size, bum size, removal of Adam's apple, facial re-shaping, voice training, hormones (what, how, if), ability to have an erection, swapping penis for vagina, etc. etc.

We agreed to take the lists away and each score it separately, but brutally honestly.

Cindy dressed and after an emotional goodbye left me alone at home. It is fair to say that my mood swung between emotional highs to lows. On one hand, a new future as Georgia with Cindy was there for me to grasp, if I decided to choose it. On the other hand, there was the fear associated with the unknown and possible very difficult life as a trans woman.

In my spare bedroom, I dressed for work, although I had already tucked and put on some gorgeous black lace knickers that Cindy had bought me. "That will be enough for me today," I thought to myself as I dragged on my normal work attire. Chino's and blue Oxford shirt.

The following few days dragged and I could not wait for the weekend when I would again be with Cindy. She had become my life, almost since our first contact at the trade show in Wadebridge. As if to remind me how much I missed her, she regularly sent me short messages. Some checking to see that I was OK, and some designed to arouse and distract me. One was simply an upskirt selfie, with her fingers inside her. Just the distraction I needed!

After a full week at work, I knew I had to make changes, but this simply added to my stress levels.

Each evening, Cindy and I would talk on the telephone for hours, and we eventually resorted to Skype.

Cindy had started to complete the table but was finding it hard t decide how to score some items. In adding her scores, she was taking too much time trying to take my views into account. I explained to her that she must only consider her own views. What was important to her. What she would like if, say, she was able to design a Georgia for herself.

During our conversation on the Thursday night, I asked Cindy to add some extra items to the list, and she went to get a pen. I read them out to her, knowing that they would prompt some comment from her.

"Real boobs v falsies. House move. Job change."

There were a few moments silence whilst she added the items and then thought them through.

"OK," I said, "Do you understand what each of those mean?"

Again, there was a pause.

"Yes, I think so," she replied. "But maybe we should talk them through first."

"Good idea, no problem. OK. Boobs first then," I said.

"Always," she said. "Definitely boobs are always first." We laughed, and I was pleased that Cindy was not becoming overwhelmed about the whole list idea.

"Hormones will slowly give me some boobs, but at my age, I am unlikely to ever get much more than a B, at a stretch. I am an A at the moment. I was wondering if I should get breast augmentation. I think this is possible provided one already has some breast growth, and so it would be something we would need to take some advice on. I wouldn't want to look like I had two grapefruit halves glued to my chest!"

Cindy laughed. "Neither would I," she said. "I'd give that a 5. I'd love you to have real boobs and as we said, a C would be great. I could really have fun with them!"

"I think consultants, good ones anyhow, advise what is best, and what suits one's frame," I said. "In fact, some have ways of letting you see what you would look like with different size implants, meaning one is less likely to be disappointed afterwards."

After a short discussion, we moved on.

"On the house move," I started, "I thought" and before I had time to finish, Cindy interrupted.

"Why don't you move in with me?" she said, or rather stumbled it out, at twice normal speed.

As she looked at me, trying to determine my response, which on Skype is not as easy as when face to face, she blushed. This was a rare thing, I thought.

As I started to answer, again she interrupted me. "Look. I have given this some thought. It must be hard for you, staying in your old house, and this would provide a solution, even if it were whilst you looked for something else. Being a cash buyer is always better. And anyway, we could see each other every night!" She grinned a nervous grin, worried in case I turned her down, I guessed.

"Darling Cindy," I started, "That is a wonderful invitation and one which I am inclined to rush at accepting, but you have to look at your own needs too. You have other friends, and sometimes sexual partners who come to your house, and it would no longer be your exclusive private place. We have never talked about exclusivity before, and I am not sure it is something you may want. I don't want to be in your way."

Cindy held a straight, thoughtful face for a moment, as she took in what I had just said. I too wondered if I had just given her the impression that I was also seeing someone else, or at least wanted the option to be open to me. I started to dread her response.

"You can be a proper ass sometimes, you know," she said, with a wide grin on her face, "If I were there, I would give you a smack on that cute ass of yours! I know that I have a healthy sexual appetite, and I can be bi, sometimes, but actually," she paused, clearly thinking carefully what she was going to say.

"But actually, I love you, and you know me pretty well by now and, well, I do love you like nobody I have ever known before. I mean I really love you, and you love me too and so this is something we can sort out between us. Anyway, since I have met you, I really don't feel like meeting anyone else. You give me everything I have ever needed, and more. I can be exclusive, and will be. I would not cheat on you. Please move in with me. Think of the fun. No more Skype for starters!"

I concluded that Cindy was genuine, even if she struggled to put it over that way, but I also considered if I could also be exclusive. After all. She was a woman, and by default, didn't have a real cock. What if I decided one day that I wanted one inside of me. Maybe in my new pussy. I wondered if the hormones would have that result, make me more attracted to men.

And as a woman too, she may decide she'd rather fancy a cock too, and by then, I probably wouldn't have one of my own.

As these thoughts ran around in my head, I wondered why life as a tgirl had to be so f**king complicated.

"OK," I said, "Let's add that to the list too and get all our scores done by the time we meet tomorrow evening." Cindy agreed.

"One last thing then, Job Change," I said, and as I waited for an answer, Cindy lifted off her tee shirt above her head and removed her bra, leaving her gorgeous boobs to move around like two puppies just let off their lead.

With a glint in her eye, Cindy asked "Wouldn't it be really nice if you were here to play with my friends?" simultaneously cupping her breasts, pinching her nipples and closing her eyes, as if in ecstasy.

"That's not fair!" I exclaimed, as feelings of arousal spread through me. "We need to focus, on the list, not on your lovely teats."

As I blushed without any real reason, Cindy simply continued with her nipple play, suggesting that I join her and play with mine too. This was not phone sex, but Skype sex, and I concluded that it had possibilities.

"OK," I said, struggling to concentrate, "I have decided to leave my present job, take a few weeks off, and then decide how best to get a job as Georgia. This will not be easy, and it will most certainly mean a much lower salary. I may have to become self-employed and, basically, work from home."

Cindy stopped her cam show and folded her arms, giving me a stern look. Meanwhile, I was fascinated how she managed to fold her arms around her fabulous boobs which were spilling out in all directions. I concluded it would be easier when wearing a bra, and looked forward to finding out myself one day, when I had my own boobs. This led me to consider having D size breasts rather than just C. Decisions, decisions.

I was interrupted by Cindy. "You may recall I suggested you could come and work for me, or rather, my company," she said. "I can understand why you may have thought it not a good a idea, at the time, but there are lots of really good reasons it would be a great idea. You would be really good at the job. I have seen you socialise, and flirt, and you would be a real asset, for the firm, if not a rather gorgeous ass too." She said, grinning cheekily.

"We would certainly pay a lot more than you earn in your present position."

"If you lived with me, you could share transport. That would be really good, as I could fondle you in the traffic jams."

"We also have a fantastic benefits package, which in your case would include me, of course."

We both laughed, but Cindy was serious with her offer, and it was something I had thought about over the recent weeks. My main concern was the same as every trans person in the world had, I guessed. How would I be accepted by colleagues and clients?

"I will admit," I answered, "to having thought about your suggestion more than once since you first mentioned it, but there are so many things to consider, I think we need to talk about it at the weekend, but thanks for the offer, it is really special but it scares me more than just a little."

"Sounds like a plan," said Cindy, "I'll give that one a 5 too! You could always spend a couple of weeks in the office, as a consultant if you like, to see how it pans out."

With that, Cindy continued to seduce me on Skype, and I travelled to her place on Friday evening ready for some serious discussions, and a weekend of wild sex!

I arrived later than planned and Cindy was already in weekend mode. On the sofa in a silk gown with a bottle of red on the side table. Her hair was clipped up in a "couldn't care less" fashion and I marvelled at this new image she presented. Despite being right at the extreme end of casual, to me, she seemed hotter than ever, in a kind of Marilyn Monroe sort of way. Oozing sex appeal without even trying.

I imagined her wearing some secretary type glasses, peering over the top of them at me, and instantly became aroused at the thought.

(Mental note to oneself: Get counselling!)

Greeting me with a long tongue induced kiss she sat down on the sofa again, looking weary.

"I've put some dinner in the oven," she said. "Nothing very special, but I've had a bit of a week and I thought we would just chill out this weekend."

"Sounds rather wonderful," I said, as I joined her on the sofa arranging her head in my lap and staring into her eyes.

I was tired too, although more from stress than from anything else, and so we chatted, ate dinner on the sofa and watched a film on Netflix before turning in early.

No sooner had we got into bed than Cindy was fast asleep. As I drifted off too, I wondered if she was well, or really just very tired.

I woke up to the smell of frying bacon and an empty bed.

After a quick wash and brush up I slipped on my gown and followed the smell to the kitchen.

"Hello Gorgeous," said a very buoyant, smiling Cindy, "Sorry about last night, I was completely exhausted."

"That's OK, I was beginning to wonder if you were coming down with something," I answered.

"I'm fine, really. And definitely not cumming, or going down right at this moment, thanks."

Yep. Cindy was back on form, and I was very relieved.

I hugged her from behind, fondling her boobs through the silk robe whilst she continued to prepare breakfast.

Trying everything to distract her from her focus on food, only when I knelt down and slipped my hand between her legs and engaging with her labia and clitoris did she finally turn around to face me.

"Now behave yourself," she said, with a wide grin, "How am I supposed to finish breakfast if you have your fingers in my fanny?"

She had such a way with words, I recall thinking.

As I stood up, she reached inside my gown, grabbed my erect cock, and kissed me with such force I almost fell over backwards.

"Now go wash your hands, set the table and I'll be there in a moment," she said, tugging lightly on my shaft, and so I did.

As we ate breakfast, Cindy explained that she had been wooing two possible new clients and that it had been a tough task. Much harder than usual, and she hoped this was not a sign of a future trend. She also said that she found allocating scores to our list quite stressful too because she found it impossible not to consider my wishes alongside hers.

I was touched by her kindness and consideration and assured her that we could ignore the list and agree things between us, taking it as it comes, if she preferred that. I also reassured her that the two awkward customers were just bad luck, and not a trend for the future.

As I washed my hands, I rebuked myself for making the list. That was such a guy thing, I thought. Not good.

She seemed much happier with my response and after breakfast she simply let her gown fall to the floor, bent over the table and asked me to bring her off in any way I found suited me best. Yes, Cindy was definitely back to her usual self.

And so, given that I already had an erection, I slipped my cock into her anus whilst simultaneously fingering her now engorged clit. She came very quickly, and well before I was ready.

She turned around before I had finished, took my hand and led me at some speed to the bedroom where she pounded me with her strap-on until I was exhausted, having cum three times in quick succession. I had become to love anal sex and the climaxes that came with it.

We showered and both dressed casually in skinny jeans and strappy tops. Cindy worked on my hair and makeup, which she really enjoyed, and we decided to head to the coast path for a walk and maybe café hunting. This was quite a change for Cindy who, more often than not, would have a far more detailed plan for us.

We walked toward Newquay and stopped at the hotel on the cliff for lunch. The view inspired us both as we watched the waves crashing onto the rugged cliffs.

After lunch we went down on to Fistral and walked on the beach, hand in hand, carrying our sandals as we paddled at the water's edge. We were two people in love, not needing to do anything other than be in each other's company It was an idyllic day.

On and off during the day, we returned to working out how best to smooth my transition, but it nearly always came back to the same question. Would I work for Cindy's company? This decision clearly needed to be made very soon, and it weighed on my mind.

We concluded that we should prioritise changes which would make it easier for me to pass in a working environment. Key things to do first were hormones, boobs, voice training and sorting out my hair length, once and for all. Previously, when on hormones, I found that my hair grew very well and I was able to manage without a wig. I have always found them unbearably hot in some circumstances and so we decided that whilst they would provide a short-term solution, the longer-term aim would be to grow my own and add extensions.

That evening, dressing down more than usual, we went into Truro for dinner and cocktails afterwards. In all, Saturday had turned into a day to chill and re-charge our batteries. Cindy and I had become inseparable and completely absorbed in our own company, although we were regularly approached by guys wanting to buy drinks. Every time this happened it boosted my inner confidence, knowing that I could pass, even in poor light.

On return to Cindy's we simply put on our nightwear and drank hot chocolate on the sofa, comfortable in each other's arms. When we retired to bed, we explored each other's bodies bringing each other to a climax before drifting off to sleep.

Sunday morning was another thing altogether and I awoke to find Cindy dressed in red lingerie, red stockings and her strap-on harness, sucking on one of my nipples and squeezing the other through the silk.

She was purring, smelling like a bed of roses and oozing sex like a brothel.

She said that she had a surprise for me and leaned toward the drawer, pulling out a purple package. On opening it, she revealed a new dildo for her harness.

"Shit!" I exclaimed, "That is one fucking big cock!" I think I even blushed, as I realised her intentions.

Cindy grinned, a wicked smile. Her bright red lips shone with lip gloss. "I thought, as you seemed to take my normal cock with such ease, and as you said how great it feels when I put it in all of the way...well, I thought you may enjoy a bigger one. What do you think? Are you in the mood to try it?" She handed to new purchase to me to examine.

Still blushing like a beetroot, and studying the new weapon, for that is what it looked like, I wondered how something that big might fit, and more importantly, how much it may hurt. It looked to be at least 10" long, and about twice the girth of my own cock, maybe more.

Whilst I contemplated, Cindy had slid down me and having raised my legs was rimming me and slipped a finger inside me.

I moaned slightly as she peered up at me and continued to ream me with her finger. Still only partially awake, I closed my eyes and focussed on her actions. She was very good and had learned exactly how to quickly excite me.