tagTransgender & CrossdressersThe Trade Show Pt. 03

The Trade Show Pt. 03


I held both her hands in mine and stared into her eyes. "Can I ask you something?" I said.

"Of course," Cindy replied, "anything."

"You don't have to answer, and I won't mind if you don't, but do you have a partner, or husband, or someone in your life?"

She grinned. A huge beaming grin. "I am divorced," she said. "I have been for a while. We started out happy but somehow it never quite felt right. I don't think we actually loved each other, but I'm happier these days, and so is he. We are still good friends, which I love."

Her honesty impressed me and before I had chance to tell her my own situation she let go of my hands, lifted her jumper over her head, tossing her hair as she did so, and lifted away her loose bra. As she moved to unfasten her skirt I shook my head and she stopped. I turned her around and unclipped and unzipped her skirt, letting it fall to the ground as she turned to face me again. As she stood in front of me I recall letting out a huge sigh to which she simply tilted her head sideways and smiled. Neither of us had to speak a word. Her breasts were actually perfect. Probably a 40C, large areolae, and holding their position very well indeed. I judged that they were very natural.

From this point onward it all gets a bit hazy, but I will do my best.

As I reached behind me to unfasten my skirt she shook her head and laughed. "No way," she said, "It's my turn now, so turn around please."

And so I turned around and let her unfasten my skirt. She looked for buttons on my top but seeing that there were none she lifted it over my head, folded it, picked up both our skirts and placed them together on a seat. She led me to the bed and I climbed on, it was quite high off the ground. As I went to remove my heels she stopped me, just waving her finger as if to say no.

"I'll be back in a moment," she said, and disappeared into the bathroom. She then reappeared, her head leaning around the door. "Sorry, did you want to use the bathroom? I forgot there are two women in the room now!" I paused for a moment and said "Actually I will, but I'll use the one on the landing if that's OK". So I picked up my bag and freshened myself up, adding a small squirt of Paris perfume before going back to the bedroom. Somehow I felt completely comfortable walking around her house in lingerie and heels!

I returned to the bedroom to find Cindy on the bed, leaning on one arm looking directly at me. She had put on a set of the most amazing black lingerie complete with suspender belt and fully fashioned seamed stockings that wrinkled slightly here and there. She wore very tall red heels.

"Shit," I said. Not entirely what I should have said, probably, I thought. "You look stunning. A million dollars. Sexy. Classy. Hot. Jesus!" I said, trying to regain some sort of composure and sanity.

"Well you set the bar high and so I thought that I should at least try to compete," she said, with a grin. "Come here!" So I did.

She smelled wonderful and was more feminine than anything or anybody I could possibly imagine. We lay on the bed, exploring each other's body and talked about our wishes and dreams. She was gentle and honest and we shared an openness unlike anything I had experienced before. I wasn't sure that this was normal when two women talk, or was I just lucky. I remember thinking that this is how a marriage should be. A sharing relationship between two people with nothing remaining untold. I felt tears welling up in my eyes and seeing this in an instant Cindy pushed me onto my back, leant over and kissed me deeply. As she did she continued to explore me, feeling every detail of my lingerie and always pausing to explore the stockings and suspenders. I returned the favour teasing her nipples and running my tongue lightly over her labia making her squeal. Her knickers had a very convenient slit to ease my passage! She was very wet and her juices were flowing profusely. The smell was engulfing me and leading me to heaven.

After a while Cindy removed both her bra and mine and kissed and squeezed and sucked my nipples just as I had said that I liked it, causing me to wriggle and yelp as she did so. It was wonderful. Cindy was attentive and determined to remain in control. No longer was it my duty to be in charge and it was refreshing.

I removed her knickers leaving only her stockings, garter belt and shoes.

As she removed my knickers she asked "Is this OK? Do you mind? Just tell me when you want me to stop something." She was gentle and caring and we were indeed making love. This wasn't having sex.

I had tucked everything away nicely and it popped out looking rather sad, I thought. But I didn't mind. I was dreaming of having an orgasm by different means, one day.

Reaching over me to a drawer in the side table Cindy took out a dildo. It was fairly large. Certainly a bit larger than me at my best. She offered it to me and said that I could use it if I preferred not to fuck her myself. This woman was very special and we both used the dildo on her bringing her to orgasm several times.

She asked what I wanted to do and how I wanted to cum. After a short discussion she slipped off the bed and went to a chest of drawers on the other side of the room, returning with a black leather harness. As I watched her slip the dildo into it and strap herself in I realised what she had in mind. She returned to the bed and told me to move closer to the edge. She placed a pillow under my ass and spread my stocking clad legs to move between them. As I looked at her, her breasts swinging free, my legs with stockings and heels, it was an image that I had seen in my dreams many times.

Without touching my cock, which was no longer very limp, she lubed up the dildo and with a grin on her face she said "Now let's see if we can make some of your dreams come true." She gently worked the dildo into my TGirl fanny as she called it, adding lube as she went and as it slipped into me I gasped. I had used a rigid vibrator on myself before, although not often, and had used a dildo or butt plug occasionally but nothing felt like this. Whilst it was soft and lifelike it was also very rigid. The initial shot of pain as the tip entered me was quickly gone and she very slowly and with gentle pressure and back and forth strokes worked to get it into me further and further.

As she fucked me the feeling was intense. Like nothing I have ever experienced before. She played with my nipples, squeezing them hard in time as she entered me deeper. I can't actually recall too much what I did other than enjoy the experience. She was patient and pumped me slowly at first and then faster in short strokes until eventually the whole length of the dildo was entering me. I was unsure what length I would be able to take as I had seen many shemales who could only take a few inches. Cindy remarked how deep she was able to go and suggested that she buy a longer one for the next time! She said it was a shame not to be able to get it so that it pressed the top of my fanny and remarked that her ex was only able to take about two thirds of it.

As she added more lube she increased the speed and length of the strokes and continued to squeeze and suck my nipples. And then it happened. I suddenly came with little warning in a way that was more intense than I had ever experienced before, and whilst I spurted all over my corset and onto my face the feeling wasn't really in my cock. It was all over me and I was hot and sweaty from head to foot as I gasped and groaned. This I assumed was what an anal orgasm was like, and maybe even how women came, and why they made so much noise when they do.

Cindy was laughing as she slowed down replicating the natural thrusting movements of a guy. "Such a shame I can't fill you with spunk and let you watch it running out of your fanny," she said, "then you really know that you have been fucked". As I recovered with that image in my head I found it very erotic and my first orgasm was followed almost immediately by further small waves.

As I lay almost motionless she removed the harness and lay back on the bed next to me. I wondered how she was feeling and felt slightly guilty myself for not having fucked her.

"How do you feel?" she asked, as if she knew my thoughts.

"Rather well fucked," I said, "I can't even begin to tell you what it was like. It was the best sexual moment of my life, how was it for you?" I asked, looking into her eyes with a slight frown.

"I fucking loved it," she said," I actually came whilst I was fucking you. The dildo is designed to do that I guess, and I really love pegging." We rested on the bed and continued to talk and play with each other. I managed to get her to orgasm a few more times that afternoon.

We showered and dressed and shared thoughts over coffee and cake.

"I think there is something we should do," she said.

"I haven't the energy," I joked.

"No, really, there is something we should do. Something that you should do."

"OK," I said, humouring her.

"I think we should get you properly fucked, by a guy, a real hunk." Cindy grinned a wicked grin.

I sat upright and I think must have looked shocked. "Now hear me out," she said. "Don't get me wrong, I am going to fuck you again, and again, and I'm not going to share you with anyone else, but a dildo isn't like a real live warm throbbing cock. But you know that, you've got one!" She laughed. "I know a guy who is bi. He is really good. Really good. You'd like him, and his cock, and I'm sure he'd absolutely love you too. Have you ever had a cock before? I should have asked you beforehand shouldn't I?"

"No, I haven't. I've not even touched one. Scared I guess and to be honest I'm not even sure if I'm bi."

"Well, there is one way to find out isn't there?" she replied, and so we talked some more and eventually I left, feeling very wobbly in the legs department, but seriously warm, cosy, satisfied and feminine. In fact, I felt like a woman as I drove away.

We agreed to meet again and she said she would call me.


Two days later and Cindy has already called me, despite us suggesting a monthly meeting. But I have to say I feel guilty that the whole meeting was more about me than her. Maybe this is my male side coming out.

So eventually I have another date set with Cindy (after having to cancel our last meeting due to a business trip I had to make at short notice), and I am pretty sure she has invited her male friend along. She denies it but I sense she is hiding something. I am not sure whether to go; just tell her if he shows up I'll leave; or quite what to do. Obviously, like many TGirls, I have fantasised about being with a guy but never had any intention to actually try it. I am not a brave soul, but I don't want to lose my relationship with her as it is so liberating. Why is life so complicated as a TGirl?

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