Lynn Begins to Transition, Ch. 01-02

Chapter One.

It has been nearly a year since my last update, which I regret, but once you learn about what has happened over the year I think you'll forgive me, if not at least understand why it took so long for me to set pen to paper and recount it all to you. Last summer, my wife and I split up. She thinks I left her for another woman, and I didn't disabuse her of that notion, seeing as I left her for Lynn.

It wasn't long after our visit to her gynecologist Dr. Sprague that Lynn and I went out to dinner on a date. I picked her up just before sunset. She was wearing a very pretty black dress, cut low in the front, no doubt for my benefit. She was wearing a push-up bra which gave her very small breasts just a bit of cleavage and since the bra was heavily padded, made them and her irresistible. After holding the car door for her and settling back into the driver's side, I looked over to her and kissed her.

"What was that for?" she asked,

"Your loveliness, of course," I smiled, "It isn't every day that a guy gets to go out on a date with a pretty girl." Lynn gleamed at the complement.

"Where are you taking me tonight?" she asked.

"Well, that depends on what you mean by 'taking' you" I replied with the corniest of responses, which of course made her blush. I loved that about her.

"I thought we'd go downtown to where we first met."

"Oh, I've wanted to go back there ever since then," she replied, "I love the Punch Room. It will always mean so much to me."

Lynn and I started our journey together in January of last year, meeting at the Punch Room Bar of the Ritz Carlton in downtown Charlotte. We had been chatting online for months before she summoned up the courage to actually meet in person. She didn't cross-dress in public then, appearing gender-fluid, but in the year and a half since had become braver and more confident in her femininity. And the hormone treatments Dr. Sprague's endocrinologist had started her on about six months earlier were making a remarkable difference in both her physical appearance and her self-awareness as the blossoming woman she was becoming.

"I do want to have a talk with you Lynn," I said, "and wanted a romantic, quite place."

"Uh-oh," she looked at me, "Sounds ominous."

"Ha!" I laughed, "Hardly that, darling, and you know that I love you!"

I was sure that set her mind at ease as we chatted all the way into the city. She was just a delight to be with, which I had recognized a few months back. We had declared our love for each other then and I had sensed that eventually we'd end up together.

We arrived at the Ritz Carlton about a half-hour after I had picked her up and took advantage of the valet service. I had checked into the hotel earlier that day, so the valets already knew the car and me. I pulled up into the valet area where the nattily dressed young man opened the door for her as I got out on my own. I could tell she was making an impression on him. It's a guy thing.

"Will you be needing the car again tonight, Mr. Roberts?" he asked with just a hint of a knowing smile.

"No, thank you," I told him and with a touch of double-entendre, "She'll be in good hands."

We took the elevator up to the fifteenth floor, just passing the floor my room was on. The elevator door opened, and we stepped into the bar.

"Good evening, Mr. Roberts," the maître d' greeted us, "right this way."

He led us, Lynn following him then me, to a small, corner table where we sat down and settled in. It didn't take long for our waiter to come by with the menus.

"Something to drink this evening, ma'am?" he asked Lynn.

"Oooooh, I don't know?" she said, looking at me.

"She'll have an Espresso Martini, and I'd like a Zubrowka Martini, up with a twist."

"Of course, sir" the waiter acknowledged my order and left us.

"I hope the coffee doesn't keep me awake tonight, Jim" she whispered.

"On the contrary, Lynn, I hope it does." I said with a wink.

As we continued our small talk, she would occasionally take her toe and rub it on one of my calves as women in love tend to do with their lover. Our drinks came right away, and the waiter left us with the menus to ponder.

"You were so serious back in the car at first, Jim" she said looking at me as she took the first sip of her drink, "Oh, this is really good."

"Good. I thought you might like it," I said to her as I leaned in, "Listen, Lynn, my wife and I are splitting up. She had been suspecting another woman, and she of course was right. I wanted you to know right away."

"Oh, so I'm 'the other woman'?" she asked quietly, "They don't teach that at Transition School."

"I've moved out and I think I've found a condo. Near here, in fact. I wanted you to see it first."

"Hmmmm."

"Meaning?"

"Meaning I have something to tell you also, Jim."

"Which is?" Now it was my turn to swallow.

"Which is that Teri is not happy that I've begun HRT and my beginning my transition."

"Oh?" Lynn's wife had been somewhat accustomed to her relationship with me, even cuckolding Lynn with me. I guess not anymore.

"She wants to be married to a man, she says, 'a real man' she said, and...," she faded off and peered down at her drink.

"And what, Lynn?" I asked as I lifted her chin back up to look at me.

"And I want to be married to a real man too," she said looking at me as tears welt up in her eyes.

"Ah ha," I said smiling at her, "Could it be that we could live happily ever after, Lynn?"

"I was hoping so, sir" she replied.

With the back of her fingertip, she lifted a teardrop that had dripped on her cheekbone. "These damned hormones!" she said with a little laugh. That broke the tension between us and we laughed quietly together, each understanding that our future together was beginning that evening.

The waiter came by, and we ordered our dinner, a bouillabaisse for two, and although I normally like a nice light burgundy with fish stew, it seemed appropriate to have champagne.

"And to drink, sir?" he asked.

"The 2012 Taittinger Comte de Champagne, please," I responded.

"Of course, sir" he replied, "Excellent."

"Oh, Jim" she looked at me reassured in herself and us.

As we waited for the wine to arrive, we continued our conversation. "There was something else, actually," she said.

"Oh? What possibly could that be? What could possibly top what you just told me?" I asked, quite honestly.

"I've been talking to Dr. Sprague, and I think I want to help out the hormones by getting an orchie," she replied, "I don't need them anymore and she said I wouldn't need any more bottom surgery if I didn't want to."

We had talked about this before. One of our "couple" friends had recently had it done and in fact should be well-healed by now.

"Wow, Lynn, you know I agree with your decision," she immediately started to correct me, "Our decision, and you know how much I love your clittie..."

"Even though you keep her locked up?" She interrupted me a second time.

"Especially because I keep her locked up, silly girl," I corrected her, feeling the small key to her chastity device that hung around my neck.

"Dr. Sprague said that after they remove... them... she could leave the skin loose or tighten it up depending on if I wanted the full bottom surgery in the future or not."

"I tell you what, let me text Jennifer and see if we can stop by their house. Would you like that?"

"Oh, yes please, Jim."

I don't like to text at dinner, especially with a pretty woman, but I could sense Lynn was anxious. I texted the woman who had recommended Dr. Sprague. She was one of the first people Lynn had confided in, and Lynn and I had also played once with her and her MtF girlfriend Jacey, formerly Jason, who had recently had the same surgery.

Big news to tell you. How goes Jacey's healing? You free tomorrow?

Barely a scar. She can't wait to show it off! After 2 works for us... What's the big news?

Tell you then. I texted, preferring to break the big news in person.

"Well, that settles it. Perfect! We'll check out my new apartment in the morning and go over to their house after lunch," I said to Lynn.

The waiter came by the champagne bucket, the bottle, and our flutes. When he uncorked the wine, the pop elicited the usual glances from a few of the other guests, but all they saw was a gentleman with a younger lady in a black dress, and I was fine with that, for it was true.

"We'll never compromise, Lynn, and we'll always be together." I said as I lifted my glass to her. She, in turn, mouthed "I love you," and smiled back at me.

Chapter Two.

We finished our meal. The bouillabaisse was terrific and the wine even better. Lynn had asked for a soufflé for dessert (two spoons) and I had a cup of coffee with two Grand Marniers, neat. It was approaching ten o'clock by the time we left the restaurant and went down the elevator to my room, two snifters in hand.

"I remember doing this before," she told me as we walked to the room.

"I distinctly remember the lock on your cage making a jiggling noise," I told her as she giggled, "But this time you're in a dress, aren't you?"

"I know. I remember that too. I thought the world could hear it!"

We arrived at the room where I opened the door and let her enter first, of course.

"Teri knows I'm seeing you tonight. I think she's happy I've found someone who lets me be myself, although she's not happy who I've become though."

"I get it, Lynn. Come here," I said as I set down the snifters full of the liqueur on the side table.

The door had closed behind us, leaving us alone to the world. I took her in my arms and embraced her with all the passion due her. She deserved to be loved as a woman, and god knows I did. I took her face in my hands and kissed it all over, finally settling on her mouth. Our tongues played with each other, mine probing hers inside her mouth, previewing what was to come later.

I reached behind her and unzipped her dress, then unclasped the hooks on the back of her bra, so that when she leaned back away from me (still kissing) I was able to take both off at the same time. She was exposed now. I broke the kiss and looked at her breasts.

"Oh god, Lynn," I exclaimed, "Look at your breasts!"

In the months since she began hormone treatments she had begun to develop as a woman, now clearly well into the breast bud stage. I could clearly see the elevation of her breasts above her chest and the enlargement of her areolae.

"Dr. Sprague tells me I'm at Tanner stage two, but boy do my nipples ache."

I leaned over and took one into my mouth while very gently caressing the other.

"Ooooooh, that's better already" she moaned, "It's been a while since you've seen them, and I didn't know if you'd be disappointed."

I released the nipple from my mouth and reassured her "Oh Lynn, how could I have been? You sound like you're talking to your bestie."

"Well, I guess I am, aren't I? Do you see any difference in my hips?"

Gently releasing the nipples from my fingertips, I lowered my hands down to them. "You know, I do!" I said, honestly, in fact. "Of course, I'll be able to tell better when you present to me as I mount you. Would that be okay?"

"I was hoping you'd say that sir," she smiled back at me as she kissed me again, this time more urgently.

Since we'd just finished a full meal, I didn't want her to try and service me orally, as much as she may have wanted. Most experienced cocksuckers prefer to make love to a cock on an empty stomach, and Lynn was by no means an experienced cocksucker. A deliciously enthusiastic one yes, but not experienced.

"Let's get these panties off, shall we?" I told her as I slipped her completely out of her dress and removed the black lace panties, leaving her naked save the garter belt and stockings and her cage, of course.

She was exquisite. I reached around my neck and removed the key to the chastity cage that held her clit tantalizingly out of her touch. I unlocked it and slipped the cage and its urethral tube off and out of her, then the ring around her testes that had held the cage in place. Since she had been fitted for it, I rarely allowed her to remove it, especially as I had the only key. Once it was free, the clit began to swell immediately so naturally, I enwombed it with my mouth.

She clearly delighted in the freedom from the cage as the clit swelled within my mouth, my tongue stroking across its shaft. Though I was an experienced cocksucker, I knew I could take her entirely in my mouth even on a full stomach. I cupped her ball sac, still containing the doomed testes as I treated her to a suckling to make up for the weeks she'd been encased.

Lynn leaks profusely, so I was soon rewarded with a tasty pre-cum. I knew she hadn't orgasmed in a while, so she wouldn't take long. Without breaking rhythm in my sucking, I reached up to her mouth with two fingers extended. She knew what I wanted as she licked them, getting them as wet with her saliva as she could, for she knew where they were going.

When she was done wetting them, I took the fingers and pressed one, then the other, into her rear passage. They met no resistance. I pushed deep into her, finding the walnut-sized gland I was feeling for. This set her off, and she pumped three goodly jets of Lynnseed into my mouth. This precious fluid I craved not only because it meant sexual release for her, but also because I loved the taste! It was essentially without flavor yet tasted "thick." Because she hadn't cum in so long, there was indeed plenty of Lynnseed for me to enjoy. She is younger than I and still can produce quite a mouthful when sufficiently aroused. The poor girl is often subjected to an hour or more of edging for no other reason than that.

"Oh god Jim, thank you" she gasped when she was able to catch her breath, still holding onto my head from above. I kept the clittie in my mouth as it went soft, continuing to drip the last of her Lynnseed into the warm wet chamber of my mouth. "Mmmm-hmmm" I mumbled, looking up at her. I swallowed the mixture of Lynnseed and my saliva, swallowed around the clit even as it remained softening in my mouth. I do so love doing that.

When I was sure she was fully sated, I withdrew it from my mouth, kissing the tip, and licking the narrow slit still tender from the urethral tube of the chastity cage. Standing up, we kissed and embraced tightly. She could feel my solidly erect man-cock even as it pressed against her softened clit.

She broke the kiss and asked, "Would you please check my hip development now, sir?" as she laid face and breasts down on the bed in front of her.

"Hah! Indeed, I will indeed!" I said as I went over to the nightstand and took the KY warming gel and slathered it onto my cock and between her pretty bum cheeks. Her saliva might have been sufficient lubricant for a finger or two, but not for a cock of my girth and it was not pain I was after, but rather our mutual pleasure.

After tossing the lube aside I aligned my cockhead at the entrance of her most intimate of places and placed both hands on either side of her hips. Hips that still wore the black garter and kept her stockings still in place high over her thighs.

"You know, I think I can feel your hips..." I said as I plunged deeply and firmly into her to the root.

"Ohhhhh shhhhh" she moaned into the pillow as she took it in.

"That's a good gurl," I told her softly, "Take your man. It's your cock, you know, given to you freely and lovingly for your pleasure."

"Oh, my goodness" she implored, "Let me... just wait, just a sec" as she tried to adjust to the man-cock that was impaling her. She had received it before, of course, but I don't recall ever giving it to her so hard without letting her adapt to it. Yet never had I loved her so. I waited for her.

"Okay, good, I'm ready now" she said as she reached back with one hand and touched one of my hands that held her hips. Hips that had, in fact, widened perceptively since beginning estrogen. We had talked about how as a transitioning gurl, her sex organ really had been transitioning from her cock, becoming in essence more of a clitoris full of nerves, to her rear passage, now her pussy. Soon, with the orchiectomy, the transition would be complete.

I began to take her in earnest now, probing deeply into her, not just thrusting in one direction (inward) but trying to rub her pussy walls differently with each few strokes, always ending each thrust on the prostate deep inside her. Even after such a powerful orgasm a few minutes earlier, her clit soon began to leak onto the edge of the bed.

It didn't take me long to cum. The blowjob I had just given her and the expressions of love we gave each other all evening had aroused me such that I jetted into her sooner than I normally did. But it was a delicious orgasm nevertheless. I pressed hard into her as I came, releasing her hips and reaching up and under her to grasp her small breasts. I couldn't get any deeper into her. The cock was into her pussy to its root, I could feel her prostate through the lining of her pussy and rubbed against it with my cockhead.

"Mmmmmmmmm" she moaned, "I can feel it, the cum, the warmth, the love."

I lifted her onto the bed all the way, and as I grew soft still inside of her, we fell asleep, knowing we had found our future.