It only took a month the see a subtle change. Two months in, I really started to feel it. It had been years since I didn't have a regular workout routine but in an effort to show Brad how committed I was to him, I was all in on role-playing my pregnancy. Not only was I feeling the additional weight I had put on, but it was noticeable to my family and friends. I blamed the lack of working out on a nagging back injury. I wrote off my drastic change in eating habits to stress from work. In just over two months I had gained twenty-three pounds. I knew I was on the right track when my brother sarcastically validated my effort.

"Dude, if you gain any more weight, people are going to think you're pregnant."

Mission accomplished.

Brad noticed the change as well and on each of his visits, he played his role of expectant father extremely well. As sexual as we remained, he also became much more nurturing and supportive. He knew this was killing me. Three months and thirty-one pounds into my experience, I anxiously made my way to his hotel room as I always did when he arrived to find that sexy lingerie had been replaced by very comfortable by stylish looking maternity ware. I held it up and looked at myself in the mirror.

"As long as he loved me," I thought to myself.

Brad returned from his meetings to find me doing my nails in a bra and panties.

"Do you know how much I love you?" he asked.

"Are you just saying that or do you really love me?"

He sat down next to me and kissed me, rubbing my fat belly as he did.

"What would you say if I suggested we go on a vacation together? I have a conference in Florida next month and I was thinking about getting us a nice exclusive beachfront condo right on the ocean."

"I'd say I'd be really interested if you told me you were leaving your wife, but I assume this is the part where you share with me that she can't make it so why not bring me instead?"

His silence proved I knew him all too well.

"Listen, I really don't fucking care why. But yeah, I'm in. What the fuck. Let me ask you a question though. What if I told you I wanted to start transitioning to be a girl full time? Do you ever think there would really be an 'us'?"

And now, I caught him off guard.

"That's an interesting proposition. We've never really talked about that before," Brad responded as he relaxed on the couch.

"I've been thinking about this a lot lately. I never thought I would want to transition and give up being a man. I'm sure there are steps and a process. I'm just saying I would think about it if I knew I had the right person to support me."

"But sweetie, you would be giving up everything. What would your family say? And would you change everything? I kind of like your cock," Brad responded, sliding his hands between my thighs, rubbing my cock softly over the satin panties I was wearing.

"I don't know. I'll tell you what I do want though," I said as I put down the jar of nail polish and moved the coffee table away.

Brad started to loosen his belt as I got on my knees in front of him. I could see his cock start to get hard as I worked his pants off over his feet. As I pulled down his briefs, his cock sprang out. I loved the fact that he got so turned on, so quickly. I took it in my hand and slowly started to stroke it. He leaned back on the couch.

I slowly took his cock in my mouth. First, the tip, and then I attached my lips to his shaft. My lips slowly made their way to the bottom. I paused for a moment, gagging slightly as I did, and then worked my lips and tongue back to the head. I licked down the side toward his balls. I loved sucking on his nuts. I played with them in my hand for a moment, kissed them softy, and then took both of them in my mouth at once. I loved how smooth they felt against my tongue. I licked both of them, continuing to stroke his cock as I did. As much as I would always lose myself in the moment, I loved watching as Brad worked up to his orgasm. He would always tell me how much better I sucked his cock than his wife. I was in the mood to hear it again.

I took my mouth off his balls for a moment and asked, "Who is the best cock sucker you know?"

"You know you are," he said without hesitation.

"I'm even better than your wife?"

"Of course you are."

I smiled as I took all of his cock again. It wouldn't take him long to cum and I would get the pleasure of swallowing all of his sweet jizz. I could feel myself getting hard just thinking about his cum filling my mouth. I started to quicken the pace of my mouth and lips on his cock. I could feel him getting harder. My mind wandered to the sensation of him sticking his dick in my dripping wet pussy and fucking me uncontrollably. I felt Brad's hands move in behind my head pushing my mouth down further on his cock, fucking my mouth as his hips slapped against my face. As much as I loved his sweet side, I loved aggressive Brad even more.

It was a second later that I felt the first shot of cum hit the roof of my mouth, followed by a steady stream that very quickly filled me up. I slowly swallowed it all, savoring the taste and licking my lips clean. Brad fell back onto the couch. I sat down next to him and grabbed my nail polish to finish the last few toenails that needed paint.

Brad's three-day stay was filled with plenty of pampering, a lot of great sex, and more than a few conversations about how different things would be if I were a girl. The final night included a trip to a very nice restaurant with a very private table. I was wearing the black velvet jumpsuit he had bought me that really accentuated my large belly. The feeling of the soft fabric rubbing against my skin felt so nice. I was drawing smiles from other women sitting and having dinner. The hostess, an attractive woman in her forties, whispered in my ear as I sat down.

"You look stunning. Congratulations."

It took a moment for me to take in that compliment before I thanked her. Alone with Brad, I asked him if I ever told him how I started crossdressing. He didn't think I did. I shared the story of that night in Missy's room, being dressed like a cute sixteen-year-old who went from being a buddy to a babe, and how I would never forget how I felt that night. I never imagined it would have progressed to where I was today.

"Did you have sex with any of your friends that night?" Brad asked.

"Not that night but looking back, I would have loved to give them head like I give you," I said with a wink. "And I admit, I certainly thought about what it would be like to have sex with a few of them. I was just so unsure of myself and who I was back then."

"I bet you were adorable," he said as he started looking over the menu. "And sexy."

"The one thing I always thought about was how it would be if I had real boobs. I used to fantasize about giving my friends blowjobs and them feeling me up, sucking on my nipples. It's the one part of me that I've always been very conscious of."

I looked down at my menu. There was a moment of silence.

"What would you say if I told you I wanted a boob job?" I asked subtly.

"It's funny you say that because I've noticed how much fuller you're boobs have become over the past few months. I love them and yes, you should really think about it," Brad answered in a very matter-of-fact, enthusiastic manner. "I mean it's a big change but if you ever wanted to think about starting a transition maybe just adding one thing might be a good start."

I was a little speechless so I figure I'd look back at the menu.

"And I'll pay for it," he added.

Now I was really speechless.

"I don't think they should be too big, you know? But something you can show off. Maybe a perky B-Cup? The more I think about it, I think it is definitely something you should consider," he said. Clearly, he had put a little thought into this since I had mentioned it.

"Well ok, let's talk about it. And thank you."

Dinner was delightful. I was sneaking sips of wine out of Brad's glass most of the night so by the time we were finished and back at the hotel, I was horny as fuck for him. It didn't take long for him to have me mounted doggie style on our bed, thrusting his perfect cock inside me. It was just minutes before I felt stream after stream of cum filling me up from behind. He turned me over and put his still hard cock back inside me.

"I wish I knew you when you were sixteen. I bet you were a cute little thing weren't you?" he asked as he thrust his cock deep inside me.

"I definitely would have fucked you!" I replied.

"Fuck! I wish I was there. Tight little pussy for me. Little perky tits. I can just imagine how cute you were," he said thrusting harder inside of me.

I lost was lost in it all. I was flashing back to that day in Missy's room. Coming out of her room in that short black sweater dress and gym shoes feeling like a cute little teenage girl. But feeling like a slut wanting cock inside me. I imagined Brad seeing me, feeling me up under my dress, reaching under my panties and fingering my tight virgin hole. With every thrust, I think about what it would have felt like to have a man's cock buried deep inside me and how much more I would have craved cock.

I felt Brad's hands reach under and behind me to unclasp my bra. His hands engulfed my swelled breasts before attaching his lips to one of my nipples. Each thrust of Brad's cock felt deeper inside of me. My cock was as hard as a rock as well and could feel it rubbing against Brad as fucked me. Brad groped my breasts and rubbed my enormous belly while fucking me harder and harder. I started stroking my own cock.

"You little pregnant slut! You little whore!" he screamed at me.

His groping stopped for a moment for him to gently rub my belly and look down at me with lustful eyes.

"Fuck! You're so fucking incredible! I love your tight pussy. I love cumming inside you."

I watched as pre-sum started dribbling out of the tip of my cock followed shortly thereafter by streams of white jizz which shot up onto my belly. Brad rubbed it all over my body before laying on top of me, thrusting even harder inside me. It was only a minute later that I felt him filling me up again with wave after wave of his cum, both of us screaming in sexual delight as he did. A moment after he stopped, he slid his cock out of me and lay next to me on the bed.

"I love you Jenni" were the last words he whispered before we both fell asleep, sexually, emotionally, and physically exhausted from the day.

I remember Brad waking up early the next morning for a meeting and telling me he had to fly home unexpectedly that day, rather than the next as he had planned. He kissed me on my forehead as he left. He had scheduled a wake-up call for me for around nine that morning which gave me enough time to shower and depart. Driving home my mind wandered. This had become very real and I struggled with figuring out what was next.

I was at odds with myself. I thought over and over about what my life could be and what I wanted it to be. My family and I were at odds. My dad had found a bra and panties in one of my drawers and questioned me to no end if they were mine. Had he looked a little harder, he would have had a lot more questions to ask. But like my alternative life, my clothes, shoes, makeup, and sexy lingerie were all very well hidden. It was time to decide if Jenni should be a bigger and more visible part of my life.