Brad and I had been seeing each other for over a year when he would come into town. Our meetings started in his hotel suite and progressed over the months to restaurants, walks around town, and trips out shopping. Brad was extremely well off, successful, and more than generous when it came to gifts. In bed, our relationship was fantastic. Brad was a marvelous kisser and loved foreplay. As many sexual experiences that he and I had, there were equally as many nights of simply enjoying each other’s company. When he would leave, it would take me days to recoil back into everyday life. It became even more difficult with time when I realized that I, as Jenni, was completely falling in love with this married man.

When Brad was at home in Maryland, it was common for us to have two or three online chats a week. Much like our time together, there were some nights that were tame, adult-like conversations. There were others that were scorching hot and unbelievably orgasmic. He claimed I was the first person to ever get him aroused over the phone and make him cum. These late night online sessions would typically lead to phone sex with some type of role play that would lead to both of us sharing an orgasm before logging off and going to bed.

One night started like any other night. Brad had mentioned having to get up early the next morning and that our online session would need to be short. As we playfully bantered back and forth, he asked me what was one thing that I wished I could do with him that we might never think was possible. I thought about my answer for a moment before replying that I would love to have a baby with him. I chuckled a little as I hit send and waited to see his response. There was no response. Moments later he left our private chat room.

He and I didn't chat again for another week. I was certain that I had pressed the wrong button with the "have your baby" line and that the next chat, if any, was going to be to end things. I had convinced myself all week that this was going to be the result and that my relationship with Brad was over. I was depressed. Every night I would log online only to find that Brad had not. A week later, he was in our room waiting for me when I logged on. He explained he was a little spooked when my reply was exactly what he was thinking. He continued that the sudden realization he was having an affair with a man who dressed as a woman slapped him hard across the face. Role playing had become real and his feelings for me had overwhelmed him. I wasn't sure how to respond. What was a completely open and fun relationship had become very awkward, very quickly. He asked if he could call.

"Jenni, I am so sorry babe."

It sounded very much like a breakup call. Brad continued.

"I should have connected with you earlier in the week. I didn't and that's on me. As spooked as I was for a minute or two, or maybe longer, I want to ask you an honest question. How serious were you about what you said?"

"Brad, I'm not a girl. I can't have a baby. Clearly there is an issue here and that's cool. Let's just move on."

"Jenni, obviously I know that you're not a girl, but you know I think you look great. You've got a smoking body. You're an incredible lover. But would you ever consider role playing what you said you wanted?"

"OK, so you're on the right track with these compliments," I said coyly. "But what do you even mean about role playing? Role playing being pregnant?" I asked. "Brad, that would probably be a little difficult."

My mouth was saying one thing, but my mind was racing with thoughts and ideas on how I could pull this off. First, I wanted to hear what he had to say.

"I know it seems crazy but what if there was a way? I think we should consider it. The image of you with a pregnant belly. I can’t get it out of my head. I imagine we could come up with something that we would both enjoy. Especially the 'getting pregnant' part at least."

We decided we would both think about it, and I decided that I would forgive him as long as he bought me some new lingerie the next time he came into town. He agreed. He would be back in town for two nights next week. He said he would make it up to me.

I always took extraordinary pride in staying fit and looking very athletic. The more I worked out and stayed active, the easier it was to find stylish clothing that fit my everyday image as well as having the ability to slide into something sexy when I wanted. I kept asking myself, if I let it go, could I get it back? The idea of having this big pregnant belly kept running through my head. Could I forego this look I worked so hard to achieve for a man? I convinced myself that if I was going to do this, I wanted to commit to it one hundred percent.

I arrived at the hotel room right before Brad was leaving for a meeting. He pulled me close to him, told me how much he missed me, and kissed me like he damn sure meant it. His lips against mine turned me on. His tongue and my tongue meeting turned me on. I reached between his legs and felt his cock getting hard.

"I have to go babe. Make yourself at home as you always do. I'll be back as soon as I can."

I rubbed both my hands on his chest and asked, "Are those for me?" motioning to the two boxes on the bed.

"They are for you. For later. I'll be back."

He gave me one last kiss and was out the door. I went and opened box number one and found a ridiculously cute black dress. He had told me to bring my favorite black boots so maybe we were heading out. I opened box number two and found what I was really looking for. Brad knew that black lace was my favorite and he hit a home run with a matching bra, panty, and garter set along with some sexy black sheer stockings. I knew what I'd be wearing when he got back to the room for sure.

I spent the day pampering and preparing myself for Brad's return. I had selected a shorter length black wig with bangs, a style I knew was a favorite for our time together. I had a light lunch before opening a bottle of champagne he had left to chill. By two in the afternoon, I knew he could be back at any minute. Since the black dress could always slide into place, I decided that the lingerie and boots would be an appropriate "welcome home" for Brad when he arrived. I was two glasses of champagne into the afternoon when he returned.

Brad dropped his bag on the floor, tossed his keys on the counter, and called out for me. I walked from the master suite through a set of doors that separated the two rooms. He walked toward me, we met, and we began to kiss. After at least five minutes of locking lips, he took a step back to admire me.

"You are so fucking incredible. You turn me on just standing there and drive me crazy when we touch."

"I'm sure I'm blushing. I'm just glad you like it. I feel so incredibly sexy. Thank you."

"Sexy doesn't even start to describe you. Fuck."

I decided no better time to break the ice.

"But would you still love me if I were fat and pregnant?" I asked with a soft smile.

"Oh boy. I was wondering if that was going to come up. I am so sorry for putting you on the spot like I did. Honestly though, I can't take my mind off of the thought of you carrying my child. I mean, I know it would be a fantasy and all, but still."

"Well, I have been fantasizing about the same thing. I've really thought hard about it and I have an idea. But I want it to be a surprise. But if I'm being honest with you, if you only love me for my body, I think we're both going to be very disappointed."

"I'm beginning to think it would be very hard for you to disappoint me," he said as I loosened his tie and started to unbutton his shirt. I looked him in the eye.

"I love you Brad and I want to have your baby. I want you to cum inside me and show me that you want the same. Make love to me."

I finished removing his shirt while he undid his pants, letting them drop to the floor. His hard cock was pushing against the fabric of his underwear until I pulled them off, freeing his manhood. I dropped to my knees, immediately taking all his cock in my mouth, allowing my tongue to circle his shaft much to my delight. I briefly came up for air before taking it all again, this time allowing my exceptionally pouty lips to attach to his throbbing head and slowly move down, taking all his cock in my mouth and throat.

After ten minutes, his cock started to pulsate, a familiar indication that he was going to cum. After the first taste of precum, I moved my hands to his ass allowing him to put his hands on the back of my head. His thrusting became more pronounced as he fucked my mouth like it was a wet pussy. Moments later his sweet jizz started to flow, quickly filling my entire mouth with his creamy white semen. I swallowed every drop and licked him clean before standing up, continuing to stroke his cock with my hand as I did.

“Well then, what else do we have planned for today?” I asked.

Brad took my hand and led me to the bed. I looked into his eyes as he slowly ran his fingers down my shoulder and arm. His other hand reached behind and rubbed my ass.

“God, I love your body. I love the way you worship my cock.”

Brad stopped speaking and seemed conflicted.

“Brad, when I said ‘I love you’ I meant it. I have fallen completely in love with you. I imagine us together. I imagine becoming more of a woman for you than I am now. And when I said I would have your baby, I meant it.” I paused for a moment before continuing.

“I know it’s physically impossible, but I want you to fuck me like I was your wife. Your cock inside me. I want you to shoot all your hot cum inside me. I want to feel your cum inside me. In my mind, I will believe I’m having your baby. Physically and mentally, I will believe I am pregnant. It will be the most realistic role play we have ever had.”

We started to kiss, collapsing on the bed as we did. Brad’s hands started to explore my body. He had never openly tried to touch my cock, but his hand slowly slid into my panties, and I felt him softly hold it.

“I’ve wanted to touch you. I want to taste you.”

I pushed his head down toward my hard cock. He licked my chest and stomach before getting to my waist. He undid my garters and slowly slid my panties down my silk covered legs. He licked all around the base of my cock before sliding his tongue up from the bottom to my throbbing head. His lips on my cock felt incredible. I leaned back and moaned as he took my dick in his mouth.

I knew I couldn’t last long and after about three minutes I felt pre-cum at the tip. Moments later I started to cum. Much to my surprise, Brad took most of it in his mouth but did not swallow. Instead, he crawled back to me to kiss me, allowing me to enjoy and taste my own cum. I sucked it off his tongue and swallowed it all, much to my delight and his.

Brad’s cock was started to get hard, and I wanted to suck him off again. He had other plans. He turned me over on my stomach, telling me to give him my ass. I arched it upwards, giving him a sultry look of approval. He spat on my hole and quickly buried his head between my cheeks. His tongue licked my bud before he opened my cheeks allowing room for his tongue go to work.

Before long Brad inserted a finger, then two into my asshole. I looked back and saw the pure enjoyment he was having. I started to moan in delight, and his fingers started sliding in and out. Shortly after, he removed his fingers, and I felt the head of his cock ready to enter me. As he slowly inserted himself inside me, I realized he was not wearing a condom like he normally would.

“Baby,” I started before he quickly cut me off.

“I’m going to give you what you want. Me inside you. I’m going to fill you with my cum.”

Brad’s cock was now completely buried inside me as he moved against me, lying next to me on the bed.

“Fuck you feel so incredible. I love your tight little pussy. So you say you love me? How much? Are you willing to give yourself up for me? All of you? You want a baby? Are you ready to show me how bad do you really want this?”

“Fuck me right now!” I screamed in return.

I could feel his cock swelling inside of me, growing harder with each thrust. My screams became louder which each hard thrust inside me. Lying beside me on the bed, Brad’s left arm lay across my chest, squeezing my right breast, and pulling me tightly against him with each thrust. Brad's cock had been inside me before, but this was the first time without any protection. My mind concentrated on the feeling of his huge cock and soft flesh inside me. I had felt this feeling once before. When Tony had fucked me in college though, it was just that, a good fuck. He was forceful and angry. Brad and I were different. Tony was lust. Brad and I were love. We were starting down a road I wasn’t entirely even sure I was ready for.

With his cock buried deep inside me and after one final thrust, I felt the first of multiple waves of his cum start to fill me up. As his cum was filling me up, I felt his lips softly kiss the nape of my neck as his fingers played with my erect nipples under the black lace of my push up bra. I felt his cum inside me. I felt him pull me tightly against his body. I was in love Brad, and this was the first step in showing him just how much.