Jaime's Journey

Dave pulled out of my ass and came around in front of me.

"Girl, you ought to lick it clean."

I was appalled, then Susan spoke up.

"I kiss those lips. I'm not kissing shit. You want it clean, go to the bathroom and wash it off."

Dave looked disappointed and sat down as Mike positioned himself behind me.

"If you're going to be that way, then I get another pass at that ass."

"Whatever. She's not sucking your dick after it's been in her ass."

Mike fucked my ass, then Dave fucked me again, then Mike once more. Finally they seemed satisfied. I kind of curled up in a ball naked, sitting up on the bed. Dave and Mike put their clothes back on.

"Good night, girls. We'll see you again next week."

"Next week?"

"Bitch. You want us to keep quiet, then you can put out."

They left and Susan locked the door behind them. She came over and sat next to me on the bed and held me in her arms. She rocked me back and forth for a while, until I relaxed, then gently and sweetly made love to me. No more ass action that night. My ass had already had a workout. But she stroked my body, caressed my boobs, then took my little dick up into her pussy and I fucked her, before we curled up together and went to sleep.

I was nervous at work on Monday, but no one seemed to act any different, except Dave and Mike who occasionally leered at me. Dave came by leaned over and whispered quietly in my ear.

"See you Friday night, babe. I'm looking forward to it."

The next two Friday nights were a replay of the first one, with Dave and Mike getting sucked off then fucking my ass a couple of times. The terrible thing was, I was getting off on it physically, even though I hated it emotionally. After that third week, Susan and I were lying in bed together.

"You know there is one way to get rid of them and end this."

"How do we do that?"

"The only thing they have against you is photos of you partying, dressed as a woman. We tell HR that you are transitioning to a woman and will be dressing that way at work. You dress as a woman at work, and they don't have anything over you anymore."

"Go to work dressed as a woman?"

"What's worse, fucking the two of them every week, or dressing as a woman at work?"

"I don't care for either choice, but I'll go to work as a woman, if it means I don't have to fuck them again."

"That's my girl."

We talked to HR on Monday, and starting Tuesday, I came to work dressed as a woman. Dave and Mike were puzzled, then angry when Susan told them they could find someone else to fuck over. I'd been going to bars and clubs dressed this way, so it wasn't much different going to work this way. Most of the women seemed happy for me and I had no problems using the women's restroom.

Everything seemed to settle back down, and Susan and I seemed happy and loving together at home and going out together. As time passed, I found it became difficult for me to get a hard on, or to keep it long enough to fuck Susan. I was disappointed but we did still have a sex life. Finally Susan decided to address the issue.

"You know, that thing isn't doing you or me any good as it is."

"So what do we do?"

"Change it out. Have surgery. Switch from a useless dick to a pussy that we could both use."

"You want me to get rid of my dick and get a pussy?"

"Why not? You dress as a woman. You live as a woman. You can't make love like a man anymore. Get a pussy that we can both enjoy."

"I don't know if I'm ready for that."

"We've been together for awhile now. Do this and after you're healed, we'll get married. And I'd rather be with a woman with a pussy that works, than someone with a dick that doesn't."

"Married? After?"

"After. You got accumulated vacation for the surgery, and I've got vacation to be able to take care of you while you're recovering. And I swear, I'll never ask you for anything more that you're uncomfortable with."

Of course, she had already been checking out doctors. We scheduled it and the two of us went together. Susan held my hand as I went under, and was holding my hand as I woke up. Even with the drugs, it hurt like hell down there. It took two days before they took out the packing. After they did, they told me about dilating my new vagina.

I had to start out dilating it four times a day to keep it stretched out properly, and it hurt like hell doing it. Dilation is essentially taking a dildo, lubing it and sticking it in my vagina. The tissues there had been totally reworked and were recovering from that, which is why everything hurt so much. It felt weird thinking in terms of having a vagina. No, my dick had been largely non-functional, but it was still a dick.

Susan was with me most of the time during recovery, comforting me, kissing me, and caring for me. I hated the dilation, but Susan and the doctor told me it was necessary, so I kept at it. It happened slowly enough that I didn't notice it but slowly, it quit hurting as I dilated. What shocked me was the day I stuck my dilator in and it felt good for the first time.

I took it slow and easy -- I didn't want to mess anything up. I eased the dilator in and out of my pussy, and instead of the pain I once felt, I now felt pleasure. I began rocking my hips back and forth as I slowly and gently fucked myself with the dilator, until I leaned back, arched my back and had a full on orgasm, like nothing I'd ever felt before.

Susan was out running errands when all that happened, but I told her when she returned. She kissed me very sweetly and told me that while we still needed to take it easy, we could now start to have some fun.

We both returned to work shortly after that. I still had to take it easy and walked for exercise and to stretch all those things out. At work, some of the women hugged and kissed me. Yeah, there were a few who were cold, but that always happens.

We made plans for a small wedding and Susan and I went out shopping for wedding dresses. I wore a lacy white dress, which came down just below the knees, while Susan wore a silky white dress. I remember looking in the mirror at how I looked, which was marvelous, but then thinking back to the nerdy guy I'd once been. I'd gained something, but I shed a tear over what I'd lost on the way.

Looking back, I know that Susan had this all planned from the beginning. She picked a guy who would be so grateful for her love and affection that he wouldn't balk at the slow steady small changes. By the time the changes became material, I was so far along, it was almost impossible to go back. It is done. I am who I am now, and I am hers and she is mine. The Jaime I was before is dead. Jaime, the girl, is carrying on as best she can.