Jaime's Journey

She stopped with the dick in my ass, while I spurted all over the bed. She held onto my hips to keep it in there as I almost collapsed from the orgasm. Finally she let go and let me sink onto the bed as the strap-on eased its way back out of my ass. She rolled me on my side and lay down alongside me.

"Why do I think that someone who was reluctant enjoyed it a lot more than he thought he would?"

We began adding that to our regular fucking routine, and before long, when the strap-on was clean, she even had me sucking on it. I mean, I was still repelled at the thought of sucking or being fucked by a real dick, but I kind of got used to this.

After a few weeks, Susan came home with what appeared to be a pointed mushroom with a glass jewel on the end. It was a butt plug and she had two, one pink and one blue.

"You're mine and I'm yours. We don't have rings because we aren't married, but this is a way for us to show the link we have. I'll wear one and you wear the other."

How was I going to argue with her? Was it worth moving out and losing her? And kind of like the panties and shaving, how would anyone beside us ever know. Besides which at this point I was getting used to having her stick things in my ass. I took the blue one and she took the pink. She put mine in my ass, and I put hers in her ass.

Every time Susan asked me to do something weird like this, our fucking would be particularly intense and long lasting. She became a real sex machine in bed for days afterwards.

Susan said she had some pills that would help inhibit my body and facial hair, and she had me start taking them every day. Sure enough, I noticed I was getting less hair, particularly on my face, and the body hair was lighter and finer. After a few weeks, I noticed my nipples getting a lot more sensitive. The areolas seemed to get larger as well. I didn't understand and mentioned something to her.

When I took off my shirt, she ran her hands over my nipples and I felt almost electric shocks of pleasure. I know that doesn't make sense, but that's the only way I can describe it. She stroked my nipples as I just lay back and was astounded by the sensations. She then put her lips on one nipple and began sucking on it. I thought I was going to levitate off the bed. I couldn't have even imagined that having a woman touch and suck my nipples could feel so good. I didn't come like spurting, but I felt rolling waves of pleasure going through my body.

Needless to say,, we now had something new to add to our sex play. Later she told me she'd checked and found that was one of the side effects of the pills that inhibited hair. Only months later did I realize she'd lied to me. I was taking hormones that blocked male hormones and supplied female hormones. Before long, I began to grow boobs.

Susan dismissed that, saying lots of men had man-boobs. It was nothing unusual. Well, no it wasn't unusual for men taking hormones to transition to female. Before long I easily had a-cup boobs, and had to wear tight tee shirts to keep my boobs hidden at work. Every now and then someone would give me a funny look, but no one at work ever said anything.

One Friday night, we went home before going out.

"Jaime, dear. I was you to dress up extra special for me tonight. We aren't going out with the usual group. It'll just be you and me some place different."

"Okay. What do you want me to wear?"

"I'll find some things and dress you. Take off everything but your panties."

I undressed, with my little boobs kind of dangling, which embarrassed me. As she walked by, she stopped and kissed each boob in turn. She produced a bra which would not hold her boobs, but was the right size for mine.

"You want me to wear a bra in public?"

"Yes, I do. And you will wear it. Besides by the time I'm done no one will notice."

I put the bra on, though Susan had to help me fasten it. She then produced a pink pullover top and had me put it on. I was starting to get uneasy. She came up to me, stroked my body and kissed me.

"Trust me. When I'm done, no one will even recognize you as the Jaime I work with. Besides we're going some place where the other work folks don't go."

She put a skirt on me that didn't quite come to my knees. She then sat me down and painted my fingernails a bright red. She then plucked my eyebrows slightly to shape them, and made up my face. I sat there in shock as she did this. Base, eyeliner, eye shadow, lipstick -- if I looked like I was even going to protest, she put her finger to my lips to hush me. Finally she pulled a blonde wig out of her closet and put it on me.

"We've let your hair get a little longer, but it isn't quite long enough for this yet. Give it a couple of months, we'll get there."

Obviously she was saying she planned to do this again, probably more than once. I wanted to cry, but was almost numb. I couldn't find the tears, and besides it would have messed up my makeup and Susan would have been mad at me.

"Jaime is not only my special boy, you're also my special girl. I do love you so, and you know you'll get your reward later."

She put me in a pair of two inch wedge heels.

"You can't handle serious heels. We'll get there though."

I looked in the mirror and I didn't recognize me. I saw a pretty blonde girl, dressed to kill. Back in the day I'd have killed to get that girl -- now I was that girl.

Susan dressed and we went to a club we'd never been to before. It was way on the other side of town and almost hidden. We walked in and I didn't recognize a single person there, and was very relieved. As I looked about, I noticed that most of the guys were dancing with other guys, and most of the women danced with other women. Susan noticed my looking around, smiled, and stroked my head before kissing me.

"Don't worry honey. Most of the guys here won't have any interest in you -- at least as long as they think you're a girl. Just make sure if you go to the bathroom, to use the women's."

I hadn't even thought that far ahead, but realized I sure didn't want to walk in a men's room dressed like this. We found a table and got some drinks. We sipped our drinks, and with a little alcohol, I was starting to relax. A very masculine looking woman came over to our table.

"Hey, Suzie-Q. Haven't seen much of you for a while. Guess I know why now. You found yourself a new little squeeze."

"Hey, Jill. This is my girlfriend, Jaime."

"Damn girl. You better keep a tight hold on Jaime, or I'll steal her away from you."

"Go ahead and try. I'm not sure you'll get far."

"I... Susan and I live together."

"Got her locked down, huh. Have fun girls."

She laughed and walked off. I was surprised how many women came over and talked to us. I was even more surprised how many flirted with me. As a guy, no one even paid any attention to me. Now that I appeared to be a woman, half the women in this place seem to want me. I said something to Susan about it.

"You're fresh meat. They've never seen you before or slept with you and you're cute enough to catch their attention."

After we'd had a drink or two we got up and danced. We found ourselves in the middle of a bunch of women. Half the time I couldn't be completely sure who I was dancing with. A slow number came on and Susan slow danced with me. I let her lead. I'm not a good enough dancer to lead.

That number ended and another slow number came on and a gorgeous woman asked if she could cut in and grabbed me around the waist and danced with me. She snuggled close to me and ran her hand all over my ass while we danced. At the end of the number she gave me a passionate kiss and felt up my boobs. I turned to go back to Susan, and another woman grabbed me.

"Hey honey, dance with me."

"I have to get back to..."

"She can do without you for one more dance. Come on beautiful, dance with me."

This woman was groping me like nobody's business. My gaff was holding me very tight, otherwise she'd have felt my prick when her hand went down there. It almost felt like I was being sexually assaulted on the dance floor. The dance ended and she kissed me and groped me some more. I started to try to break free and she held on until Susan appeared.

"Okay, bitch. You've had your fun. Jaime's taken, so go find someone else."

The woman glared at Susan who stood her ground. Several other women and men gathered around. As they were facing off, a female bouncer grabbed the other woman's arm.

"Okay Charlotte. Go back and play with your friends. We aren't going to have any trouble here now, are we?"

Charlotte glared at the bouncer, then at Susan, and stomped off away from us. Susan and I went back to our table and got another drink. A little later, I saw Charlotte leave with another woman. Later on the bouncer came over to our table.

"Sorry about that. She gets really pushy after she's had too many drinks."

"That's okay. It was just that Jaime didn't know how to handle her."

The bouncer looked me over very carefully.

"Jaime, huh. She's trans, isn't she."

I didn't know what the hell she was talking about, but Susan obviously did.

"Just come out. Hasn't had bottom surgery though."

"You pass real well, honey."

"Tha... thanks."

"So is she going all the way?"

"Not for the time being. Still trying to decide her direction. You'll keep that on the downlow though, right?"

"Sure thing, Suze. Don't want to run off this pretty lady. I'd be half tempted to go for her, even knowing she's still got a package."

We left shortly after and went home. We had some of the wildest sex we'd had in weeks. After we were both exhausted from fucking, I asked what the bouncer had meant. Susan told me not to worry about it for now.

The next morning, I was going to clean off all the makeup and change to boy clothes. Susan asked me to stay that way and go to the mall with her. I felt really weird, but did it. She put me in another outfit and open toe flats. She touched up my makeup and we went out.

At the mall, there was a nail salon. Susan dragged me in there for a pedicure. They massaged my feet, cleaned off the callus, trimmed and shaped my toenails, then painted them. We gave it a little time to dry, then walked the mall and went clothes shopping. Susan bought me a few more girl outfits. I had to go in the women's dressing rooms to try on some of the clothes and once I'd done it a few times, it didn't even matter.

We had to pee, and Susan walked me into the women's restroom. I'd been in the women's room last night at the bar, but it felt different at the mall. I had to pee though, so I did it, washed my hands and left.

As we walked through the mall, a couple of young guys tried hitting up on us -- both Susan and me, and seemed every bit as interested in me as in Susan. Susan made some polite excuses and got us away from them. We were walking back to the car, when a guy in the parking lot yelled out to us.

"Hey, baby. I'd sure love to get my hands on that ass. You bet."

"Take it easy and just ignore him. He's trying to get a rise out of you."

We got in our car and drove off, and I'd swear I thought I saw that guy pass us in traffic a little later. We got back home and Susan suggested we go out again that night, with me still dressed as a woman.

"We won't go back to the same place as last night, but I think we'll be just fine."

At that point, I was almost becoming numb to how I was dressed. We showered, Susan redid my makeup and explained what she was doing and how as she did.

"Before long you'll be able to do your own makeup just fine."

"Please don't make me go to work this way. Please."

"No, I'm not going to do that. This is just for when you and I go out and take a walk on the wild side."

"I don't know how much wild I can handle."

We went to another bar, and while it didn't have the gay men and women of the other place, no one seemed to care about two women dancing together. We went home after and had more wild sex.

Monday morning, Susan helped me clean off my makeup and took the polish off my fingernails. I wanted her to take off the toenail polish but she refused.

"Jaime, dear, you aren't going to take off your shoes and socks at work. No one will know you have polish on your toenails. Besides it looks so pretty."

That kind of set the tone for how life went for a while. Susan dressed me up as a girl for out weekends, and I kept toenail polish on, just as I did my panties, butt plug, and gaff. Generally when we went out, Susan would tell any guys who approached us that we were on a girl's night and weren't looking for company. Usually that was enough to drive off most of them. Bouncers took care of the rest. We went back to the gay bar and hung with the lesbians pretty regularly, but not every weekend.

My boobs kept growing until I was a b-cup. I really had to work at it to hide them while at work. I started wearing a binder on my chest while I was there. In some ways I began to feel freer evenings and weekends when I could just wear a bra on them.

Frequently when we were out, guys would ask us to dance. Usually Susan would decline, but once in a while she'd suggest we just dance with the guys for a dance or two, just to make it easier to get rid of them. Fast dances were great, but particularly at first, I was uncomfortable slow dancing with a guy. I did it to make Susan happy, because she did plenty of things to make me happy.

One night we were at a club, and during a slow dance, the guy was groping me and feeling me up all over. He grabbed my ass, my boobs, and even down over my groin. Thank God for my gaff that made my dick disappear. Susan told me how angry guys might get if they found I had a dick. At the end of the dance, he kissed me and continued to grope me until I could break away from him.

I went over to the table where Susan stood with two other guys. I'd had a bit to drink and was still reeling from the assault on the dance floor. As I walked up, one of them turned to me.

"Damn. That was a hell of a show on the dance floor. I almost didn't recognize you, Jaime."

I realized the two guys were Dave and Mike from work. I was shocked and scared. No one from work, except Susan, of course, knew I dressed this way at times. And I was doing it for Susan, not because I particularly wanted to, even though I was enjoying it. Hell, as a woman, I was popular. As a guy, I was no one. Now that was all going to be upset.

"Got a good pic of you kissing that guy as he fondled you. The office should love that."

"He... kissed me, I didn't kiss him. Please don't show that around the office."

"You seemed to be getting into that kiss. And shouldn't everyone have a chance to see the real you?"

"I do this on weekends. When we go out. I don't..."

"Yeah. Sure. Even on the fast dance, you were shaking that ass like nobody's business."

"Please. I'm begging you, don't show that picture around the office."

"What's it worth to you to have us keep your secret?"

"I don't really have much money."

"There's other things you could do."

Susan decided to jump into the conversation at this point.

"Boys, this is not the place to discuss this. Let's go back to our place and we can work this out as friends."

Dave and Mike had come out in one car, and Susan and I in another. Since Dave and Mike didn't know where we lived, I rode with Dave, giving him directions, while Mike rode with Susan.

"You ain't much as a guy, but you're pretty hot as a girl."

I didn't know what to say. I didn't want to make him mad, but didn't want to encourage him either. As it turned out, he didn't need any encouragement, and neither did Mike. What Dave and Mike wanted for their silence was me to suck them off and let them fuck my ass. Now Susan had me suck off her strap on, and regularly fucked my ass with it, but I'd never done either with a man with a real dick.

Susan told me it was blackmail and extortion, but unless I wanted to be outed at the office, I probably needed to go along with it. I didn't care for it, but realized she was probably right. I didn't want the whole office to know I dressed as a woman -- even if it was only on weekends. She said she'd try to ease into it and see if we could get them to settle for less than they wanted.

"You know, boys, she has real boobs -- small ones, but kind of nice. Would you like to see them and touch them?"

Of course they wanted to. Susan pulled my top off and unhooked my bra, to let my boobs out.

"Damn, girl. You been hiding shit from us."

Dave started playing with one boob as Mike played with the other one. Having these guys touch me kind of disturbed me, but as they played with them and sucked on them, it began to feel pretty damned good. At one point, I had one mouth on each boob, sucking, licking, and kissing them like they'd never seen boobs before. I had waves of pleasure ripping through my body as they enjoyed my boobs.

"That was nice for the prelims, but let's get down to business."

Dave stood up, unzipped his pants, and pulled out his prick. I looked at him, and his face was consumed with lust. Mike was nearby and touching his groin. Susan grimaced, but nodded. I edged forward and took the head of his dick in my mouth. Dave moaned.

"God, baby. Do it. Suck that dick."

I could taste a little of his precum on his dick, as I slowly took the shaft into my mouth until I almost gagged. I closed my eyes and pretended it was Susan with her strap-on. At least I tried to. The feel was different, the taste was different, and Dave moaned as I pistoned his dick in and out of my mouth. To keep from choking on it, I put my hand around the base of his dick and rubbed it as I worked on the rest of it.

Dave's groans and moans became louder and more frequent until he grabbed my head and pulled it to him. I almost choked as his dick went down my throat, particularly when he came in a great gush right into my throat.

"Swallow it, bitch."

I didn't really have much choice. Half of it was down my throat before I could have done anything else. Dave smiled and stroked my head.

"You're a good little dick sucker, girl."

Mike was next, and it went pretty much the same. I hoped after sucking them off that they'd be happy and let it go. But both of them insisted on fucking my ass as well. Dave had recovered first and unzipped my skirt and pulled it off. He took my panties off, but my gaff covered my asshole, so he pulled that off too. My tiny dick popped loose.

"Not much there, but it isn't going to get any use from us anyhow. Cute little plug there, girl."

Dave tugged at my butt plug and I tried to relax the muscles as he eased it out of my ass.

"Look boys. You have to use lube. I'm not going to let you ruin her or hurt her. And gently, boys, gently."

Susan produced the lube and Dave smeared it on his dick and around my asshole. I got down on my hands and knees, like I do for Susan, when she fucks my ass. Dave came up behind me and grabbed my hips. I could feel the head of his dick against my asshole as he eased forward. It was already stretched a bit from pulling out the plug, and he slid in pretty easily. Susan had been fucking my ass, but the flesh and blood dick felt different. He pressed in until I could feel his balls slap my ass.

"Damn. Nice to go real deep. Better than I could get with her mouth."

Dave started slow, building up speed, shoving his dick deep into my ass with each stroke, holding my hips tight to guide it. He went faster and faster and I almost forgot it was a guy fucking my ass, until with a groan, he pulled my hips tight against him with his dick as far in me as he could get it. I felt it throbbing and knew he had just cum in my ass. As he came, so did I, squirting my cum onto the bed as he shot his in my ass.

"Isn't that cute. The little girl came at the same time."