Rich has an Adventure Ch. 02

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This includes cross dressing, incest, straight sex, lesbian sex, male-male sex, group sex, and nonconsensual sex. If any of that bothers you please skip this story. The emphasis of this is story, though there is some sex.

I don’t often do sequels, but it felt like there was more to go to cover Rich’s story.

For those who didn’t read the first part, Kelly caught Rich wearing her clothes and made him go to a party dressed as a woman, calling her Rachel. Rachel met Sarah who fell for her, but Sarah wanted Rich to be Rachel when they were together.


I kind of fell into a routine. Once I was done with school and work, I’d go to Kelly’s house, make sure everything was okay, then change into the clothes she gave me and go see Sarah. We’d spend an hour or so working on math, before making love. I’d go back to Kelly’s place and hang out with Julie, who insisted I stay in those clothes until it was time to go home.

On the weekends, Kelly would often come home and I’d spend much of my weekend in girl time with Kelly, Sarah, and Julie, along with Suzanne occasionally. We had a couple of other girls effectively join the circle, Chloe and Michelle. When we went on girl outings, we seemed to attract a swarm of guys, but word slowly got around that Sarah and I were a thing, so I had fewer guys hitting on me.

One part of me still rebelled against dressing as I did and wearing makeup, but once I was changed and with the other girls, I barely even noticed anymore. Sarah seemed very happy being with me, though she liked to flirt with guys to make me jealous. It went pretty well, until the weather warmed up and Kelly’s parents came back to town.

I couldn’t go change at her house any longer, so I had to figure out something else. I also couldn’t exactly change into my girl clothes at home. To make it easier, faster, and less embarrassing to change, I ended up wearing panties nearly all the time. I’d wear jeans and a tee as a boy, then when it came time to change, I’d find someplace out of the way and change in my car.

I kept the girl clothes in my car and would take off my tee shirt and put on bra and a top. I had upgraded to getting some breast forms to look better than the socks I previously stuffed my bras with. Once I was changed above the waist, I’d slip off my shoes and socks, then put a skirt on over my jeans, then take the jeans off once the skirt was on. After that, I’d hit a bathroom to do my makeup.

I kept toenail polish on all the time, but often did not have my fingernails polished, except when we did a girl outing. When time came to change back, I’d pull my jeans on before taking my skirt off, then quickly taking off my top and bra before putting my tee shirt back on. I’d always clean my makeup off before changing back into my boy clothes.

I had to be careful where I changed, but even then got caught by a police officer one time. I parked my car, cleaned off my makeup and had pulled on my jeans when there was a knock on my car window.

“Excuse me, miss. What’s going on here?”

“I was… well I was just trying to…”

“Please get out of the car.”

I got out of the car, still with my skirt on over my jeans. I was still wearing a bra and a girl top, though I’d kicked off my girl shoes.

“I need to see your license and registration.”

“The car was stopped and turned off.”

“I saw you drive in here, and clearly no one else is in control of that vehicle.”

I gave him my license and registration and he looked at it. He shook his head and groaned.

“Shit, one of those. Can’t you fairies find some place private to do your queer shit?”

“I was just trying to change clothes where I thought no one would see me.”

“You failed. I ought to run your queer ass in.”

“Please, officer. I’m always careful never to expose myself, even when I change.”

“What really sucks is that you’re better looking than my girlfriend.”

“Don’t arrest me. Please.”

“What’s it worth to you for me not to run you in?”

“What do you mean? What do you want?”

“Nothing that you don’t do all the time anyhow.”

“What do you mean? What are you talking about?”

“On your knees, girl.”

I got down on my knees, and the officer stepped over to stand immediately in front of me.

“Unzip it, faggot.”

“You mean…?”

“Unless you’d rather go to county lockup. They’d love you there.”

“Please don’t.”

“Then get at it.”

I unzipped his pants. It was obvious that his dick was hard. It was straining at his pants and boxer briefs.

“Take it out, girl.”

I freed his cock from his briefs, and it stood straight out, twitching with a drop of precum already at the tip. I looked up at him, not really wanting to do this, but fearful.

“Suck it.”

I was horrified. Okay, when Sarah, Ben, and I were together, Ben fucked me, but I didn’t suck his dick, Sarah did. And yeah, I’ve had to kiss more than a few guys in my girl excursions, but Kurtköy Esmer Escort again, I sucked no dicks. Now, I had this cop, who expected me to suck his cock in order to have him not arrest me. I sure didn’t want to be arrested – not while wearing a bra, panties, and a girl top, even if I took off the skirt.

I didn’t think I had much choice in the matter though. I leaned forward and took the head of his prick in between my lips. I closed my lips on the head of his dick, and the cop thrust his hips forward, getting more of his dick in my mouth. I began pistoning his cock in my mouth, as far as was comfortable, though he seemed to want it deeper.

“Take it all, bitch. Suck it good. And no teeth – understand?”

I took it so deep it was starting to gag me and kept up a steady pace of fucking his dick with my mouth. He groaned and put his hands on my head, keeping me from getting too far away, and trying to push it even deeper. I took a hand and tried stroking the part I couldn’t easily get in, which seemed to help slightly.

He started really pumping his hips, fucking my mouth for all it was worth. Keeping my hand on his cock kept him from getting too deep in my mouth, but it was still farther than I liked. After a few minutes, he grabbed my head with both hands and jammed his prick so far back I couldn’t even breathe, and then he began to cum with what felt like oceans of cum.

I thought I was going to suffocate, when he loosened his hold, letting me swallow his cum and catch a breath. Finally, he let go of me and I let his cock slip out of my mouth. I swallowed a couple more times to get all his cum down, as he tucked his dick back in his pants and zipped back up. I didn’t like what happened, but even so, I seemed to be turned on – my dick was rock hard after sucking him off.

“Thanks, little girl. Now get in your car and get the hell out of here.”

I got in the car and drove off and tried to find another spot where I could change in peace. I took off my skirt, since I already had jeans on, then took off top and bra and put on a tee shirt. I kicked off my flats and put on socks and shoes, still shaking from the whole experience. At the same time, I was still rock hard, thinking about what had happened.

If I hated it so much, why did I seem to be turned on by it? It just didn’t make any sense to me. I went home and after stashing my girl clothes neatly in the trunk of the car, and went straight to my room. After a little while, Julie came in.

“Hey, sis, how’s it going?”

“Can it, Julie. I’m not in the mood.”

“What’s the matter, girl?”

I told her about the cop, and what he’d made me do. She sat down on the bed beside me, stroked my head, and pulled me tight in a hug.

“That sexist, homophobic asshole. Did you get his name?”

I had been so scared, that it never even occurred to me to look at his name tag. Hell, I didn’t even want to look at his face. I sure knew his dick pretty well though – not that I was going to identify him that way. Julie sat, stroking my head for a long time, before kissing my cheek.

“Look, sis. I know you’re trying to be careful, but you need to be even more careful. That asshole will probably be looking for you to repeat that, if he gets the chance.”

Julie told me about one girl’s bathroom on one section of campus that seemed to get very little use. I know campus was miles away from Sarah’s place and not at all on my way home, but it seemed worth it to go there to change each way, both before and after seeing Sarah.

Things seemed to settle down after that. I had no problems changing in that restroom and no more run-ins with the police. Kelly came home regularly on weekends, and I’d spend a lot of each weekend as one of the girls. I made sure someone else drove when I went out with Kelly, Sarah, and Julie, along with whoever else joined in.

I was sitting in my room, doing school work one evening, when my father walked in, angry, as he often seemed to be anymore, and holding some of my girl clothes.

“What the fuck were these doing in your car?”

“What…? How…?”

“I needed the tool kit in the trunk of your car, and found these there. Would you care to explain them.”

“I wear them to make my girlfriend happy. I never wear them here or around you.”

“That’s bullshit. You wear this shit because you want to. Otherwise you’d find a girlfriend who likes you as a boy.”

“Sarah is the first girl who would ever even give me the time of day, much less go out with me.”

“Make all the excuses you want. You dress like a fairy because you are one.”

“I’m sorry you feel that way. I do my damnedest not to dress that way any time I’m around you.”

“Don’t start with that. You’re a fairy and we both know it. That’s why you sucked off Officer Harris to get out of a ticket.”

“He… he said he was going to arrest me if I didn’t.”

“Not the way he tells it.”

“I’d never done with before with a guy.”

“And Kurtköy Eve Gelen Escort I suppose you didn’t let Ben fuck you.”

“I… It doesn’t matter what I say. You’re not going to believe me anyhow.”

“It’s just too damned obvious what you are and what you’ve done. You make me sick.”

“Then maybe I should just change clothes here, instead of trying to hide it and taking a chance of getting caught.”

“I’m surprised you aren’t wearing your fag rags now.”

With that, he dropped the clothes on the floor, turned around and left the room, slamming the door as he left. I was shaking. I’d done everything I could do not to upset my father, and he seemed totally pissed off anyhow. I couldn’t seem to win. Oddly enough, any more, I seemed happiest when I was in girl clothes with Sarah or the other girls.

If my dad was going to be pissed anyhow, then I decided I’d do all my changing at home. I still went to classes and my part time job on campus in boy clothes, then started to come home to change to girl clothes before going to see Sarah, or on the weekends before going out with the girls. Then when I came home, I didn’t automatically change back, though I did wear boy clothes at dinner.

It was such a pain putting on nail polish on my fingernails and then taking it off that I seldom used it during the week, then I decided to try a muted light pink nail polish. It didn’t scream or slap people in the face but still let me have polish on my fingernails. Sarah loved it and we had an especially passionate love making after I wore it to her house.

My part time job was at the book store on campus. It was good and they’d adjust my working hours around classes and it gave me a discount on all the merchandise. Besides, to keep expenses down, I bought used textbooks and I got first choice to get the best looking ones for my classes. They had all manner of things that students might want to buy including a limited selection of makeup, so I bought stuff there to get the discount.

I thought my new nail polish and makeup purchases were discreet and went unnoticed, at least until the woman who was my supervisor stopped to talk with me one day.

“I love the nails. They’re cute without being flashy.”

“Well, uh… thank you.”

“You buy makeup but don’t wear it to work?”

“I didn’t think…”

“College policies are pretty liberal. If you want to use makeup or dress the way you identify, there wouldn’t be a problem.”

“I… my classes…”

“Most of the professors here don’t care, as long as you show up in class and do your work.”

“And if I wore a skirt to class?”

“Nine out of ten instructors would never turn a hair.”

I decided to talk to my instructors, using the old ‘asking for a friend’ thing. I wanted to know if they would object to a boy wearing a skirt to class. They all said that essentially as long as there was no indecent exposure, they didn’t care what students wore to class. I mean, look, it’s not like I wanted to dress in skirts all the time, but I was spending a lot of effort to change before seeing Sarah.

At that point, my mother didn’t seem to care at all. My sister seemed to like seeing me in skirts, as did Sarah, and my dad simply had constant silent rage, regardless how I dressed. I decided to give it a try for one day, to see what happened. I wore full female attire, including a bra and breast forms, and kept my makeup muted.

I had a few guys look at me funny. I thought I heard a few nasty comments, but the people who said them kept their voices low, so it was hard to tell. Most of the women I went to school with seemed to have no problem with my attire at all. My real conflict was the first time I had to use the restroom while on campus. I stood, with probably a pained expression for a minute. One woman saw me and asked what the problem was. I told her I had to pee.

“Women’s restroom is right here. That’s what it’s for.” She gestured toward the restroom door.

I was a little shaky as I opened the door and walked in the restroom. There were a few women in there, but none of them seemed to pay me any mind. I’d gotten used to using women’s restrooms at the mall, when I was out with the girls, but we always went as a group, so there were friendly faces with me. I just seemed to be one of the girls that day, as well, so I went in a stall and did my thing.

There were no incidents at all that day, and I could go directly to Sarah’s house, without having to stop, change, and put on makeup before going. It seemed to solve problems instead of creating any. At the bookstore, no one seemed to care how I looked, though the woman who was my supervisor, smiled at me, and patted my ass as I went by.

I suppose it should have bothered me that someone patted my ass, even if it was a woman, but under the circumstances, I didn’t want to make any waves. I decided that unless I caught some real flack, I might just as well try to dress this way every day. It was weird. A few months Kurtköy Evi Olan Escort earlier, I’d have been totally humiliated by this, now it just seemed natural.

When I thought about it, it bothered me that I was so comfortable with this. So I just decided not to think about it. I just ended up being Rachel most of the time now. I had no problems with worrying about a cop catching me changing clothes in public, nor with going into a women’s room dressed as a guy to change to my girl clothes.

Sarah looked like she was likely to make a B or C in her math class now and she and her parents seemed ecstatic about that. I mostly saw Sarah’s mother when I came over to her house, along with her sister Suzanne, of course. I got a definite impression that her mom knew that there was something physical going on between Sarah and I, though she seemed cool with it.

Sarah’s mom indicated that she would not approve a sleep-over, not that we ever thought that was a consideration anyhow. Her mom was gone a lot while I was there, so we had a fair amount of freedom to enjoy sex without disturbance or open disapproval. Her dad worked long hours and I almost never saw him during the week, only when we went by Sarah’s on weekends.

I met Sarah’s dad, Andrew, a few times when visiting Sarah. He was quite appreciative of how I’d helped Sarah with math. He talked to me and I told him about my major and some of the courses I was taking. He asked if I was being paid to tutor Sarah in math, and I told him I wasn’t. He seemed to want to pay me and I quietly declined. I was getting Sarah as my lover and seemed payment enough, though I didn’t want to tell him that.

The spring semester was coming to an end, and I started thinking about finding a full time job over the summer, until classes started again in the fall. Mr. Lopez, Andrew, said that his company was hiring summer interns, for full time work paying twice minimum wage. He asked me if I had any interest, and of course, I accepted.

Sure I could try flipping burgers or bagging groceries, but would make less money and have shifting schedules, even if I could get something full time. He was expecting to hire Rachel, because that’s who I was as far as he knew. Then again, I seemed to be Rachel most of the day every day anyhow, so what difference would it make.

I realized that would be a problem in terms of using that company as an employment reference, when I tried to get hired as Rich, but that was at least a year away anyhow, and it gave me the chance to make some decent money now. As I said, my parents were not wealthy, so making double minimum wage for the summer instead of minimum made a big difference in how much money I had for school.

As I thought about it all, I was a little disturbed. Here I was dressing as Rachel pretty much all day, every day. Is that how I wanted to spend my life? Doing that got me the affection of Sarah, and that had become important to me. Did I really want someone who would mold me into someone else? Was I really Rich or was I Rachel? I was beginning to wonder.

As it went, I finished the school year, helping Sarah with math, and making love to her. It was pretty much the same, with some variations. I played with her boobs, which I enjoyed. I went down on her which she really enjoyed and I was pleased to do. We fucked, sometimes with her on top, sometimes with me on top, sometimes doggie style, and sometimes with other positions.

Now Sarah did introduce a few things to it all. She decided that since I was also a girl, I should also be fucked. She got a strap-on and at least a couple times a week, fucked my ass with the strap-on. Honestly, I did it to make her happy. I felt no real desire to be fucked in the ass, even if I had let Ben do that the first time I got with Sarah.

On weekends, Kelly often came to town, but not always. We would do a movie, or dinner out, maybe just wandering the mall, always with Sarah, Julie, and I, and when they were available, Kelly, Suzanne, Chloe, Michelle, and others would join as well. I had become one of the girls. I hung out with them, I dressed like them. We’d get manicures and pedicures together. We’d shop for clothes.

I didn’t have the money of some of the girls, like Kelly, Sarah, or Suzanne, but still after a while had a decent wardrobe of girl clothes. Once in a while, I’d look in my closet, think about how my father felt, think about how often I got hit up on by guys, and wonder if I was on the right track. I’m not sure it mattered. That’s the track I was on regardless.

I largely managed to avoid problems with the police now. I was super scrupulous in obeying the traffic laws. I never even changed lanes without signaling the change. I always stayed at or under the speed limits, and obviously I no longer changed in public or anywhere that a cop could see or anyone could complain. I ran into Ben a few times. Inevitable, I suppose, but I hated ever seeing him.

Ben hit up on me even worse than any other guy. If other people were around, he felt compelled to mention that I was a boy dressed as a girl, and that he had fucked my ass. He kept asking me to hook up with him, talking about how he’d like to fuck me again. Needless to say, I avoided my father’s workplace, where Ben worked, and where I could be certain of my dad’s disapproval.

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