Rich has an Adventure

"Well, sis, don't do anything I wouldn't do."

"Is there anything you wouldn't do?"

"Not as long as it feels good and doesn't leave any scars."

Sarah and I went to her room. We worked on math for a while. I'd rather have done some other things, but Sarah wanted the math help first. Once she was satisfied, then we undressed and made love. As much as I hated dressing up for her, I loved what it got me. I guessed as long as she was willing to make love to me, I wouldn't complain about how I had to dress.

Afterwards, I dressed, and Sarah decided to shower before dinner. She kissed me goodbye and I went downstairs to leave. As I did, Suzanne was there, and stopped me. She looked me over very carefully.

"I know that I know you from somewhere."

"I can't imagine where."

All of a sudden, she looked much closer at my face, had a shocked look, her eyes got very wide, and Suzanne had the biggest grin I've seen in a while. My blood ran cold, even before she said another word.

"You're that one nerdy guy I went to high school with. What was it, Rick, Ricky, Rich, something like that?"

"You... you must be mistaken."

"No. I'm damned good with faces." She paused and looked me over again. "I never knew you were into dressing in drag."

"I'm not. I did this first because Kelly wanted me to, and now because Sarah wants me to."

"I'd stick to that story, if I were you. Well, get out of here, girl."

I left quickly and went back to Kelly's house and changed back to my boy clothes and cleaned off my makeup. Shit, here I was trying to keep this a secret, even if it did get me into bed with Sarah, now Kelly, Sarah, my mother, and Suzanne all know. How can I ever keep this a secret?

...

The next day, as I was getting ready to go to school, my mother asked me to drop something off for my father on the way. She had to go to work in the other direction and was already running late. I got to the auto repair shop that my father managed, and walked in. Who was there, talking to my dad, but Ben. I acted as though I didn't know him, hoping he wouldn't recognize me without makeup and girl's clothes.

I had to wait until they were done discussing the repair Ben was working on. As they finished, Ben looked at me, then smiled. My father turned and introduced me as his son.

"Actually, we met the other night at a party. I have to say, your son looks pretty good in a skirt."

"What? What are you talking about?"

"She was there in full drag. She spent time with my ex-girlfriend and me. Even danced with me and kissed me."

"Is that true, son?"

I couldn't speak. Tears formed in my eyes. I handed my dad what my mother wanted me to give him. I turned and ran out of the place. I could hear Ben laughing as I ran out.

"Hey, Rachel, maybe you and I can get it on again sometime soon."

I was a mess as I went to school and did my classes for the day. I got a text from Sarah, asking for Rachel to come to her place later. I texted back, telling her about what Ben did. She texted asking to meet me between classes.

"Ben was kind of a shit the last time I talked to him. He said he wanted to get back together, and I told him I didn't want that and that I was seeing you."

"So that was his revenge on me?"

"Probably, and that means that I will never get back with him, regardless of whether you and I stay together."

"Your sister recognized me last night when I was leaving."

"She told me. She seemed to think it was funny that I was fucking a guy who dressed as a woman. I told her that you were lots better in bed than Ben ever was."

"So can I come over there dressed normally?"

"You're a lot cuter dressed as a woman."

"I don't know if my nerves can take this. And my dad - he's probably already gone ballistic."

"You haven't talked to him?"

"And I'm afraid to."

"Come by my house later as Rachel. Please?"

"Okay."

It was pretty much a repeat of yesterday, except instead of Suzanne puzzling about who I was, she smirked as she let me in the house. As I was about to go upstairs to Sarah's room, Suzanne grabbed my arm.

"My little sister seems quite taken with your oral skills. If you weren't such a nerd and such a fairy, I might be tempted to find out for myself."

"If Sarah didn't insist on me dressing like this, I'd just look like a guy."

"You're a lot cuter as a girl than you ever were as a boy. But I still prefer boys who look like boys and girls who look like girls."

"I'd prefer to look like a boy."

"Right." She said with a real sarcastic edge to her voice.

Suzanne let me go and I went to Sarah's room. More math tutoring before having some fun. We talked a bit after fucking.

"Do I have to keep dressing this way to be with you?"

"My parents are coming home tomorrow. They won't let me bring a boy to my room and lock the door, but they will let me bring Rachel."

"How did you and Ben...?"

"We snuck off. It was kind of exciting, not knowing if we might get caught, but this is a lot more fun and comfortable, and exciting in its own way."

"I'm worried about my dad, though."

"I stopped and told him you're my boyfriend, and Ben was being jealous."

"I hope that's enough."

I went back to Kelly's to change and clean up before putting my own clothes on and going home. I did stay there doing school work for as long as I thought I could get away with. Finally, I broke down and went home.

My father was sitting there when I got home, still glowering. He motioned for me to sit down. I did and my mother joined almost immediately.

"Your little girlfriend came by the shop this afternoon."

"She said she did."

"She told me you had lost a bet with Kelly and had to come to her sister's party dressed as a girl to satisfy the bet."

"I know I shouldn't have done that, but, I got to know Sarah and when she broke up with Ben, she wanted to see me."

"There's more to it than that though, isn't there?"

"What do you mean?"

"I saw you go to the Lopez house today, dressed as a girl."

"That's - that's so her parents won't object to her being alone in her room with a guy."

"I don't like it - not at all. I never thought I'd have a son who was some kind of fairy."

"If I were a fairy, would I been seeing and making love to a girl?"

"Don't ever come home dressed that way - not ever. You understand?"

"I promise, I won't."

"It's humiliating enough, just having a son who dresses like a fairy."

I went to my room, shaking as I went. I'd been half afraid he'd throw me out of the house. He didn't do that, but it was still kind of scary. My phone beeped with a message shortly after I got to my room. It was a text from Kelly. She said she was going to be back in town this coming weekend, and she was looking forward to us girls going out and having fun together.

I texted back that I was spending a lot of time with Sarah, not mentioning how Sarah wanted me to dress. Kelly texted back that she, Suzanne, Sarah, and Rachel could have a great girl's weekend. As I lay there on the bed, the door opened, and my 18 year old sister Julie came in the room.

"Hey there, big brother, or should I say, big sister?"

"Shit, you too?"

"You were too taken with Kelly and Sarah at the mall the other day to notice me, weren't you?"

"You saw me in the mall?"

"You're kind of cute as a girl."

"Is there anyone in town who doesn't know?"

"There are some, but if you keep dressing up that way, eventually lots of folks will catch on."

"I'm only doing this for Kelly and Sarah."

"Keep telling yourself that. Well, it's time for dinner anyhow, sis. Mom asked me to get you."

"Keep calling me 'sis' and..."

"What? You'll cry, maybe?"

"Fuck you."

"No chance of you doing that, besides I thought your little girlfriends had that taken care of."

"Kelly cuddles with me, but nothing more."

"Except get you to dress up for her."

"Not that I want to."

"Then why do you...? I know, you've been checking their house. You put on some of her clothes and she caught you, didn't she?"

"Why do you think that?"

"And I heard about the party from a friend. They told me some girl went off with both Sarah and Ben."

"That doesn't mean..."

"Now you're seeing Sarah. And you did both of them didn't you? Both Sarah and Ben."

"You think I would...?"

"I know Ben would, and from what dad said, it sounded like Ben said you did."

"I'm not interested in guys."

"But you let Ben fuck you for a chance to fuck Sarah."

"Julie, please."

"Just understand, if you want me to keep quiet, you and I will have a sisters' day at the mall."

"Kelly is going to be in town this weekend and she said that we would..."

"So we'll just have one more girl in the mix - you, Kelly, Sarah, me, and maybe even Suzanne, if she's in the mood."

"I don't know..."

"You have Sarah to spread her legs for you, the rest of us just to hang out for a girls' outing."

"Why do all of you want this?"

"Why not, sis? And you didn't get all the nail polish off, by the way."

I looked and saw that I'd missed the little finger on my left hand.

"Cute color for you, and you have a few traces of lipstick in the corners of your mouth."

"Shit."

"Too bad you have to take all that off when you come home. Do you leave the clothes at Kelly's place?"

"They were her clothes, now she says they're mine."

"What are you going to do when her parents come back?"

"She told me to bring them back here."

"Dad should love that."

"I don't..."

"Let's go get dinner. Tomorrow you're going to dress up for me too - you just won't get the kind of payoff you get from Sarah."

"Shit. Am I ever going to get to be a normal guy again?"

"And lose Sarah, and miss all this fun?"

"Sarah, I like, the fun I could do without."

"Come on, sis, let's eat."

"Don't call me 'sis'."

...

The next day, after work and school, I changed at Kelly's and was driving over to see Sarah. I heard a sound and looked in the mirror and saw flashing lights from a police car. I'd been trying to drive carefully because I didn't want to get pulled over. I pulled into a parking lot and the officer pulled in behind me. I rolled down my window and waited nervously as the officer walked to my car door.

"Do you know why I pulled you over, miss?"

"No, officer."

"You failed to come to a complete stop at the last stop sign. It was a rolling stop, never a full and complete one."

"I'm very sorry officer. I'll be more careful from now on."

"I need to see your license and registration."

That was what I was afraid of. I had a purse and pulled my wallet out of it and got out my driver's license and car registration and handed it to the policeman. He took them from me, then glanced at the license, looked a bit startled, then looked at me again.

"You are Richard Wilson?"

"Yes, officer."

"Please get out of the car."

I opened the door and slowly and carefully got out of the car. I stood up and could feel my knees shaking as I stood there. He looked again at the license and at me.

"Right age, right height. But why is a male named Richard in a skirt, blouse, and makeup?"

"It's kind of hard to explain."

"I'm waiting."

"My girlfriend is a little kinky and asked me to come see her dressed like this."

"Your girlfriend? And would this girlfriend have a license saying she is male or female?"

"Female - and she's got all female parts."

"Like born with them, female?"

"Completely."

"Shit. Why do I always get the weirdos and queers?"

"I'm sorry, officer."

"All right, Richard, or whatever you call yourself, if you want to stay out of trouble, either dress right for your sex, or follow the traffic laws to the letter. Understand?"

"I was trying."

"I could run you in, and believe me, you'd be a real hit in the holding cell."

"Please don't do that."

"I'm going to give you a warning and let you go because I don't need the grief, but the next person who stops you may not be as nice."

"Thank you, officer."

"Now get your ass in the car and get out of here."

I was still shaking as I got back in the car. I drove very carefully through the parking lot until I was well away from the police officer, then got back on the highway, still shaking. I was still pale and shaking when I got to Sarah's place.

"What's the matter, Rachel?"

I told her about the traffic stop and we went to her room and we spent a long time with Sarah just holding me and stroking my head until I calmed down a bit. As it turned out, Sarah was pretty happy. She had taken a math test, and instead of the D- that she'd gotten on the last one, she got a B- on this one. We cuddled for a bit before working more on her math, then making love again. As I left, I saw Sarah's mother.

"You must be Sarah's friend, Rachel."

"I am."

"You've been such a great help in getting Sarah on track with math."

"I'm good at math, and it's my pleasure to help her."

"Well, darling, you're welcome here anytime."

She hugged me, and kissed me on the cheek before I left. I guessed I'd have no problem visiting Sarah, at least as long as I was Rachel. I drove very, very carefully back to Kelly's house. I no sooner got there, than there was a knock at the door. It was Julie, who had been watching and saw me drive up.

"Hey, sis. I wanted to get an up close look at your transformation."

"Fine, Julie, take a look and let me change. I need to do some schoolwork."

"Do your schoolwork dressed like that. I like the new look."

"I need to change."

"You can do your work dressed just like that, now sit that cute little ass down. I've got my own homework to do too."

Why the hell do all the women my age want to see me dressed as a girl? I'm not sure, and not sure how I'll get out of this. Well, Julie might be making me stay dressed up, but she wasn't giving me the kind of grief that I often seemed to get from her. We each finished out work and she wanted to sit cuddling with me for a while before we went home.

"I always wished I had a sister, and I guess now I've got that."

"A reluctant sister."

Julie had me show her the outfits that Kelly set aside for me. There were three tops, three skirts, and a few changes of bras and panties.

"Rachel, you and I need to go to the mall."

"Okay, just give a few minutes to change."

"No dice. You need a couple more outfits as Rachel. You're going like this."

At her insistence, we went to the mall, though I made her drive. After my traffic stop earlier, I wanted to avoid driving as much as I could when I was Rachel. She took me to Victoria's Secret, and had me get more panties and bras. Then we went to another store where she picked out a couple of skirts and tops for me. I had to go in the women's dressing rooms to try them on, which embarrassed me a little.

Julie called our mother and told her we were at the mall and going to grab a bite to eat there. We hit the food court for some Chinese, when I realized I needed to pee.

"Okay, Rachel. Let's go to the ladies room."

"Can't we...?"

Julie took my arm and marched me to the women's restroom and steered me into a stall, after telling me quietly that I'd need to sit down to pee. Perhaps, oddly, no one seemed to pay any attention to me in the restroom. I just peed, washed my hands and we left.

"It's too bad we can't keep you dressed this way all the time."

"Hell, no. First dad would kill me, and second, I'm not going to school or work dressed like this."

"That's a shame. We'll just have to work on that."

We went back to Kelly's for me to change. Julie insisted I keep wearing panties and not take off the toenail polish. At least I got to change back into jeans and a tee, and shed the bra and the makeup. Julie and I went home, but she insisted on carrying our purchases with us.

"When Kelly's parents come home, you'll have to have your girl clothes at home anyhow."

"Assuming I keep wearing them."

"You will. Between me, Kelly, and Sarah, we'll make sure of that."

So now I'm trapped into cross dressing until the women I know decide to let me out. The question being, how long would it take for them all to get tired of this.