Rich has an Adventure

"Do you go out dressed this way very often?"

"I've never done it before."

"Why did you start tonight?"

"Kelly made me, after she caught me."

"So how do you like partying as a girl?"

"I'd much rather be partying as a guy."

"Do you think any girls would be paying any attention to you if you were?"

"Probably not. Certainly no one as pretty as you."

"You think I'm pretty?"

"You're very pretty."

"As pretty as my sister?"

"I'd take you over her any day. You're so much sweeter and nicer, that it doesn't matter which of you is prettier."

"Do you like girls?"

"Yes, and I really like you."

"What about guys?"

"I'd rather not."

"What if I said that you and I might have some fun, as long as Ben could join in, too."

"What would he do?"

"He'd probably do both of us. Ben swings both ways."

"I don't know."

"Think about it. It's still early."

About that time, Ben returned with the drinks. Sarah gave me a very passionate kiss, then gave one to Ben as well. Ben turned, grabbed me, and gave me a kiss also. What scared me was that while I really liked Sarah's kiss, I liked Ben's kiss too. Honestly it scared me a bit, even as it turned me on.

We continued to talk, dance, and drink, and the punch started to get to me and I felt light headed. Being under 21, I had never done much drinking and didn't even know how to gauge it all. Along with the drinking, Sarah and I continued to make out, as she made out with Ben as well. Ben didn't seem to leave me out and I found myself making out with him too. I was befuddled, as well as being drunk.

"Rachel, Ben, let's go some place a bit quieter."

I was in no shape to argue, and figured she meant we'd go outside, away from the music and most of the people. Instead we went to Sarah's bedroom. Sarah pulled me down on her in bed and we kissed for a few minutes, before she wanted something more.

"Rachel, baby, would you go down on me. Ben doesn't care much for that."

She gently pushed me down her body, then as I got down far enough she pulled up her skirt and lifted her hips off the bed. I pulled her panties down and she dropped her hips, spreading her legs and lifting her feet so I could pull them all the way off. I looked to see her pussy right out there in front of me. I'd never seen one live and in person and reached out to stroke it gently.

Sarah wasn't shaved, but had her bush trimmed short, with a soft covering of fur. She lifted up, grabbed my head, and pulled it into her sweetness. I wasn't quite sure what to do. I kissed her pussy, then she told me to stick my tongue in it. Before long she had me licking it and sticking my tongue and fingers as far into it as I could and I even managed with her help to find her clit.

Sarah really seemed to be getting into what I was doing and the longer I went at it, the fewer instructions she seemed to have to give me. She began to moan and wrapped her legs around my head and pulled me in close. Between my own activity and the alcohol, I barely even noticed that Ben pulled my skirt up over my ass.

I felt him pull my panties down, and wondered what he was up to, but Sarah held me tight with her legs and she began humping my face. As she did, Ben began to ease his cock in my ass. At first, I really didn't like it. It hurt some and the thought of a guy fucking my ass was kind of a turn off. Sarah was not turning me loose and there was little that I could do.

He was pretty gentle, first easing the head just inside my ass, then pumping and getting deeper on every stroke until I felt his hips up against my ass. As much as I hated the thought of it, as he continued, it felt good in there. Meanwhile Sarah was squirming and writhing under my tongue and mouth and I could feel my face wet from her juices.

Sarah was holding my head in her hands, besides having her legs wrapped around my neck. I loved that and loved licking her pussy. Sarah seemed to like it too, and was pumping her hips as though she was fucking my tongue and face. She got wetter and wetter as she moaned and squirmed. She pulled me tight and I could feel her muscles rippling in her abdomen, even as she squirted me in the face cumming.

As Sarah was getting off on my mouth and tongue, Ben fucked my ass. He started slow and gentle, getting his cock deep in me. As he went along he picked up speed and began to fuck me harder and faster. My mind rebelled against the idea of a guy fucking my ass, but my body loved it. It felt so good, I couldn't help but fuck him back. Shortly, he pulled my hips tight and filled my ass with his cum.

He kept his dick in my ass as it throbbed and pumped what felt like gallons of cum into my bunghole. As he finished emptying his balls into my ass, Ben slowly eased his prick back out of me. He let go of me and I sort of slumped over onto my side. Sarah rolled over and slid down beside me and kissed me as I lay there recovering.

"Well, Rachel, I got off and Ben got off, but you haven't had a chance to get off yet. Let's get you out of some of these clothes."

Sarah pulled off her skirt, top, and bra, letting her cute little boobs bounce free. Ben unzipped my skirt and pulled it off me, having already removed my panties to fuck me. Sarah pulled my top off me and unhooked my bra. Sarah had some definite things in mind.

"Ben, go wash that thing off."

Ben went in the bathroom to wash my shit off his cock. Meanwhile Sarah kissed me a bit before getting on her hands and knees and having me get behind her. She grabbed my cock, which was rock hard from what we'd already done, and eased it into her pussy. So my first time fucking a girl would be doggy style. I had no complaints and got it as far into her as I could before fucking her.

Ben came back and got in front of Sarah who began to suck him off as I fucked her. I loved the feel of her pussy as I drove my dick deep into it. My only regret at that point was that I had wanted to spend more time kissing Sarah and playing with her boobs. Hard to complain when I was with a naked girl who was letting me fuck her.

Her pussy felt so wonderful on my cock, it took all my willpower to keep from cumming in her. Now Sarah had told me that Ben was bisexual, and of course he'd already fucked my ass, but it still surprised me when as Sarah was sucking his dick while I fucked her, that Ben bent forward, pulled me toward him, and kissed me.

I couldn't help but kiss him back, though I was conflicted over kissing a guy, even a guy who had fucked me. He kissed me for a minute or so, before he really started getting into what Sarah was doing to him and he straightened up and grabbed her head to push even deeper into her mouth. He pulled her tight and moaned as he shot his cum down her throat.

As he finished cumming, Ben slumped back onto her bed, as I continued to plow her pussy. Sarah told me to stop, then pulled out, rolled onto her back and pulled me down on top of her, putting my prick back in her pussy. Now I was truly in heaven. I kissed Sarah and touched her boobs as I fucked her. Very quickly after, I came in her.

For a few seconds, my world narrowed to the feel of my dick filling her love canal with my cum. As I returned to this world, I resumed kissing her and playing with her boobs as my dick finished emptying itself into her. A few hours earlier, I was a nerdy guy and a virgin, and now had fucked a cute girl who I'd eaten out just before.

I found we were not done yet, as Ben made me get off Sarah. He got her back on her hands and knees and began to fuck her doggie style, leaning down over her back, then pulled me up behind him and told me to fuck his ass. My dick was still sloppy with Sarah's juices and I came up behind him and fumbled a bit, before he paused in fucking her to guide my cock into his ass.

Honestly, what I really wanted was to be alone with Sarah, fucking her and making her feel good. But Sarah was Ben's girlfriend, and I was the third person who got invited to the little party. They were calling the shots, not me and since I was getting my rocks off, I couldn't exactly complain about it. I guess I was bisexual enough not to be freaked by it all, I'd just rather have been with only Sarah.

Ben's ass was even tighter than Sarah's pussy, though I loved being in Sarah's pussy. Pretty quickly we fell into a rhythm where Ben was doing a lot of the work. As he plunged his cock into Sarah, mine came nearly out of his ass, and on the back stroke, my cock went in his ass as he pulled back from her. I just closed my eyes and thought about Sarah and how it felt fucking.

Say what you will, I was fucking something and it felt good. Maybe if things worked out I'd get some one-on-one time with Sarah. I felt it building up and plunged deep into Ben's ass, as I came. While I was cumming, he came in Sarah. After that session, we all felt good, but tired.

"Rachel, you need to clean up and get dressed and get back to Kelly. And we all need to get back to the party."

I cleaned up a bit and put my panties, skirt and top back on. Sarah and Ben both dressed and we all returned to the party. Sarah and I exchanged numbers so I could help her with her math. I found out from Sarah that Ben mostly liked to do guys in a threesome with a girl, not so much one-on-one.

Back at the party, we found Kelly, who was ready to leave, and wondered where I'd gone. Sarah kissed me, patted me on the ass, and sent me off with Kelly. I needed Kelly, because she still had my boy clothes, and I didn't want to go home dressed like this. There were a couple of guys, who were pretty drunk who said they wished they'd been able to spend more time with me, and insisted on kissing me goodbye. Finally we got away from the party and Kelly drove us back to her house.

"So Rachel, how did you like your experience?"

"It was okay."

"Okay? It got you laid, didn't it?"

"Yeah, but not just Sarah. I fucked her, but Ben fucked me too."

"Damn. When you lose your cherry, you go big time."

"Kind of a package deal. I wasn't going to get Sarah, without letting Ben do me too."

"Was that so bad?"

"It wasn't horrible, but I'm in no hurry to let a guy do me again."

"What about Sarah?"

"If she'd let me, I'd do her again in a nanosecond."

"What if she only wants you if you're dressed like this?"

"Shit. I never thought of that."

"Tell you what, girl. I'll take a few of my clothes and set them aside and you can wear those anytime you want, for whatever you want, as long as you leave the rest of my clothes alone."

"That only helps while your parents are out of town."

"You can take them with you, when they come back."

"I'd have to figure out how to hide them from my parents."

"If you really want Sarah, you'll figure it out."

By that time, we were back at her place. I just wanted to get my regular clothes, change, and go home. Kelly seemed to have some different ideas.

"Come sit with me on the sofa. I won't fuck you, like Sarah did, but we can cuddle a bit."

We sat on the sofa and Kelly put her arm around me and put on a romantic movie on one of the cable channels. She had me rest my head on her shoulder, and stroked my head as we watched the last half hour of the movie. Typically, the couple finds some reason to break up, then get back together in the last five minutes, ending the movie with a kiss. As the credits begin to roll, Kelly gave me a passionate kiss.

"That's it for tonight, Rachel. You need to wash off your makeup, and I'll get your boy clothes for you."

"I wouldn't mind spending more time with you, Kelly."

"I'm not going to be your girl, but if you play it right, you might land little Sarah."

"She's very pretty and very sweet, but I thought she was seeing Ben. I really don't want a lot of threesomes with Ben."

"Even if it means getting Sarah?"

"I don't know."

Kelly got a makeup wipe and cleaned the makeup off my face. She then got nail polish remover and cleaned off my fingernails. She refused to do my toenails.

"I want you to keep that on. Just means you'll have to wear shoes."

I began to take off my girl clothes, but Kelly told me to keep the panties on. "That's just part of the price you pay for wearing my clothes."

I took off the skirt, bra, top, and her shoes, and she gave me back my regular clothes except my jockey shorts. Before she did, she shot one more picture of me standing there in nothing but her panties. She said she'd wash the rest of what I wore that night and showed me where she was going to put the clothes for me.

I dressed, and she told me that she expected me back around lunch the next day, even if she was at home. She said we'd have more fun then, and told me not to take off the toenail polish on my own. Once I was dressed, she gave me a quick kiss and sent me home. It was far later than I normally ever got home, and I found my mother was up.

"I guess you had a good time, Rich."

"Yeah, I guess so."

"So what did you do?"

"I ran into a friend from high school and she invited me to go to a party with her."

"You had a date?"

"Not really a date. I was just her escort."

"You aren't exactly dressed for a party."

"It was kind of a costume thing, and she had a costume for me."

"So are you going to see her again?"

"We aren't really dating, but I met another girl and we talked and I'm going to help her with a class she's taking."

"Your friends are over 18, I hope."

"Absolutely."

"Good, we wouldn't want any of those kinds of problems."

"No, not at all."

"And you may want to get some condoms, just in case things get more intimate."

"Mom! Really."

"You don't want any diseases, and don't want to make any babies."

"I'm not really comfortable..."

"Maybe not, but you still need to think about these things."

"Good night, Mom."

With that, I scurried out of the room and went to my bedroom and closed the door and locked it. I took off my clothes, including the panties I got from Kelly. I could see where some of Ben's cum had leaked out of my ass into the panties. I'd have to figure out how to wash them without my mother knowing. I'd also have to wear shoes outside my bedroom, at least until Kelly went back to school.

I stuffed the panties in the toe on a shoe, in hopes no one but me would find them there. I put on some pajamas and went to bed. I fell asleep pretty quickly and found myself dreaming about being dressed as a girl and fucking both Sarah and Ben.

...

I got up and was about to go down to the kitchen in my pajamas, when I looked down and saw my toenails. I put on some slippers and rushed to the bathroom to shower, taking pants and shoes with me. Usually, I just came out of the bathroom with a towel around me, but not today. I got back to my room and had a text from Kelly. She said she'd see me at noon, and that I should be wearing those panties when I came over.

I snuck back to the bathroom, where I washed the cum out of the panties, and used a hair drier to dry them enough to wear. Now, let's be honest, wearing the panties was a turn-on for me, but I was paranoid about the idea of anyone else knowing that I was wearing them. Once they were dry, I put the panties back on, with my jeans over, and a long tee shirt, tucked into the jeans, so no one could easily tell I was wearing them, even if I bent over.

I was conflicted. What Kelly made me do, got me the first sex of my life, and did turn me on. I hated that she could pull my strings and make me do whatever she wanted. I had the sneaky suspicion that it would only get worse.

I went to the kitchen, and my mother gave me some breakfast, though she seemed surprised that I was dressed already.

"I have to go check on the Jacobson's house a little earlier today. Then I need to do some school work, so I may be gone for a while."

"You have classes tomorrow, so don't be out too late - not like last night."

"I won't, Mom."

I ate my breakfast, rinsed off my dishes and put them in the dishwasher. I gathered my computer and other stuff. I also grabbed a change of clothes and put them in my car, just in case Kelly decided to dress me up again. I went to the library for a little while, then over to Kelly's house, arriving just before noon. Her place is close to mine, but I'd driven to the library, so I drove to her place.

Since I felt sure Kelly was home, I knocked on the door, and Kelly answered. I have my own key and code, but wasn't going to barge in since I knew she was there. Kelly opened the door and waved me in, stopping to give me a kiss on the cheek.

"We're going to have some fun this afternoon."

"We are? Or you are?"

"You didn't have fun at the party last night?

"Yeah, I just..."

"Wouldn't have had near as much fun if you'd looked like this." Kelly gestured at my outfit.

"What do you have in mind?"

"We're going to the mall for lunch and a little shopping."

"You and I?"

"Me and Rachel."

That was what I was afraid of. She was going to dress me up again. I wasn't sure what if anything I could do about it.

"Because you've got the pix of me dressed up in your clothes."

"I also have a couple of shot of you at the party, plus slow dancing with Ben, including one where he's giving you a kiss."

"Shit."

"Really cute pix."

"So I dress up for you again."

"Are you wearing your panties?"

"I am."

"Then let's get started."

Kelly led me to her bedroom, and showed me another outfit from the ones she set aside for me. She had me change into it, then styled my hair and did my makeup, and painted my fingernails again.

"It's a shame we had to take off the polish last night, but I didn't want to out you - certainly not yet."

"What do you mean, not yet?"

"I'm just teasing you. I won't out you as long as you do what I say."

"I don't know how reassuring that is."

"It'll have to do."

Kelly sat me in front of a mirror and explained what she was doing with the makeup as she did it.

"I'll do your makeup now, but you're going to have to learn to do it yourself."

"Why?"

"I called Sarah. She's going to want you to be Rachel at least part of the time when you're with her."

"Fuck."

"If you behave, she might."

I wasn't sure how much I liked that. Sure, I enjoyed being with Sarah. She was the first girl I was ever intimate with - well the only one, actually. I certainly wanted to spend more time with her, and if possible to fuck her again. I wasn't sure I liked the idea of being Rachel in order to get Sarah into bed. I also wasn't sure I wanted another threesome with Ben.

I guess you do what you have to in order to get what you need. At any rate, I paid attention to what Kelly told me about doing makeup. I'd never done it before. I had been quite happy jerking off just wearing her clothes. Sure, I managed to get real sex last night, but at what price. I guess I'd get more, but still only be dressing up as a girl.

Once Kelly had me dressed and made up to her standards, she said we were going to the mall. Mind you it was bad enough going to a party dressed like this last night, but the mall seemed so much worse. But unless I wanted Kelly to post pix of me in drag, I guessed I'd be doing whatever she wanted. So we went to her car and she drove us to the mall.

I was starting to get used to getting in and out of a car in a skirt, without showing the world my panties. I still felt like every eye in the surrounding area was on me as I got in or out of the car, or even as I walked around in a skirt and top. Kelly took me to one department store where we bought some makeup in "my colors" whatever the hell that was supposed to mean.

The clerk redid my makeup and gave me some additional tips on applying it. If I wasn't careful, I might actually learn something about putting makeup on. I guess I needed to know, at least as long as Kelly or Sarah could pull my chain. We went to the food court and got some lunch. Kelly made me get something other than just a burger and fries, and made me eat it more ladylike. We were joined by a couple of guys from my high school class and the year before.