Rich has an Adventure

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jackie_em
jackie_em
1,558 Followers

"Well, well. If it isn't a pair of lovely ladies in need of some company."

No, we were not in need of any company, and I for one sure as hell didn't want the company of any guys. One of the guys named Mitch, had dated Kelly at one time and still had the hots for her. The other guy zoned in on me. He was so cheesy, it was almost funny.

"You must be a magician, because when I look at you, everyone else disappears."

"What would it take to make you disappear?"

"Just give me your number and a date."

"Somehow I don't think my boyfriend would like that."

I wasn't sure where I even came up with that, but was hoping it would discourage him. He was persistent though, and insisted I put my phone number in his phone. He handed me the phone and I entered the phone number for 'dial-a-prayer' and a name of Griselda. He saw the name and did a double take.

"That's the first name my parents gave me."

Kelly heard this and it was all she could do to keep from laughing out loud. I told the guy I was only in town for a very short time and would not be available for a date while I was here.

"So when are you going to be back?"

"I'm not sure, it depends on when Kelly is coming back, and if I'm available then."

"Well, if I can't get a date, I should at least get a kiss."

"I don't kiss strange boys, and you're pretty strange, all right."

"Damn, cut a guy a little bit of slack."

At that point, Kelly piped up. "Kyle, my friend Rachel is not in a good mood, this weekend. I was trying to cheer her up."

"Not very successfully, I guess."

"I know she isn't in the mood for company, but if Rachel gives you a kiss, will you be okay and let her pout by herself?"

"If it's a nice kiss."

"Rachel, honey, please give Kyle here a kiss."

I guess it wasn't as bad as fucking him, but I really didn't want to kiss this guy. Then again, I'd had to kiss Ben a couple of times last night, and at least a kiss would do it. I agreed and Kyle pulled me close and gave me a long passionate kiss. What was really terrible was that kissing him started to give me a hard-on. He was holding me tight, but I tried to keep from having it be apparent.

Kyle also had a hard-on and I could feel it pressing up against me. He even seemed to be trying to rub it against me. When he broke for a breath, I pulled back and told him he'd gotten his kiss, and that was it. He looked disappointed but turned me loose, though he rubbed my ass as I turned away. That made me step away from him that much faster.

Mitch and Kyle left though Kyle patted me on the ass once more before I got away from him altogether. Kelly broke up once they were out of sight.

"That was so funny, seeing you try to discourage him."

"Kissing him and having his hands on my ass wasn't that funny to me."

"Maybe that will teach you something about dealing with women."

"I've never treated women that way."

"Then you're better than a lot of guys."

We continued to hang out in the mall and found more than a few other guys trying to chat us up. Some were friends of Kelly and others just saw a couple of cute girls and wanted to 'know us better'. One guy named Todd seemed particularly taken with me. I sidestepped anything with him, and after he and his friend left, Kelly turned to me.

"For what it's worth, Todd swings both ways, so he probably wouldn't have any problem with what you are."

"Kelly, I'm not looking for a boyfriend. I like girls."

"But you still seemed open to things with Sarah and Ben."

"Not because I wanted to be with Ben. They were my protectors and that ended up being part of the price of having some fun with Sarah."

"And it wasn't that bad, was it?"

"Are you into girls?"

"I've been with girls. Not my first choice, but I enjoyed it."

"I want to be with Sarah, but would much rather skip Ben or any other guy."

"And if it's a package deal?"

"I don't know."

"Well, look who's coming."

I turned around to see Sarah walking up to us. I smiled and she smiled at me. She first hugged Kelly then hugged me and gave me a long kiss with lots of tongue. I really enjoyed it, but far too soon she broke the kiss and let go of me.

"Nice to see you out and about again, Rachel."

"Well, Rachel isn't really out yet, so to speak."

"And I'm not going to be out - not that way."

"Obviously, Sarah, our friend Rachel is a little sensitive."

"We don't want her to be too uncomfortable."

With that, Sarah turned and kissed me - just a quick kiss, but hey, anything counts, right? Kelly took Sarah's hand and she took mine to walk over to a coffee shop in the mall.

"So what's up with you and Ben? I know that Rachel is curious, and a little sensitive."

"He's totally pissed at me. I told him that it seemed like he enjoyed fucking Rachel more than fucking me."

"Male egos are so fragile sometimes."

"So what's gonna happen?"

"I think we might just both agree to see other people."

Kelly turned to me before speaking to Sarah. "Maybe including our little friend Rachel?"

Sarah looked at me and smiled. "Maybe, provided she's a good girl, helps me with my math, and continues to go down on me."

"I... I'd love to." I paused and thought about what she said. "What do you mean by being a good girl?"

"Nothing you're not doing already."

"You mean dressing like this?"

"If you can do it for Kelly, you can do it for me, if you want to be my girlfriend and lover, assuming Kelly doesn't mind sharing."

"Rachel isn't my lover. I'd rather keep it that way, so if you want more than that from her, be my guest."

"Well, Rachel, does that sound good to you?"

"It's not what I dreamed of, but certainly the best offer I've had."

We ordered coffee, sat down at a table, and Rachel asked me to help her with math. Kelly sat with us for a while, then got up and said we'd catch up later. I wasn't real thrilled with her leaving me dressed up as a girl, even if she was coming back for me. Sarah said if it was a problem, she could drive me where I needed to go.

Sarah was having trouble with algebraic equations, particularly quadratic equations. I tried to explain that it wasn't that hard, but she was a little math impaired. She pulled out one of her homework problems.

"It is x squared plus two x minus twenty four and they expect me to tell them what x is."

"It isn't that hard. We just need to factor the equation. Can you think of combinations of numbers that multiplied together equal twenty four?"

"Well, let me think."

"Several combos, one times twenty four, two times twelve, three times eight, four times six."

"Yeah. And so?"

"And in one of those combos is the difference between the numbers two?"

"Four times six?"

"Because the last number is negative, one of the numbers will be negative and one positive, you you'd look for the difference between the two. If it were positive, you'd look for a combo where the sum equals the factor on the x."

"Okay."

"So the equation can be factored down into x plus six, times x minus four."

"I guess I see."

"So the solution is either x plus six equals zero, meaning x equals minus six, or it is x minus four equals zero, so x equals four."

"I sort of see, I think."

"It isn't too bad when the solution is integers."

"Integers?"

"Whole numbers."

"Okay."

"We can go over some more. Maybe you'll understand better."

About that time Sarah's phone beeped at her. She had a text and read it, then turned to me. "Kelly is going off with some friends and asked if I could drop you off at her place when we're done."

"Do you want to keep working on your math then?"

"Sure, why don't we go back to my place to work on it."

"Sounds great."

We walked to Sarah's car. She opened the door for me, which still felt weird. It will take a while to automatically think about getting in a car without showing my panties. She drove us to her place, where her older sister Suzanne had a couple of friends over. They seemed to be enjoying themselves and had some beer.

"Suzie, my friend Rachel and I are going to be in my room working on math."

"Sounds good, Sis."

About that time, a guy in Suzanne's group spoke up. "Would you girls like a little help with your math?"

"No thanks, Jeff. Rachel knows her stuff."

"Are you sure? I mean..."

"This is just algebra, and since I'm currently making decent grades in calculus 3, I think I can handle it."

"Calc 3?"

"With Professor Volkov."

"Okay. Well let me know if you need any help."

We headed upstairs to Sarah's room and locked the door. Once we were in the room, Sarah gave me a long kiss.

"After we're done with math homework, we can have some fun, if you'd like."

"For sure."

We spent easily an hour going over her math homework. I helped her solve the problems and explained the methods, as best I could. Toward the end, she was solving some of it herself, though still checking with me to see if she was doing it right. I was pleased, and she seemed ecstatic. She put up all her papers and pulled me toward her on the bed.

"That calls for a big thank you."

She lay down on the bed, pulling me down on her and we began to kiss. I really enjoyed kissing Sarah and she seemed to enjoy kissing me. She took off my top and let me take hers off. She I stroked her breasts through her bra, which she seemed to enjoy. I was happy she was interested in me, I just wished it could be me dressed as a boy.

"You think you can unhook my bra?"

"I'll sure try."

I reached behind her and fumbled a little bit, but since I had a little experience in putting Kelly's bras on myself and taking them off again, it wasn't too hard. I pulled her bra off her to look at her boobs again. I'd had a little chance to play with them last night, but not as much as I'd liked. Sarah was a b-cup, certainly not the c or d of her sister Suzanne, but I liked her boobs anyhow.

Her boobs had no sag at all, but given her age and that they were not huge, that's about what you'd expect. Her areolas were very dark and her nipples stood up already. I caressed her boobs as we kissed, before she gently pushed my head down. I kissed my way down her neck to her right breast. I paused for a second to look at it before taking the nipple in my mouth and kissing and sucking on it for an instant.

I then kissed and licked my way around her boob, working my way out from the nipple to the edge, then back in again. Once I'd made my way back to the nipple, I really focused on it, licking, kissing, and sucking on it. I'd played with her boobs a little last night, but didn't have the chance to pay this kind of attention to them. I fondled her left boob, while my mouth made love to her right one.

Sarah moaned and squirmed underneath me, and she stroked my head as I tried to give her boob the attention it deserved. After a little bit I shifted over to kiss the left one as I stroked the right. Before long, she was arching her back and humping my belly as I enjoyed her breasts. I never realized that a woman's breasts were so sensitive, but Sarah acted like this was wonderful.

"Rachel, baby, that was great. Ben isn't half as nice to them as you are. But please, go down on me again."

I kissed my way down her abdomen to her waist. I unbuttoned and unzipped her skirt. She lifted her hips and I slid her skirt and panties down her legs. She lifted her feet so I could get them all the way off and Sarah lay naked in front of me. She spread her knees wide, opening up her sweet little pussy to my attention. I kissed her on the inside of her knees and worked my way up to between her legs.

I tried to remember what I'd done and what she seemed to enjoy last night. Hell, this was only the second time in my life that I'd licked a pussy. I licked up the outside of her pussy lips on the right side till I reached the top, then moved to the other side and licked my way back up on that side. I made a superficial lick up the center of her pussy, not pushing my tongue inside quite yet.

As I did, I could see her clit barely beginning to peek out from its hood. I gave it a quick lick, then began to get my tongue inside her pussy. I kissed and licked and tongue fucked her till she asked me to put a finger in her too. I slid a finger inside her as I started to kiss and suck on her clit. I moved my finger in and out. She was really wet and it slid in her with ease.

Sarah began to hump my face and finger as I continued to finger her and suck on her clit. She started to moan so loud, I was afraid Suzanne or her friends would hear, but she'd wrapped her legs around me so I just kept licking and fingering her until she came. I had taken my other hand around and was massaging her ass as I enjoyed her pussy. As she came down off her orgasm, she unwrapped her legs from my head and pulled me back up her.

"Rachel, get naked for me."

I had previously kicked off my shoes, and Sarah had pulled off my top, but now I took off my skirt and panties as Sarah unfastened my bra. Sarah rolled me onto my back and rolled on top of me. We kissed as I felt her nipples scratching my chest and felt my prick sawing between her legs just below her pussy. She moved down just a bit and grabbed by cock and guided it into her love tunnel.

She eased it slowly in, and while I wanted to just ram it in there as fast and hard as I could, I let her work it in an inch at a time until she was tight up against me. She began to move her hips a bit to the left and right which moved me slightly in and out of her. Then she pulled way back until only the head was in her, and pushed hard back in.

I kissed her as I played with a boob with one hand and her ass with the other hand. She fucked me slowly, gradually picking up speed until she was like a machine driving my dick deep inside her. I could feel it building up and kissed her as I moved both hands onto her ass. As I started to cum, I grabbed her ass and held her tight to cum deep inside her pussy.

This was only the second time I'd had a chance to fuck this girl, and I couldn't imagine anything in life that could possibly be better than what I felt with Sarah. The Earl of Chesterfield said of sex, "the pleasure is momentary, the position ridiculous, and the expense damnable." In my case, the expense was dressing as a girl, which I didn't care for, but it was totally worth it as far as I was concerned.

Sarah lay on me and we kissed as I stroked her back and ass, while my cock slowly shrunk in her sweet little pussy. All I could think was that heaven should be half so good as making love to pretty Sarah. Finally my dick eased out of her and we rolled onto our sides and continued to kiss and stroke each other.

As we lay there, I heard someone try to open the door, which we had wisely locked. The knob rattled and Suzanne spoke through the door.

"Sarah, we're having some pizza. Get some clothes on and send your girlfriend home."

"Okay, Suzi, we'll be right out."

I got out of bed and put my panties and bra back on as Sarah began to dress as well.

"So she knows that we weren't just studying?"

"She isn't stupid, and I've had Ben over here, and she's had guys and girls over too."

"Girls, too?"

"I don't intend to share you with her, so calm down."

"I... didn't think..."

We finished dressing. Sarah had an attached bath and I went in there to brush my hair and touch up my makeup. Sarah came in and gave me a hug and we kissed before she brushed her hair. We came out of the bathroom holding hands and kissed a bit before unlocking and opening the door. No one was in the hall, but we could hear Suzanne downstairs.

"The pizza's getting cold. Get your butt down here."

We came downstairs and Sarah walked me to the door. We stopped and kissed, before she patted me on the ass and shooed me out the door. As I got outside, I realized Sarah had driven us there, and my car was two miles away. I got my phone and called Kelly.

"I hate to ask you this, but can you pick me up from Sarah's place?"

"What's up? Did it go that badly?"

"No. Suzanne wanted Sarah to eat dinner and she sent me out the door before I realized I was stranded."

"You're lucky. I was about to head back to school, but I'll swing by and get you before I hit the road."

I waited outside for about fifteen minutes until Kelly pulled up. I opened the door and hopped in, though I almost showed my panties again as I did. She drove back to her place, and was curious about what happened.

"So was it just the two of you, or did anyone else get involved?"

"Luckily, just Sarah and I."

"Spent quite a while at it, so it must have been good."

"It was wonderful. I just wish I hadn't had to dress like this."

"Come on. You were getting off dressed like this before I caught you."

"Yeah, but it was different."

"Then you didn't have a real girl to get it on with."

We got back to her place and she simply let me out. I had a key, so I let myself in her house as she left for school. I cleaned off the makeup and changed back to my boy clothes, except for the panties she made me wear over. I drove the short distance back to my place and went it. My mother took one look at me and shuffled me off to another room.

"Is there some particular reason you have nail polish on your fingernails?"

Shit, I'd forgotten to take it off. "Mom, I was with this girl, and we were doing things, and she thought it would be fun to paint my nails. I forgot about it when I left."

"Is that ALL she made you do?"

I hesitated. I didn't want to tell her I'd been dressed and made up as a girl for most of the day. She looked closely at my face.

"Your eyebrows were plucked or shaped."

"Yeah."

"What else did she do?"

"She painted my toenails too."

"That's why you were fully dressed with shoes this morning."

"She did that yesterday and told me not to take it off."

"What else? I'm your mother, I can read you. I know there was more."

I knew she knew that there was more to it. "She made me wear a pair of her panties."

"And you still have them on, don't you?"

I could feel my face get hot and I knew I was blushing terribly.

"It was a girl you were with - a real girl, right?"

"A real girl, with all girl parts."

"And you and she?"

"Once I did what she wanted, she let me make love to her."

"I'll get you some nail polish remover. Get that off before you come to dinner."

Yes, ma'am."

I ducked in my bedroom, took off my shirt, pants, and the panties and had just put on jockey shorts when my mother came in the room with the nail polish remover. She looked down at the panties lying on the floor and frowned. I'd taken off socks and shoes to take off my pants, so my toenails were pretty apparent too.

"Lift your arms."

I lifted my arms, though I knew what she'd see and say.

"You shaved your armpits and legs too?"

"I did."

"Were you in a dress or a skirt?"

I was feeling about as humiliated as I possibly could. "A skirt."

"Don't ever let your father know about this."

She turned and walked out. I dressed, removed all the nail polish and stayed in my room as much as I could for the rest of the evening. I got a text from Sarah, saying she would like to see Rachel after school tomorrow. This was clearly going to be a regular thing, as long as I saw Sarah.

...

After classes the next day, I went and checked on Kelly's house, as I usually did, then dressed and made up as Rachel to go see Sarah. I drove over there and rang the doorbell. Suzanne answered the door and let me in.

"You're here to see Sarah."

"Yes."

"What was your name again?"

"Rachel."

"You look familiar. I'd swear I know you from somewhere."

"I came with Kelly to the party the other night."

"Before that."

She looked at me carefully, and I began to get nervous. About that time, Sarah came downstairs and saw me. She came over, hugged and kissed me, then took my hand and led me toward the stairs. Suzanne kept looking at me the whole way, which made me nervous as hell.

jackie_em
jackie_em
1,558 Followers