tagTransgender & CrossdressersRich has an Adventure

Rich has an Adventure


This has some sex, but not a lot. It includes cross dressing, and sex with both male and female, along with reluctance in the cross dressing.


It started when my neighbors took a long winter vacation to Florida. They had a condo down there and kind of felt like they wanted a break from the chilly northern weather. I am Rich, a 20 year old guy who lived a few doors down from them. I was attending community college in town while working part time to pay for it.

My parents didn't have the kind of money that the Jacobson family did. We had a much more modest 3 bedroom, 2 bath house, compared to the 2 story, 4 bedroom, 4 bath house with double garage and pool that the Jacobsons had. They had a security system on their house, but felt they wanted someone to check on their house regularly while they were out of town.

They were willing to pay me to check on their house, and I was more than happy to do so. I was expected to go over every day, make sure everything was fine, check their aquarium, feed the fish and clean it if necessary. So many things can go wrong in a house and on a previous trip, they'd had a plumbing leak that cost thousands to fix and forced them from their house for over a week when they returned.

So basically, pretty light duty. I just had to check the whole place daily and make sure everything was fine. They had a daughter, Kelly, about my age who was off at a big university. Once in a while, she would come home on the weekend, but since her school was 150 miles away, she never was home during the week.

Kelly was a very pretty girl, about 5'6" and 125 pounds, with a nice shape, a cute face and c cup boobs. She and I had gone to school together, but ran in different social circles. She was one of the popular kids, while I hung with the other geeks and nerds. She was never snotty toward me, but it was clear that she was hot and I just wasn't.

Now, I kept myself in decent shape, mostly with running, but I was kind of short and not at all muscular, nor did I think I was particularly good looking. I was 5"6" and about 135 pounds, still waiting for my facial hair to come in. My hair was a little long, and I occasionally had someone mistake me for a teen age girl, which embarrassed me.

So, I checked on the neighbor's house every day, going from room to room, making sure there were no problems anywhere. They had given me a key and a code for their security system. Their house was kind of a respite from my own place with my parents constantly bickering and expecting me to do all sorts of things for them. Plus, I had an 18 year old sister, Julie who was really a pain. So I would do a lot of my studying in the neighbor's house.

It was quiet in the house, since I was there alone and I could take my laptop and connect to their wifi, which made studying and schoolwork so much easier. I had always had kind of a fascination for Kelly, though as I said, she had zero interest in me, and that led me into some foolishness.

I had to check all the rooms in the house, which of course would include Kelly's bedroom. At first, I just checked it out, but after several days, began to look at her clothes. As I said she was away at school, but still had lots of clothes at home. It started pretty innocently with just touching her skirts, dresses, and tops, then progressed to touching her panties, bras, and lingerie.

I was all alone in the house and soon took to stroking her undergarments as I masturbated in Kelly's bathroom. I'd put everything back, of course, and tried to make sure not to soil anything. Occasionally, I'd slip up, but then would wash and dry the items before I put them away. After a while, I went a little farther.

I was only a little bigger than Kelly, so I tried putting on some of her clothes when I got myself off. That was a lot more thrilling than just touching her clothes, and I had great fun doing that. I'd take my longish hair and brush it in a more feminine style, put on Kelly's clothes and prance around her room before getting myself off.

It was pretty stupid and immature, but I was shy and none of the girls I knew had any interest in me - not Kelly and not any of the others either. It seemed like innocent fun and a way to satisfy my own sexual urges. I probably did that for a couple of weeks. Since the whole family was gone, I felt safe doing that. I wasn't as safe as I thought though.

I went over to their house one Saturday, and did a cursory check of the house. Everything seemed fine, so I went to Kelly's room and dove into her clothes. I stripped off my clothes and put on a pair of lacy pink panties along with a pink bra, and stuffed the bra to make it look like I had boobs. I got a cute skirt than was only halfway down to my knees, put on a cute top and some low heels.

I went down to the kitchen to get something to drink and came back to the bedroom. Something looked odd and it took me a minute to realize that my clothes were not where I had left them. I knew I had taken them off right by Kelly's closet, just dropping them on the floor, but they didn't seem to be there. I couldn't imagine where they'd gone when I heard a sound.

I turned around and there was a flash of light. Kelly was standing there, and she'd just taken a picture of me wearing her clothes.

"Wha... what are you doing here?"

"This is my house. I live here, and this is my room."

"I didn't think you..."

"That's pretty obvious. I can't imagine you'd have put on my clothes if you expected me to be here."

"Please, don't..."

"Don't what? Don't tell anyone? Don't show them the pic of you in drag?"

"Please. I beg you."

"I don't have to tell anyone. I also don't have to give back your boy clothes."

"God. Please Kelly. Don't make me go home dressed like this."

"I got the feeling you enjoyed dressing like that."

"Only in private. No one has ever seen me like this."

"At least until now."

"Please. What do you want? I'll do anything."

"You just might."

Kelly walked over, looked closely at me, and stroked my face. I had little or nothing in the way of facial hair, and was trembling at the thought of what she might expect of me. She took my hand, led me over to a chair and sat me down.

"You aren't much as a guy, but you make a cute girl."

"But I'm not a girl."

"Funny, you look like one to me."

"Kelly, I'm sorry I put on your clothes. I just want to change back and go home."

"Not so fast, girl. You said you'd do anything. Are you ready to find out what anything means?"

"What did you want?"

"Hair isn't bad, but it needs some tweaks. You need some makeup and nail polish, along with some better grooming."

"Makeup, nail polish, grooming?"

"We need to get rid of that nasty leg hair and underarm hair."

"Please don't do this to me."

"Okay, just leave, right now."

"I need my clothes."

"No, if you leave without doing what I say, then you can wear that home."

"I can't go home like this."

"Then you'd better do what I tell you."

"Why are you doing this?"

"You violated me, by wearing my clothes, by jerking off while wearing them."

"How did you know I...?"

"Security cams in the house. I have some lovely video of you prancing around in my clothes and then masturbating while wearing them."

"I never thought..."

"A bright boy like you should try thinking once in a while."

"And your security system has videos of me?"

"I saved those out to a cloud server, along with the pic of you from a few minutes ago."

"What are you going to do with them?"

"That depends on whether you do what I tell you."

"I guess I don't have much choice."

"That's the spirit. Now call your folks and tell them you're going out with some friends."

"I... I never go out with friends."

"Convince them you're going to be out for a while and they shouldn't worry."

I called home and told my mother that I had a paper for school and that I was going to the library, then would be comparing notes with some of my classmates. Mother seemed happy that I was doing any socializing and told me not to worry and get home whenever I could.

Kelly made me take off her clothes, then shaved my underarms, and put depilatory on my legs and my little bit of chest hair. She had me shower off and I was mostly hairless from the neck down. I put the panties back on tucking my penis between my legs and put on the bra with some stuffing. Kelly dried and styled my hair, trimming it a bit in places, but didn't let me see how it looked.

She painted my fingernails and toenails and made me sit very still while the polish dried. She put a bright red polish on them, and shaped the fingernails. While I sat waiting for the polish to dry, she started messing with my eyebrows, shaping them, as I later realized. She then put some foundation and blush on my face, along with eye shadow, mascara, eyeliner, and lipstick.

When she was done, she had me put the skirt and top back on, along with the open low heels. Luckily for me, they were wide heels, so it was easier for me to stand and walk in them. Once she was finished, she took me to a mirror and let me look at myself.

"See, Rich, I told you you made a cute girl."

"Are you done, then?"

"Not even close, girlie."

Kelly took a few more pictures of me in full dress and makeup, though it was hard to recognize me as the nerdy little guy who looked after their house. She changed and did her own makeup. I looked around as discretely as I could, but didn't spot my boy clothes. I had no idea where she put them, and knew I had to get them back to go home.

"Well, Rich. Now you and I are going to go party."

"What? Where?"

"A friend of mine is throwing a little party, and you and I are going there."

"Just let me change back and wash off this makeup."

"Not a chance, girlie. You're going exactly like that."


"You want to dress like a girl, you can see what it's like being one."

"People are going to see me like this?"

"Don't worry, girlie. I doubt anyone will recognize you. Just keep your voice higher pitched and breathy."

Kelly had parked down the street, which was why I hadn't realized she was home. Apparently, she knew my route in checking out the house and ducked from a room I hadn't checked into one I had, when I was in another room. I had to walk down the street with her to her car. Of course, we ran into another neighbor, Frank, who was walking his dog. He had to stop to talk to us, so Kelly stopped, though I wanted to get away. There was no chance of escape, not dressed as I was, so I stopped.

"Hey there, Kelly. I didn't realize you were back in town."

"Just in for the weekend, then I'm back to school."

"Who's your pretty lady friend here?"

"She's a girlfriend of mine from school. Rachel and I are off to a party."

"Rachel, I'm very pleased to meet you. My name's Frank. I hope you come back with Kelly more often."

"Nice to meet you Frank."

"Wish I was going to that party. I'd love to get to know you better."

Kelly was teasingly stern. "Now, now, Frank. Your wife wouldn't appreciate that."

"Believe me, I wouldn't tell."

"We have to get to the party now. Talk to you later, Frank."

"I sure hope so. Nice meeting you, Rachel."

"Thank you."

I was almost shaking as Kelly took my arm and walked me on down to her car. Clearly, Frank didn't recognize me, but I guess I didn't look at all like Rich any more. We got to the car and Kelly opened the door for me. I sat down, and quickly realized that I needed to sit differently in a skirt or anyone passing could see my panties. Kelly got in the car and started it.

"Where are we going?"

"Suzanne Lopez. Her parents are out of town and she's throwing a party."

Suzanne had been the head cheerleader her senior year in high school and was one of the most popular girls in school. I think she'd even been homecoming queen. Her parents had a huge place a couple of miles away. I think her dad was some hotshot business executive. He made big bucks and often went out of town on business trips with his wife this time, apparently.

There were rumors of Suzanne's dad having affairs with several women, mostly women at his company. Often there would be some reason they would have to accompany him on one of his business trips. No one had any doubt what kind of business they were involved in during those trips. Still, Suzanne was pretty hot stuff, and not the social circles where I'd be welcome.

Kelly parked and I opened the door to get out. This time I kept my knees together as I swung my legs out of the car. Definitely weird feeling, since I'm use to swinging one leg out then the other. Not sure I was completely successful at being modest. I saw a guy nearby looking at me and grinning. I felt my face get red as I stood up to get out, then smoothed my skirt back down.

"Do I really have to do this?"

"Not at all. You could just walk home from here. It isn't that far."

"But in these clothes?"

"I think you look very pretty."

"I feel stupid. And what if someone figures out I'm a guy in girl's clothes?"

"We'll just have to make sure that's not a problem."

"How do we do that?"

"Leave that to me, Rachel, dear."

"So I'm Rachel for tonight?"

"If we call you Rich, someone might figure things out. You don't want that, do you?"

"Hell, no."

Kelly took my hand and began walking me toward Suzanne's house. As we did, we ran into Rob, a guy from our high school class.

"Hey, Kel, nice to see you back in town. Who's your cute friend?"

"She's a school friend, Rachel. Rachel, this is Rob."

"Rachel, it's so nice to meet you. Kelly's been hiding you. That's not nice, Kel."

"Get over yourself, Rob. Just because you drool over every cute thing in skirts, doesn't mean I have to introduce everyone I know to you."

"Well, Rachel, I hope we get a chance to spend some time together tonight."

"Bag it, Rob, she's not letting you into her panties, no matter how hard you try."

"Can't fault a guy for trying, can you?"

"Rachel, fair warning, Rob will fuck anything in skirts that'll hold still long enough."

Kelly got us away from Rob, which let me breathe a little easier. I knew Rob from high school, but he clearly didn't recognize me. I'd just as soon keep it that way. I sure didn't want him trying to get into my panties. Shit, it was bad enough being in panties and a skirt. I sure didn't want guys hitting up on me.

We went inside and Kelly was swarmed with all her high school in crowd. Way too many of them, particularly the guys were much too interested in me. Someone handed us something to drink, some kind of punch, it tasted like. What I didn't realize at the time was that the punch was spiked. Kelly broke us loose from the gaggle of friends and introduced me to Sarah, Suzanne's little sister.

Sarah was 18, and cute, just not the knockout that Suzanne was, or Kelly for that matter. Sarah was about 5'4" and 115 pounds with a sweet face, brunette hair in a shoulder length bob, a nice shape and small boobs. Being Suzanne's little sister, Sarah always had an in with the popular kids, though Sarah herself was a little shy.

Sarah was there with her boyfriend, Ben, who was a little older than me, about 6' tall and 170 pounds and looked like he spent time in the gym. Kelly whispered something to Sarah, who giggled and nodded, then looked at me and smiled.

"Rachel is kind of shy. Can you two keep an eye on her and chase away all the guys who only want something to screw?"

Sarah looked at me before she replied. "I think we can manage that."

Kelly gave me a peck on the cheek. "Rachel, I'm going to socialize a bit. I'll get you when it's time to leave." Kelly then turned and walked off into the crowd at the party. I'd kind of been hoping that I could stick as closely to Kelly as possible, but that obviously wasn't going to happen.

There was music playing, and Sarah turned to me. "Rachel, let's dance a bit to loosen up. Ben you can watch our drinks or just dance with us both."

I didn't think I wanted to dance with Ben, but he and Sarah were a couple and Sarah wasn't going to ditch her boyfriend to babysit me. There was one area close to where we were where folks were dancing. Sarah led me there by the hand with Ben trailing. The three of us more or less danced together, though I tried dancing mostly with Sarah, she turned me toward Ben a few times.

A few guys tried to join us on the dance floor, but we stuck pretty much together, and tried to wave them off or ignore them. After a bit, they tended to give up. A slow number came up and Sarah grabbed me and pulled me close to dance. I'd never danced like this with a girl before and the combination of holding her close and her perfume were intoxicating.

As we danced, I could feel my cock starting to get hard, and I tried to shift positions so that wasn't quite so obvious. Sarah pulled me tighter and I was really concerned, then Ben cut in. I thought he would dance with Sarah, but instead, he grabbed me to dance. He pulled me tight and I was scared shitless. If he felt my cock, what would he do?

As we danced, Ben let his hand wander down over my ass. I was embarrassed as hell, but didn't know what to do without making a scene and alienating the two people who were acting as my chaperones. He rubbed my ass, as he bent his head down and starting nibbling on my earlobe. I didn't want some guy to be doing that to me, but found it all was starting to turn me on.

The song ended and Ben kissed me on the lips before we went back to where we'd been. Sarah was there waiting as Ben walked me back with his hand on my ass. When we got to where Sarah was, she asked Ben to go get us all some drinks. I breathed a sigh of relief as he walked off, and that was pretty obvious to Sarah.

"I'm sorry Ben was pawing you."

"It was just kind of a shock. I'm not used to guys doing that."

"At college, I'm surprised you haven't gotten that and a lot worse."

"I don't slow dance with guys."

Ben brought us more drinks and I began to loosen up, though I only later realized it was from the alcohol. We talked about school. Sarah was a freshman at the community college where I went. Ben was a little older and had gotten a two year certificate degree and gone to work. I began to realize that Sarah and Ben were not doing all that well as a couple and might break up before too long.

I told her I was an economics major and working on my four year degree. Sarah was thinking in terms of something in the social sciences and planning on her four year degree. Sarah and I talked about courses and professors, and it seems she was taking a math course, but struggling with it, since she was slightly math impaired.

Being an economics major, I had to take a fair amount of math and did pretty well at it. She asked if there was any way I could tutor her and help her through that class. I agreed, not thinking, then realized that she'd expect help from Rachel, not Rich. I must have looked concerned, and Sarah leaned forward to whisper to me.

"I'm guessing you don't normally look quite like that at school."

"No, not exactly."

"That's not a problem. I can use the help whichever way you dress."

"Do you mean...?"

"It's okay. Kelly told me and I'm good with it. Besides I could feel your thingy while we danced."

"I don't normally..."

Ben seemed to be watching a really sexy blonde, as Sarah gave me a kiss. I tried to return the kiss, but wasn't even sure how to react. Sarah sent Ben off for more drinks before getting close to me.

"What do you call yourself, when you aren't Rachel?"

"My name is Rich. I was a year ahead of you in school. Same class as your sister and Kelly."

"What made you start dressing this way? Is it something you've always felt or wanted? How long have you been doing this?"

"I'm watching Kelly's parents' house while they're out of town and she's away at Uni. I tried on some of her clothes as a cheap thrill. She caught me in her clothes."

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