My Summer as a Girl Pt. 01

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College intern is forced to cross dress for grocery money.
4.4k words
4.6
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Part 1 of the 7 part series

Updated 06/09/2023
Created 06/04/2018
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Let me give you my bio real quick. Not sure if it explains anything or not. I grew up in Iowa. My dad sold tractors, trucks and used cars, depending on the year. We moved around a couple of times, and I never really fit in at the schools.

Not sure that I would have if I had stayed in one place either. See, I'm kind of a nerd. I'm pretty shy, like computer games, and I read a lot. Yeah - stereo-typical geek. No sports, few girlfriends, OK only two. But when I graduated from high school, I knew things were going to change!

Yeah - that was stupid. Of course they didn't change. I was still a geek. I spent my first year at that huge state school, living in the dorms. I'm sure people would say I was bullied, but it wasn't anywhere near as bad as it had been in high school. I mean, most of these guys would get drunk and stupid, maybe get stupider, but most of the time, they had more important things to do than pay attention to me.

My roommate was this metrosexual (do we still use that term?). He had some big titted girlfriend who's dad was a doctor. He spent most of his time sleeping at her place. It seemed he only came "home" to shave his chest and do other creeping grooming things that probably would have grossed her out. So for better or worse, I pretty much lived alone.

Don't think this was all horrible. I had some friends. We'd eat together when our classes allowed, and played a little D&D on the weekends when we could. I was actually pretty content.

As freshman year was ending, I saw a sign up in the Business Building: Internships were now open to all students. This was a pretty big deal because normally only upperclassmen could get internships. So I went over to the office to see what was available. A lot of the better ones had already been taken, but there were still a couple dozen openings, including three in my business admin major.

I talked to my folks for a while that night. The one I wanted was with a company in Omaha. That would mean not going home for the summer. But my aunt lived in Omaha, so I could "afford" to stay there if she'd let me crash. My parents were all "This is the best for your career, so you have to do it", so I did. I went in the next morning and talked to a guidance counselor.

Miss Patsy Ignozzio was really nice. She made me feel like I was doing her a favor by taking this internship. She said it made the school look better, like they hadn't wasted the company's time in offering the job. The pay was crap, the work was menial, but I was going to get two classes worth of credit for it, and some real work experience. I told her to sign me up.

I basically packed my dorm room into my tiny car and went straight from school to my Aunt Janey's after exams. Looked like we were going to get along as well as we normally did. You see, my aunt's only 34, ten years younger than my Mom. I always loved being with her, because she's the opposite of me. She's loud and fun and crazy. If I was afraid of riding the roller coaster at the state fair, she'd drag my ass into the car and then scream without ever hanging on. If I wanted to wait in line for an hour waiting to get one of those cream puffs, she'd wait with me, cracking jokes the whole time and then insist that we both get two. Then she'd eat one without using her hands.

But now, after a year of college and being 19, I kind of looked at her differently. OK, she looked like an Iowa farm girl, but in the best ways. She was built like a brickhouse. She startled me when I first got there by coming out to help with the luggage. Her coming to help wasn't surprising, it was the Daisy Dukes and tank top. She was hanging out of clothes. If she hadn't been my aunt, ... well, probably nothing, but still, she looked hot.

So I settled in with my aunt and went to orientation the next day. It was pretty weird. The company had 44 employees, yet they had hired eight interns. We were all going through the orientation together, and we sort of started to get to know each other. Every night I'd go home to my aunt and she'd ask me how my day was. I couldn't tell her, because I didn't know. Everything seemed strangely depressed at the company.

I figured it out the second week. Well, I didn't figure it out, they just told me. They told me the company had filed for bankruptcy and they weren't going to pay us even the meager wages we thought we would get. That's why they had so many interns. They had hoped to cut payroll expense by using us. Great! Looks like I was headed back to small town America once again.

I told you that whole sob story to explain where I am right now. 1:30 in the afternoon on a Tuesday and I'm in my aunt's driveway rehearsing what I'm going to say to my parents tonight on the phone. But Aunt Janey's car is in the garage. You know, come to think of it, I didn't know what she did for a living. She was always still home when I left and was home before I was.

Kind of interested now in how she was employed, I walked into the house, put my stuff down like I always did and headed to my room. I checked the kitchen, no Aunt Janey. I checked the basement where she had her work out stuff, nope. So I headed to the bedroom she let me use. It was to the right as you came up the stairs, while her room was down the hall to the left, just past the bathroom. Her door was ajar, and it sounded like she was on the phone with someone, like a speaker phone, but I couldn't understand what they were saying, and I honestly don't think I was all that interested.

After changing, I figured I should let her know I was home, but as I passed the bathroom, I figured nature's call was stronger. I went in there and closed the door behind me. Sitting down I could hear her conversation better now. My eyes went huge and I sort of freaked out.

"Do you like that?" she was saying. "Do like the way my pussy drips when I'm talking to you? She doesn't do that for anyone else, just for you. Oooh I wish you were here to fill me with that big pecker of yours. Yeah, fist that pecker. Imagine that you're burying it deep inside of me. Oh, I can feel it. Can you feel it inside of me?"

So, yeah, DAMN! I finished what I was doing and snuck up to her door. She was sitting on the edge of her bed, naked except for a flimsy robe that was wide open. She was talking to someone through her laptop. I couldn't hear him too well, but I caught a glimpse of him on her screen. He was some old guy, with his really old cock in his hands, jacking it like there was no tomorrow. She kept encouraging him, "Come on, baby. Give me your load. Picture it hitting my titties right here." She was stroking the valley between her tits and just pouring it on.

I didn't see it (thank God) but I heard him cum in grunts and groans. When he finished, she encouraged him some more but was clearly saying goodbye. As she closed her computer, she somehow realized I was there.

"Holy shit!" she screamed at me. Her hands went to her mouth like an old time movie actress, and she ran to the door. It seemed really odd to me that she ran to me, opened the door and grabbed my hand. She pulled me to the bed and sat me down. "How much of that did you see?" she asked. At no time had she tried to close her robe or cover herself or anything like that. She was talking to me with those big hooters standing right in front of me.

"I guess I saw enough," I said. I don't know what I was thinking, but part of it must have been some kind of disappointing judgement, because she went from being worried about me to being frustrated with me pretty quickly.

"What are you saying Brian?" Oh yeah, I never told you my name. I'm Brian - good to meet you.

"Is that your boyfriend? He's like 80."

"No," her voice had taken on this serious tone that sounded too much like my mother. OK, her sister, but still. "He is not my boyfriend and he is only 48. Do you think you have a right to disapprove?"

Well, she had me. I was disapproving, though I don't know why. At what point did it become my business what she did on the internet? I was looking down all sheepish when she continued. "Seems pretty shitty of you to judge me after living in my house rent free and eating my food without paying for groceries."

This was my Aunt Janey, who I loved. I knew that. So, I looked her straight in the face, and I told her the truth. "Aunt Janey, I think I'm a little jealous of that guy. I'm not trying to be a dick, but he got one hell of a show, and I'm feeling a little protective and a little jealous."

She reached out her arms and hugged me, long and hard. I think she was catching herself and not crying. I hugged her back. I'm not the smoothest guy, so for some reason, that was when I told her, "Oh, and I was fired today."

Well, I guess I'm a little too honest for my own good. I had told her my true feelings and I had told that I was fired. You don't want to hear all the mushy stuff nor all the talk about money. You see, Aunt Janey was doing OK, but she couldn't support the both of us. She had been trying to find a way to tell me I had to start putting in some money - at least to buy my food.

Truth is, we got drunk that night. She was robbing from Peter to pay Paul and she wasn't sure that there was going to be enough money to buy beer the next time. So we drank her last seven beers and the bottom half of a bottle of Jack and sort of passed out in the living room. The next morning, neither of us had anything to do, so we hit the hair of the dog and started in an old bottle of rum she had.

She opened the computer to read her emails, hoping she had a "date" - a paying date. Sure enough, the same guy from yesterday had sent her an email. Maybe she didn't close the laptop fast enough or maybe I was more visible than I thought I'd been, but he was under the assumption that there was another "girl" there and he wanted to see the two girls together. Said he'd pay double so we were both compensated.

When you start to wonder if you have enough money to buy dried noodles, you start thinking differently. Oh, I'm sure the rum helped! Of course, I said "no!", but Aunt Janey started talking. She's always been able to talk me into things I didn't want to do. Scratch that. She's always been able to talk me into things I wanted to do but was too scared to try.

What was she suggesting? That we spend today with her taking extra special care of me. She was going to clean me up, do my hair, spend time with me, and then tonight, we'd both appear on the screen for the old guy. We'd have to kiss, and I'd have to have my hands all over her chest, but she was sure that would be all we'd need to do and then we'd have money for groceries. She was sure it would only be the one time. We were both naive enough or drunk enough to sort of believe that.

I took a nap and she ran out to the store (probably shouldn't have been driving!). She woke me up and had me drink some more rum. Yeah, this might have been a really stupid idea, but if we were going to go with it, liquor was going to be needed.

I guess I never told you what I look like. I'm thin. I guess I'm short - I'm about 5'7". No, there's really nothing too masculine about me, so I hate to admit I know why the guy on the screen thought I was a girl. I think I was even wearing a pink golf shirt. But I couldn't pass for a girl, unmasculine or not.

Well, I guess Aunt Janey is smarter than I gave her credit for. She saw things in a way that I didn't. I need to explain something here. I'm not gay. It's not even a close call. I like girls! But I'm not some big swarthy caveman that demands women treat him a certain way. I am mild mannered. My fingers are a little too long and too thin. OK, my cocks probably the same, a little long, but too thin.

My Aunt Janey was all woman, but not completely by birth. I mean that she really knew how to accentuate her best features. She had great tits, so when she maneuvered the camera, it mainly hovered there. She told me she used makeup on her breasts to make them look smoother and creamier. Now she was going to use some of that magic on me.

I was still buzzing and she wasn't going to let me sober up. She started by shaving my legs, but when they still looked dark, she used that hair removing cream. I get that she's my aunt, but having her rub first shaving cream and later hair removal cream on my legs; it felt really good. She shaved my face too. I guess my dirty blond beard looked OK to her after being shaved.

There was nothing she was going to be able to do about my lack of tits, but she was a true show-woman. She found a bustier that didn't fit her anymore and put me in that. It still didn't pretend that I had a chest, but it distracted from the fact. The weirdest thing she did was when she used the hair removal cream on my backside. I got really embarrassed because I got really hard when she was rubbing it between my cheeks.

There was nothing to be done about my cock either, so she had bought me a special thing. It was flesh colored to begin with, and my cock went into that. Even though it was like a thong in the back, it contained my cock and the color kept it from showing, even if I did get a little hard. Aunt Janey said I had a sweet ass, and the guys were going to go nuts for it. She said it was meaty without being fat.

By the time she was doing my makeup, I was in heaven. How many guys get to have a gorgeous woman spend an entire day trying to make them look pretty. At every turn she was complimenting me, touching me, making me feel confident and admired. Maybe you're some God's gift to women, but I'm not. This was certainly a first for me!

Honestly, I don't know where the day went. The next thing I knew, the sun was starting to set and I looked like a young woman with a buzz cut. Aunt Janey went into her closet and got out a big hat box. Inside was a cute red wig, kind of like the mermaid girl's. She said it was from a Halloween costume, but I sensed there was more too it. Still, she used some special tape and got it properly situated on my head.

I looked at myself in the mirror and I blushed. I may not have been the prettiest girl in the world - I wasn't even the best looking girl in the room, but I did look like a girl. I knew who I was, but anyone else would have thought I had a sister, and she was cute.

Aunt Janey did some last minute coaching, including, try not to talk, and we opened the laptop. There was James. Looking at him from this close, I could see he didn't look 80, like I said he did yesterday. I guess he was just sort of normal looking.

"Whoo! That is quite a little friend you have there, Janey," he said obviously glad to see us. He probably wasn't sure he was going to get both of us to show up. "How old is she?"

Aunt Janey positively cooed at him, "She's old enough you little perv. Isn't she sweet though?" Aunt Janey seemed to have put on a Southern accent or maybe just stressed her own rural roots. I guess this was her flirting voice.

"What's her name?" he asked.

"I'm Molly," I sort of whispered at the screen. You could tell he hadn't heard me. "Molly", I blurted out more loudly. He had now heard my voice, and didn't seem any the wiser.

Aunt Janey kept up the charm and flirtation. "Now James, this is Molly's first time. Really, her first time online and her first time with a woman. Are you really interested in seeing us together, because if you're not, she's going to move her little innocent self right out of the screen?"

"NO!" he practically screamed at the camera. "No, I want to see the two of you together. This will be a very special date."

"Well, then, sugar, you know I'm going to have to charge you more to pop her webcam cherry."

"Yeah, sure, double, OK?"

"James," I heard that Mom voice coming out again, "triple." At that, she ran her fingers down my neck and down the front of the bustier. Yeah, he went for it.

Aunt Janey talked some less than romantic details with him, all the time layering in those flirtatious tones. When she asked him what he really wanted to see, he wasn't sure. Like a dog that chases cars, he had no idea what to do when he actually caught one. So she maneuvered the laptop camera at the bed and told him to hold on tight.

Don't judge me. Yes, I was sitting on the bed dressed as a girl. Yes, I was about to make out with my aunt, but she's not old, and she looks great. Yes, there was a horny almost 50 year old guy watching us through the camera, but Aunt Janey had made me feel so special, so loved, so desired all day long, I was just perfectly in the mood for some fooling around.

She had me lay down with my head closer to the foot of the bed, towards the camera. Then she leaned in and started to kiss me. It was sort of like a dream, where you are and aren't yourself. Maybe it was like an actor in a play. Sure he's married to someone else, but right now, today, he's playing a role, and it's OK that he's kissing some other girl. She kissed me slowly, and I savored every move of her tongue in my mouth. My hands went to her hips and I was holding her loosely, not guiding, just holding on. She was in charge, but she knew what she was doing.

She was wearing this really hot outfit. It was kind of like a bustier but it had an attached thong for a bottom. After we kissed for a while, she got off the bed and made like she was repositioning me, but I saw that she was just showing him her nearly bare, thong butt. When she got back into the bed we were both kneeling facing each other. We did some more kissing, and then she took her breasts out of the cups. I immediately began sucking on her nipples; all thoughts of this being my mother's sister were gone.

She began playing it up, like she had yesterday. "Oh, I love how your tongue feels on my nipples. Oh, suck those little bitches. Suck on my tits. Oooh, bite them harder." I was getting into it. I assume James was too, but I wasn't paying any attention to him. I was doing exactly what she told me to do.

While she was calling out all sorts of instructions to both of us, she took my hand and guided it down to her crotch. Like I said, I wasn't thinking any more. We had said we wouldn't go this far, but she was clearly changing the rules. As she was asking James if her liked seeing a young girl invade her private little pussy, I was sticking my fingers up inside of her, feeling how soft and warm she felt from the inside. I don't know what liquid silk feels like, but I swear that was what she was: soft, silky, and wet.

I got a little distracted by James breathing so hard into the camera, but I got over it. She called over to him, "Now dear, don't you go blowing your load just yet. You have to let me cum first. You want to see that right? You want to see Molly bring me off right here, just for you?" My fingers were flying over her clit. I was so turned on the only thing I cared about was making her cum and watching the orgasm wash over her face. My aunt was smarter and better able to keep her wits, so she kept him engaged with us.

"Eat her out!" he demanded over the screen. "I want to see you eat her out!"

Part of me wasn't sure. This was really beyond what Aunt Janey told me we were going to do, but she was guiding me off the bed. I knelt in front of her as her legs straddled my face. She adjusted the camera to get a better angle and I began licking her and sucking on her clit. My tongue loved the roughness of her clit and the smoothness of her pussy. I felt like I was hypnotized, but I just didn't want it to end. Aunt Janey was keeping up some of the conversation with James, but she was clearly getting close. Her breathing was ragged, and she had to stumble over most of her words.

James was pounding himself furiously, and I was eating my aunt the best I knew how. Suddenly, her thighs crushed in on my ears, and despite the legs in the way, I heard her scream out, "YES! YES! YES!" She was thrusting her hips into my face and I was trying not to get thrown away. James was calling out something too, but I was concentrating on giving Aunt Janey her orgasm.

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