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Jeff Crossdresses More & More

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup.

I never really had a chance to explore it much when I was growing up.

In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I would wait until my roomate wasn't in our dorm room and I'd sneak some on for about 3 seconds. Then I'd freak out that he could walk in and smear it off. By junior year of college I also had a pair of pantyhose and a skirt in my stash. I would wait until my roomate fell asleep and then would put on my skirt which I wore underneath the covers. Its amazing I was never discovered. I don't know how I kept it hidden while sharing a cramped little dorm room. When packing up before summer break I threw out my secret stash and I was devastated about it for months.

After college I got an apartment with a friend of mine, Chris. Chris was an awesome college friend and someone that I felt close with to bounce my ideas off of. No matter what it was I always sought his input. Job plans, vacation plans, anything. When I created a new student newspaper on campus he was the best person to have on my side. He was always helpful with advice and always encouraging me along.

Living together our first few months after college was pretty cool. We were finally both working and making some money. He was very chill to have as a roommate. We never really talked about our days much. We got home. We saw each other. We both scarfed down some food and watched TV. As months went by we started watching TV shows on Netflix. When we finished one season, we would immediately start with the next. After watching all the episodes of '24', we decided to start watching 'Mad Men'. We became obsessed and spent a whole Saturday watching an entire season. It was pretty insane.

All this time, of course I couldn't stop fantasizing about dressing. As the months went by, probably because I saw him so much, Chris started popping up into my fantasies of dressing up as a girl. The fantasy was basically me getting all pretty and then him getting so turned on by a glimpse of me that he would fuck me. Chris had boy-next-door good looks. He was 6"0, brown hair and looked like a taller version of Andrew Garfield from Spiderman.

As time went on my desire to dress kept amplifying. Now that I was working I had saved up cash and really wanted to buy stuff to dress up in.

When it came to talk of Halloween on a Sunday in early October I asked him what he thought of me dressing up as the fiery red head Joan from Mad Men.

He chuckled. "Sure, go ahead. It's definitely gutsy. I have no idea what everyone's going to say but I got your back." Chris was so cool. He didn't seem fazed at all.

Monday night we started watching the first episode of Mad Men's fourth season. Before we started watching, I told him I need to start practicing as Joan as it's going to be really hard to dress up as her.

"Yeah that sounds like a tough costume. Are you sure you don't want to just buy a pre-made fireman costume and call it a day?"

"Nah, when do I ever take the easy way out? I just need to start practicing as her."

Chris looked me up and down in my Brooks Brothers shirt and slacks and Rockport shoes and said "You sure will."

I went into the bathroom and applied some mascara and eyeliner. It was my first time and it was a bit of a mess. My hand wasn't steady enough so somehow I ended up with little mascara marks on my nose and cheek.

Also I put on way too much eyeliner, about half an inch thick, on my lower eyelid so it looked like I was a sad clown.

I walked into the living room. Chris looked up and said, "Yeah, you're going to need a lot of practice!"

I sat there with him watching while wearing the eyeliner and mascara. It felt liberating. He somehow bought this "I need to spend 3 weeks practicing as Joan" story and I can finally wear eye makeup without having to be embarrassed about it or immediately hide it and smear it off. Only when I went to brush my teeth before bed did I remove my eye makeup.

I sat in bed thinking October was going to be an awesome month.

The next night, Tuesday night, I put on my eyeliner and mascara. And the night after I did the same. And the night after I did the same as well. I was marginally improving at putting it on.

It didn't seem like Chris cared. To him I was preparing for my Halloween costume.

Friday was the first time in 5 days we didn't watch TV together. After work I was busy hanging out with some coworkers. We went drinking, and stayed out until 1am. When I got home I went straight to bed.

Saturday morning, I woke up late, was a little hung over and eventually got out of bed and slowly walked into the kitchen to grab some cereal.

"Dude, no eye makeup?"

"What?"

"Sorry I just got so used to seeing you with mascara and eyeliner on. You kind of look weird at this point without it."

"I'm so hung over."

"Since when have you ever used that as an excuse? Eh, I guess you've given up. Well, I don't want to hear you crying when your Joan costume is a fail."

"Chris, You're right! Thanks for the pep talk!" I went into my room, took out my eye makeup and put it on in the bathroom and left the mascara and eyeliner on the counter.

My eye makeup sucked that morning, but I had to capitalize on the chance to wear makeup.

I felt I could start pushing my crossdressing boundaries.

I ordered online some 5 inch heels, a wig and a dress and then went out shopping for makeup.

We agreed to meet back at the apartment at 5pm to catch an episode or two before we each would go our separate ways with Saturday night plans.

On my way home I stopped in Victoria's Secret and was in heaven. Somehow, emboldened by wearing makeup so many times over the past week, I had the guts to walk in there and buy some pairs of panties, bras and other items of lingerie. They had this one irresistible black lace nightie with a little mini skirt at the bottom.

I got back to the apartment. Chris wasn't back yet. I went into the bathroom, cleared the counter of our razors, toothbrushes, his pomade and my dental floss and made room for my foundation, eye shadow, rouge, lipstick, lip liner and lip gloss.

I started experimenting with each item. I had seen enough YouTube videos over the years to have a general sense of how to apply them, but my wrist was shaky out of excitement. Also my cock was so hard.

I looked myself in the mirror. Not bad. My foundation gave me a smooth pale white face. My lips were a tempting red. The makeup all together wasn't so bad, and it suddenly looked unfitting to be wearing my V-neck white men's undershirt and black adidas mesh basketball shorts.

I needed to put on my new Victoria's Secret nightie. I changed and slipped it on and walked into the living room bare foot. I left all my makeup containers spread out on the bathroom counter. I sat down on the couch.

A minute or two later Chris walked in and was surprised to see me all made up.

"Well well, what do we have here."

I got nervous. "Did I go too far?"

"Well I assume not far enough. You're still missing a wig and heels, Joanie."

I laughed. He laughed. I was happy he was taking this all lightly.

"You've definitely stepped it up from just wearing eye makeup. I think you're making progress."

"Me too."

"Cool – lets watch some Mad Men!"

I sat there barely able to contain my glee while watching TV. Joan came on the screen and Chris turned over and said, "Are you taking notes?"

I just chuckled.

The night was fun for me just being able to be outside my bedroom, wearing a full face of makeup and a nightie with a little skirt and not having to worry. Chris somehow was fine with all of this as it was part of my costume prep. I crossed my legs as a woman would.

"Um, one thing. You should think about shaving those legs."

"I was thinking the same thing."

"And Joan wears nail polish." There was a pause. "Just saying."

"I didn't think about it, but you're right." Of course I had thought about it. Just nail polish takes time to put on and off. It does turn me on. I guess I know what to start wearing next.

"And pantyhose! Men LOVE pantyhose!"

For the first time he didn't say Joan wears pantyhose. He said Men! Men love pantyhose. I wonder if he was starting to like me dressed like this. Is he saying he wants to see me in pantyhose? I felt butterflies in my stomach.

That night before bed, as I was washing and wiping the makeup off my face I had to give myself a reality-check. Chris is straight. He is not into me. He is being super cool about me gradually crossdressing more and more. Jeff, don't get delusional and blow this up. He's not going to suddenly want you if he sees your legs in pantyhose!

The next day Sunday was a blur. I went out and bought some nail polish and painted my toenails. I shaved myself completely smooth. I basically spent the day chilling out in my bra, panties and nightie. I couldn't wait for my wig and the rest of my outfit to come!

By Monday there wasn't much going back. I wore panties underneath my work clothes. When I got home, I was surfing the Internet when Chris came home.

"Joanie, I got something for you!"

I walked into the living room and Chris was holding two small packages of black pantyhose.

"I know you're really into this whole prepping to be Joan thing. I thought these would add a little sexy spice."

My brain was saying stop crossdressing for a night, but my cock got hard looking at the picture on the package showing some hot, smooth, pantyhose clad legs.

And how can I resist Chris prodding me to dress?

I couldn't resist the pantyhose or Chris' encouragement.

I went into the bathroom to put them on, and it was my first time in the bathroom all evening. There on the counter all laid out was my makeup collection – the lipstick, the foundation, my makeup brushes, my makeup remover. Everything. All spread out irresistibly waiting for me to put some on.

I put on the pantyhose, put on a little bit of lipstick and walked back into the living room. To top it off I was walking with a swagger.

We sat down and watched some TV.

Finally Chris said, "Joanie, your legs are fucking hot!"

As the week went by – everyday there was something new in the apartment that got me all excited to dress up. One day my wig came, the next day my heels came. Then I got fake eyelashes. Then I needed more pairs of panties from Victoria's Secret. Then I bought a second dress.

Gradually, the apartment was starting to look like a woman lived there. My room had my bright pink Victoria's Secret bags and my lingerie spread across the floor.

By the next Saturday I woke up, hung over again, and looked down at my painted toenails. I had slept in my panties and bra (somehow I gradually had started sleeping in my lingerie) and Friday night for fun I had painted my nails on my hands too. It felt so good.

Chris had been up early. He brought in this charming little flower vase with a rose in it. Then he took down my Pittsburgh Steelers World Champions poster and replaced it with this huge close up shot of Joan from Mad Men. His decorating changes had an effect on me.

I was feeling more and more feminine. I loved it! Every time I went into the bathroom and saw my makeup I couldn't walk out without trying something on!

It was all so fun.

Chris thought the whole thing was hysterical. He started joking how he never thought having a female roommate would be so drama-free. Sometimes he'd grab my ass when I was dressed. It wasn't an overly sexual grab. It was more playful like he just thought this was all funny.

By Monday night I started getting into a rhythm. Home from work at 5:30. Shower, shave smooth and get all dolled up and dressed by 7. Start making dinner.

Suddenly I was also making dinner for Chris too. I was so grateful how cool he was about my month-long crossdressing that I felt it was the least I can do. Plus it made me feel more like Joan.

Chris would walk in around 7:45, plant me a kiss, grab my ass, eat some food. Then we'd watch TV. The costume was all set.

By that Thursday night my makeup was starting to look amazing. I had been doing it now for weeks. Halloween was a week away. We were sitting down to watch the season finale. I was wearing my long red wig, 5-inch heels, red lipstick, pale white skin makeup and some perfume I had bought that day.

Chris suggested for the season finale we turn off the lights. We usually sat apart – I would sit on the sofa and he would sit on the recliner. Tonight he moved right up next to me on the couch and put his arm around me.

During the episode he started to lay his head on my shoulder.

""I love the way you smell Joanie."

And then he started nibbling on my neck. I was so thrilled! I tried staying stoic and unmoved. I was so turned on. He put his hand on my pantyhose clad leg and started to move his hand higher and higher up. He knew how to feel up my calves. He started moaning. I started moaning. He then cupped my bra.

Then suddenly the momentum stopped. He stopped.

"You have got to stuff this bra with something."

I couldn't even move. Here he was feeling me up, like a dream come true and I didn't want to stand up and show my hard on.

While I was still lost in my thoughts thinking about how to stand up to pad my bra, he already had flipped on the lights, run to his room, grabbed some socks and was back opening up 2 buttons from my blouse and stuffing my bra.

"Joanie that's better."

He turned back off the lights and we immediately started making out.

I was in heaven.

He was such a passionate kisser. He held me strongly. He licked my red lips. He bit my lip softly. His tongue kept advancing in my mouth and I just lied there for his taking.

He made me feel so attractive. And so turned on. I tried placing my delicate fingers, with dark crimson painted nails on his cock.

"Not so fast Joanie. You'll have plenty of chances to suck it, but not tonight. I have something better in mind. He smiled.

With all his strength, he lifted me up and flipped me over.

"Is Joanie ready to be taken by a man?"

I was panting. Peaking in sexual excitement and so ready to blow I could barely even talk as I was trying not to just cum everywhere.

"Yes!" I whispered.

"Good girl! I've been waiting for this day. You've been tempting me Joanie for so long!"

He went into his room and came back with a tube of lube and a condom. First he lubed up his finger and started fingering me.

"You like that Joanie?"

"Yes!"

"You want me inside of you?"

"Yes!"

"I want you Joanie."

"I want you too Chris!"

Chris opened up a condom and placed it on his perfect looking 7-inch cut cock and lubed it up.

I got on my knees and he started fucking me. I was trying with every bit of energy to stop myself from cumming but I was so hard and aroused and pre-cumming everywhere. His thrusts made me feel so good inside. I wanted him to keep going, but the thrusts against my prostate were the breaching of my final wall of defense. I erupted all over the sofa cumming and cumming with him thrusting away. And when he saw me cumming he cummed too.

I fell flat on the sofa and he fell flat on top of me.

We lied there for a while in a pit of cum and lube.

He started kissing little kisses on the back of my neck.

He spoke first. "Can you promise me something?"

"Sure."

"Can you promise me that Joanie isn't going to leave us after Halloween?"

"Uh."

"Because I think Joanie is going to be a lot of fun to keep around."

THE END

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