That's What Friends Are For Ch. 02

I woke up in the morning both loving and hating what had taken place the previous night when my best friend David made me dress up in panties and a bra for him and promise that I will dress up as a girl for him on Halloween.

All I wanted to do was please him. He wanted to see nail polish on my toes, so that's what I was going to have to do. I happened to have one bottle of nail polish in my apartment so I went into my bathroom wearing nothing but Daphne's bra and panties, sat down on my rug and began to paint. I was going to be late to work because of this, but it needed to be done.

...

That day at work, I tried not to seem distracted, but I kept thinking about how hot it was for David to command me to dress up as a girl for him. Deep down I had loved every second of it. And now I loved that I was wearing nail polish on my toes for him.

As if I was not distracted enough, I felt the vibration of my cell phone and when I looked at the text it was from David, "hey slut."

God I loved that he just spontaneously texted me and called me slut. I was immediately stiff as a rock and replied back, "hey."

He replied "glad to see you're answering to that nickname now, Allison."

I was embarrassed to see him texting the name Allison during the day at work. What if I had left my cell phone on my desk and my co-workers would accidentally see? That would be so embarrassing!

"David, maybe you shouldn't call me Allison during the day?"

"Why not?"

"Come on, David. I'm at work."

"Are you wearing your panties underneath your clothes right now?"

"No, I'm not wearing panties at work."

"Well, I'll let it slide this time Allison, but next time I ask I expect to receive a picture message back from you of your panties underneath your work clothes."

I looked around and it seemed everyone around at the office was minding their own business and weren't alert enough to notice I was aroused.

David continued, "So Allison leave your office by 5:30pm tonight. You have a busy night ahead of you."

I was hoping to watch some Thursday night TV, but David had other plans. "What's on the agenda?"

"We have to get you purrrty. It's already Thursday and we have to get you up to speed to be my sexy little bitch by the party on Saturday. I've enlisted Daphne to help on this and I'm sure you'll have fun talking about whatever girly things you two talk about."

The text from Daphne came about fifteen minutes later.

"Aly, umm, David says you have my bra and panties?"

"Ha, yeah." I didn't even know what to say. Little does she know I've already cummed in those panties twice. Once last night with David and then once by myself this morning before leaving for work.

"Apparently, you've been wearing them?"
"I was just trying them on for my Halloween costume."
"Yeah, David says you were begging him that you wanted to dress up as Angelina Jolie so he's going as Brad Pitt to be a good sport. I love David. Just when you think he's a total douchebag, he shows he has a heart."

David is such an ass. Did he really need to tell Daphne that I was wearing her bra and panties? I hope he's not going to start telling people about my dressing. Who knows what he has up his sleeve.

"Okay Aly here's the deal I'm basically completely busy this week until the Halloween party, but I do want to help you, as you definitely need a lot of practice if you want to be Angelina Jolie! I had plans to hang out tonight with my friend Ben, who's throwing the big Halloween party on Saturday, but I'm changing my plans so that we can do your makeup tonight.

I figured I would take what I could get, "Great!"

"Aly, here is your shopping list: Buy: your own heels, dress, wig, bra, panties, pantyhose, fake boobs, nail polish, foundation, rouge, eye liner, mascara, eye shadow, lip liner and lipstick. Oh and you're going to need to shave your entire body completely smooth. Don't worry about being embarrassed in stores today, no one in retail is surprised when a guy walks in before Halloween looking for assistance in dressing up in drag. We're going to make you look hot! See you outside your building at 5:30!

The rest of the day moved painfully slow. I couldn't concentrate for a minute at work.

At 5:30, I walked outside and saw Daphne holding a large shopping bag.

"Hey sweetie, I found a store in town that caters to crossdressers. From there I was able to get you heels, a wig, a dress, and some silicone breast enhancers. You're going to look terrific! Our first stop Aly is Victoria's Secret.

We walked into the store. I was so turned on by the sight of all the satin and lace and all the sexy little outfits on the manikins. All of the lingerie was so sexy.

Daphne immediately walked up to a saleswoman, "Hi my friend here Alex is dying to dress up as a girl and I was wondering if you could fit him for a bra. Then if we can maybe find some sexy lingerie for him and a corset to give him a nice feminine shape."

I blurted out "...its for Halloween!"

The saleswoman did not flinch. "Right." Then she looked me in the eye, "Halloween, not for Halloween. I don't judge." Then she winked. Daphne meanwhile smiled from ear to ear. I can only imagine what David had told her.

The saleswoman took a measuring tape and wrapped it around my chest. It was hot. She showed me a push up bra that really added some cleavage. Ten minutes later we were out of there with a new set of bra and panties for me and a new set of bra and panties for Daphne, which I bought her since I knew she was never getting back the pair that I now had in my possession at home. I also saw some sexy pieces of lingerie and couldn't help myself from buying a couple of nighties. I told Daphne that everyone knows Angelina Jolie wears sexy lingerie so I needed to have some. Meanwhile I was thinking it would be something sexy to wear and pleasing to wear over my bra and panties in case David would be sleeping at my apartment.

The hardest part for me was going into Rite Aid and mustering up the courage to stand in their cosmetics aisle and buy everything we needed plus some fake nails, fake eyelashes and some pantyhose. Luckily I had Daphne with me.

When I got home with Daphne she immediately had me come with her to the bathroom. She commanded me to strip and I stripped. Within seconds I was standing next to her completely naked.

"Pretty nails!"

With all the errands I ran all day I had completely forgotten about my early morning pedicure.

"Do you always paint your toes? I remember David saying something how you have a whole nail polish collection."

I wanted to correct her, but I also started liking to live up to all the girl innuendo that David would say about me.

"Aly you need shave your body!"
"I know, but it's not Halloween yet. Do I really have to?" I was suddenly worried about losing one of the last remnants of my masculinity.
"Excuse me this is your only dress rehearsal! We need to test if you are going to look like a chick for the party. Otherwise I'm sure David will find another chick to take as his date in 10 minutes!"

She was right. She filled the bathtub with warm water.

"Here's a razor, Aly." She handed me a razor and some shaving cream. She left the room and I realized I had to proceed. If I want to dress up for David I have to go through with this and I started to shave. She came in fifteen minutes later and saw I was all smooth.

"Ok, manicure time!"
"Daphne, I really don't think it's worth our time to give me a manicure. Let's proceed to the actual makeup."
"Aly, or shall I say Allison, do you really want to be David's girlfriend? It's time you listen to my pointers. A pretty manicure will get you in the mood. It's a fun, girly reminder every time you look down at your hands."
"Who told you to call me Allison?"
"Who do you think?"

She showed me her iPhone and there was her text conversation with David.

Daphne had texted: "Guess who's over my house right now?"
"Surprise me."
"Aly! And I caught a glimpse of his pedicured toes. I think you were right about him having a whole stash of nail polish."
"Ha, I knew it! Let's start calling him Allison"
"haha"
"It will get him in the mood for Halloween."
"Ok!"

I put on my purple, shiny satin bra and panties from Victoria's Secret, and she put in the breast enhancers. The cold silicon came as a refreshing sensation to my warm skin. I looked down at my filled bra and it looked incredible. I knew David would love my rack.

Daphne then proceeded to paint my nails a deep red nail lacquer from OPI.

Then she went about opening up the glass jar of Revlon foundation, took out a long slender brush, lowered the brush into the jar and then started applying it to my face. The cold sensation of the liquid makeup on my face was exhilarating.

She then opened up a little box containing fake eyelashes, took out and squeezed some glue on each one of them and then applied them to the edge of my eyelids. My long fake eyelashes were now glued on. She then proceeded with eyeliner to outline my eyes and then brushed mascara through my eyelashes. Finally she laid on a thick layer of blue eye shadow. She opened up a tube of lipstick and carefully smeared the red lipstick across my lips. Then she moved to her rouge and applied the rouge brush with pinkish rouge just under my cheekbones. I tried taking it all in. I was loving every moment of the transformation.

We then put on my black sheer pantyhose, my sexy little black dress and my 4 inch black patent leather heels and finally my shiny blonde wig. I looked hot. I took a picture on my phone and sent it to David.

Meanwhile Daphne gave me a whole tutorial on walking in heels and we were having so much fun.

"Allison I'm helping you out for selfish reasons."
"What do you mean?"
"Well I've been meeting a lot of guys since I moved to the city, but I don't really have many girl friends. I need someone like my sorority sisters in college that I could talk to about guys, get mani/pedis with, read US Weekly and talk fashion, go shopping together and laugh and cuddle with."
"I'd love that!"
"I already knew you would! You're just so naturally effeminate that you never seemed to be digging all those guy activities with David. Besides you're so pretty as a girl that it would be criminal to have you waste away as a guy."

The doorbell rang. There was no way it could be David just sixty seconds after I texted him.

"Daphne are you expecting visitors?
"Ya I told my friend Ben to come by for some wine."
"But I thought you cancelled on him!"
"Listen Allison; I wanted to have him come by as a test to see how passable you are. He's never met you as Alex, so let's see if he finds you hot as Allison.

I was getting hard in my panties as Daphne went to open the door.

There was Ben. Boy next door looks. Dark brown-gelled hair, brushed to the side, pale white skin, piercing blue eyes and wearing a t-shirt and jeans.

Suddenly my heart was fluttering. Do I wait sitting or do I stand up and approach him.

He proceeded to walk over, then confidently and loudly asked "my my Daphne you didn't mention you had any friends over!" He looked into my eyes, stuck out his hand, "Hi what's your name I'm Ben."

In my girliest voice, "I'm Allison." I rested my delicate hand in his large warm palm.

"Well Allison it's great to meet you. I hope you're going to stay for a glass of wine with us." While holding my hand he lead me over to the couch and started chit chatting with me about wines and how he loved pinot noir.

I felt so sexy sitting there and seeing his eyes every so often drift to my legs and my tits. I was taking it all in. Between keeping good posture, smiling at him and batting my eyelashes, I didn't have a second to remember that I was Alex. It was all about looking hot as Allison.

Ben took a wine opener and opened up a bottle of wine. There was something very romantic and tantalizing about him.

As he poured me a glass he kept looking into my eyes and smiling and kept eye contact as we clicked glasses and both drank.

He started telling stories about when he spent the previous summer working on his uncle's vineyard in Napa Valley and he kept making me laugh.

"Allison I'm throwing a big Halloween costume party on Saturday night and I would love it if you could come as my date."

"Well..." it was Daphne. I had completely forgotten she even existed over the 15 minutes that I sat with Ben on the couch.

"You see Allison is already going to your party as David's date." Daphne had this mischievous look in her eye as if she knew she was opening a can of worms.

"David? Allison how do you even know that idiot douchebag? Are you guys dating him?"
"No."
"Fine. So then he'll have no problems letting you come as my date. I'm having 75 people over, I was kind enough to invite him to the party and I want you Allison to be flanked at my side the entire night looking as hot as you do right now. We'll just give you a little leopard tail and a leopard headband with 2 tiny ears and you can be a feline seductress." Ben had used his pitch as a subtle distraction to distract me from the fact that his warm palm was now on my pantyhose-clad thigh and he was slowly starting to rub his hand further up.

"I think I need more wine," I tried to distract him. I loved this whole scene of being dressed up and felt up by Ben but I also felt guilty knowing I'm doing this all for David and now some other guy is moving in on me.

Then again, David is a douchebag and Ben is a gentleman.

Ben handed me back my glass, and clicked his glass with mine, "here's to my first upcoming date with you Allison."

"Here's to our first date together Ben."

Daphne walked into the other room and with the coast clear, Ben moved in for the kiss. The next thing I knew his tongue was entering my mouth like a freight train while his hand kept stroking my thigh and his other hand had cupped my butt. I felt so sexy and was hoping that he couldn't see my hard on since it was buried under my restricting pantyhose.

His masculine scent, his defined jaw bone and his hot forcible tongue made me unable to resist his advances. We were heavily making out while he was feeling me up.
As he crawled over me he said, "I bet you give good head!"

"I do!" I don't know what possessed me to say that, since I never had cock in my mouth before but I said it.

Good! He unzipped his fly and pulled down his jeans. I got on my hands and knees on the floor in front of him and without any force "Come on sweet Allison let me see my cock in your mouth," I began to put his dick in my mouth. It was 6 and a half inches. Not too big but enough for me to almost gag on. I had never had cock in my mouth before but it was amazing. It had the size and breadth of a massive knockwurst and was hard as a lead pipe. I kept blowing back and forth and suddenly I felt him stick his finger into the back of my pantyhose and he moved his finger further and further down until he got to my butt and started to play with my boipussy. I started to moan. He pushed further. And I kept blowing faster and more enthusiastically while looking up at his beautiful blue eyes.

"Allison you're such a hot chick, keep taking my cock Allison, fuck yeah!"

"You're doing great, Beautiful. Just a little more, a little more Allison! Wow you're so hot, I can't wait to make sweet love to you!"

His finger was now in my boipussy and matching the rhythms of my blowing him with pressing his finger further into me.

"Yeahhh! Just a little more, now Allison. Keep up that pretty little blowing of yours, yeahhhh!!! He started cumming in my mouth and with his finger so far inside of me I started cumming too.

I don't think he noticed my cumming as my cock was so hidden behind panties, 2 layers of pantyhose and my dress.

"Oh Allison that was amazing. I can't wait until Saturday night and we can make love again. You're beautiful Allison, have a good night!

He zipped up his pants, got up and let himself out.

I was left in the living room, cum in my mouth, cum in my panties and left with serious boy trouble. I have dates with 2 guys to the same party on Saturday night. I preferred Ben, but who knows what David would do to me if I stood him up...

TO BE CONTINUED