tagTranssexuals & CrossdressersThat's What Friends Are For Ch. 01

That's What Friends Are For Ch. 01


My best friend was David. David and I had been close friends since we were teenagers in high school and we're still close friends now that we are in our twenties living adult lives in the city.

David always had a certain power over me. "Alex let's go out tonight and pick up some chicks," "Alex it's a beautiful day today, we're going to the beach. Be ready in an hour!" "Aly, you said you were free tonight, we're going to a bar to watch the baseball playoffs. Done!"

David was always on the go, always getting us into new things. He charged ahead and I was happy to follow along for the ride. He was type A and I was type B. David was pretty entertaining.

Over the last few years David had started working out all the time. He always had a lean, toned body from running cross country and swimming on the swimming team in high school, but now after a few years of weight training he had the perfect, muscular in all the right places, jock body. Without a shirt and with his curly, sandy brown hair, he looked like a Greek god.

He had tried taking me with him to the gym but I couldn't keep up and I didn't really like weight training or the gym for that matter. I felt a little insecure there with my tall, petite, slender body, compared to all these jock like guys.

When David and I would walk into a bar ,within two minutes he had us talking to two ladies. He always knew exactly what to say to press a girl's buttons and within 15 minutes he would have a girl making out with him in the corner. I was helpless. David would try to give me hints and tips but I was never able to pick a woman up. David said I needed to act tough and act like a man. Sometimes I would look over at David, his shirt accentuated his fit body, and I would question whether asking out a girl is what I even want. Sometimes I felt like the whole reason I was always going out with David is because I just wanted to spend more time with him.

"Aly, you're too much of a girl."

"Shut up David!" There was a pause. I had blurted it out really loudly, which I immediately knew was a mistake. David loved getting a rise out of people and now he saw calling me a girl had a reaction on me. The thing is, deep down, I wasn't really that offended. I liked when he teased that I was a girl. It was fun and playful. Yet, I felt I still had to keepup a façade and defend whatever remnant of masculinity I have.

Now, ever since I had once blurted out "Shut up David", David always found a way every time we hung out to call me a girl once or twice. "Stop being so indecisive." "Stop being such a girl all the time! "What do you mean you don't know what to wear? Are all your skirts at the dry cleaners?" Dude's put on a shirt and some jeans and go!"

I don't know why, but I kind of liked when David would teasingly call me a girl. It would start to take on a life of its own. He would always insert it now into conversations. Sometimes we would be texting and if I dared say I couldn't go out one night he would say, "what's wrong? Is it that time of the month again? Did you soil all of your panties?" It was always something girly about me that he would say. It was getting more frequent.

Then, we were at a bar talking to two girls a few weeks ago. David recognized the hotter one, Daphne. Apparently they went to college together and had hooked up a few times and she was so happy to see him and started telling us how her and David's college friend Ben is throwing a big Halloween party in a couple weeks and we have to come.

David and Daphne started getting more flirtatious and it clearly looked like he was going to take her home that night. Suddenly she complained "Ugh!!" And started complaining to David how her nail polish was chipping off her nail.

"Oh don't worry, Aly here has a whole collection of nail polish at home, Aly could you lend her a bottle from your collection."

"Uh, you have nail polish?"

"Ha, no. I don't know what David is talking about!" I looked blushed and I kind of liked when he made me blush. In those moments I would look up at him, with his broad shoulders, his strong body and with me feeling a little girly I would feel like I was getting hard in my underwear.

Meanwhile we both looked at David with surprise.

"Oh. I don't know. With Aly, I wouldn't be surprised. He acts like such a girl anyway that I thought it was just natural that he would have some nailpolish"

Then Daphne said "well Aly even if you do wear nailpolish, I think a guy in nailpolish could be hot."

"Guys, I don't wear nail polish."

"Then David of course had to chime in again, "of course not Aly. Not yet..."

I didn't really know what David meant by not yet, but I was turned on by the whole conversation. I excused myself, left the bar and went home.

Over the next 2 weeks David and Daphne hooked up a couple times and then apparently mutually agreed that they're both not each other's type and they're going to stay just friends.

So then a couple days ago I was hanging out at David's. We had a few beers each and were watching TV on his couch and suddenly he comes out of his room holding a plastic bag and says "hey, remember that girl Daphne from Seattle that I fucked the other night?


"Well she left her bra and panties here."

"Ha. That's funny."

David pulled a red satin bra and red lacey panties out of the bag and said, "come here for a sec."

I willingly got up and walked over to him while wondering where's he going with this.

He pressed the bra against my shirt and said "I wonder what you'd look like in her bra and panties.

"David, don't even think about it!" Even though I felt my cock had immediately warmed up and arose to the possibility of putting on a bra and panties.

Aly, you're thin. I think these would fit you!

"David, can't we just watch the game in peace?"

Aly, why can't we watch the game with you dressed in these. Stop whining like a girl all the time, Aly! Just be a sport and do it. It will be funny. We'll laugh. And knowing you, you'll probably like it!"

He pressed the bra and panties against my chest, then slid them down my side, opened up my hand and put them in my hand and said, go change.

It probably took me 5 minutes to take off my shoes and socks, take off my shirt, pull down my jeans and underwear and put on the bra and panties as I kept fumbling around the bathroom while trying to also keep my raging hard on under control. I finally walked out of the bathroom and into the living room and I immediately was blinded from the flash of his iPhone!

"Ha-ha priceless! This is an awesome picture!"

"David, you're an asshole!"

"Look at this look of joy on your face! Ha!"

I was so shocked I was speechless. David immediately came behind me, wrapped his arms around me, cupping his hands around my bra and said, "Aly, baby, you look great! And thanks so much for putting them on for me! You're doing fine. Here's a beer and go sit down.

I was so hard. The sexy, satin bra and panties felt so good on me and I felt so feminine in David's arms. I couldn't remember if he had ever wrapped his arms around me before but this was hot.

Somehow David convinced me to sit down and watch the rest of the game with me sitting in a bra and panties. Every so often David said "Aly nice panties." I blushed. Then I said, "you're enjoying this way too much!"

"Yeah, I am, now take your sucks and stuff your bra. I want to see you with realistic tits!

"Ok, I'll play your game. I was so hard I was almost ready to cum in Daphne's panties. I stuffed my bra and said "what next, David, do you want me to be your cheerleader like the ones on the TV."

He chuckled. Then he said stand up and he came from behind me and put his arms around me, feeling up my stuffed bra. "Ohhh feels nice. I like your tits Aly. It feels so sexy on your girly little frame. I'm going to need to give you a girl's name. I like Allison."

"Oh my god! That's enough! You're not calling me Allison!" I tried to wrestle out of his arms.

"Oh, Aly! Look how hard you are! Something tells me you like the name Allison! Just do what I say and I'll make sure not to ever call you Allison in public. But in private, when you're dressed up as a girl for me, you're Allison."

"David you're crazy!"

"Allison I don't like looking down at your plain toes. Next time we hang out I expect to see them pedicured and painted in a sexy color for me."

"Ok David." I said jokingly. "Whatever you say..."

"Anyway, baby, I think this is the best time for me to tell you that for the couples Halloween party next week at Ben's, I decided we're going to go as Brad Pitt and Angelina Jolie. You, Allison, need to start thinking of what you're going to wear as Angelina!"


Suddenly while in David's arms, he took one hand of his and started feeling my cock. It felt so good.

"There's no but, I can tell from your cock that you love this and I'm going to tell Daphne that she has to do all your makeup. The goal is you're going to be passable!"

I was getting harder.

"Allison, you're going to be all dolled up next week. You're going to be shaved smooth and with your naturally feminine silhouette, and heels, and some sexy lingerie and an amazing dress, and a wig you're going to be hot as hell Allison.

He started stroking me.

David continued, "repeat after me I'm going to be hot as hell."

I complied. "I'm going to be hot as hell." He kept stroking. I was about to blow. I turned to look at him and he had his eyes closed. Then he started to kiss the back of my neck.

And he continued. "Ok Allison. Say: I love the name Allison and am going to try my hardest to act as girly as possible and feminine as possible and wear nail polish, heels, panties, bra, a sexy dress, makeup and a wig so that after the party, my boyfriend David will fuck me."

He kept stroking me and was kissing my neck and started nibbling on my ear lobes. I was ready to explode!

I turned around to kiss him and noticed him, with his eyes closed, and his pants tenting. He was hard thinking about this too!

turned back around, he kept stroking me, and as I felt I was about to cum, I repeated, "I love the name Allison and am going to try my hardest to act as girly as possible and feminine as possible and wear nail polish, heels, panties, bra, a sexy dress, makeup and a wig so that after the party, my boyfriend David will fuck me." He kept stroking me and stroking me.

"That a girl, Allison. I can't wait to fuck you. And I love playing with your little clitty. You have permission to get all wet now.

At that moment I cummed and shot a load into Daphne's panties! It was kind of a humiliating feeling as the panties filled up with my cum but it felt so warm and good and I was still being held by one arm by David. Standing up with him behind me.

I was so excited about Halloween and what's my friendship going to be like with David.

"Allison, one more thing before you change. You should probably buy Daphne another pair of panties."


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