Two Skirts are Better than One

"You know for someone named Harry, you really aren't," I said finishing his left eyebrow.

"I didn't name myself," he pointed out. "But while we are on the subject what do you think of Harmony?"

"I much prefer to sing the melody." I smiled at him to cover my apprehension at not knowing where this conversation might be going. "Then I can improvise more."

"You are so funny," Harry said looking as though he wanted to kiss me but was afraid to move. "I mean, maybe you could call me Harmony."

I had to admit I was taken slightly aback by how fast Harry's transformation was progressing. It would seem that he wasn't kidding when he said he had been thinking about this for a while. I mean two hours ago Harry was my best male friend who knew nothing of my fetish and now he was standing in my bath naked, nearly hairless, asking me to call him Harmony. I kept looking around for hidden cameras.

I thought for a minute, then asked, "What about Harriette?"

Harry stuck out his tongue to show his displeasure at that name. I could not blame him it was a bit antique. "Harmony it is." I plucked one last eyebrow so they were now even and not bushy. "I was thinking of going with Aaron."

"Ha Ha." (Harry will be Harmony from here forward as that is how I came to think of my friend after that moment.) Harmony laughed.

I looked Harmony over and pronounced him done. I spent the next half an hour showing Harmony how to apply makeup. His skin tone and facial lines made it easy. I took him by the hand again and led him to my guest room.

I am not a clothes horse. I am a clothes herd. I have not changed much physically since I turned 18 so I have been collecting women's clothes for almost six years. Having four sisters, two of which are my dress size helps. I have casual and business wear. I also have a huge collection of woman's uniforms, Halloween costumes, and cosplay outfits. I've been a Mystic Clothes and Costumes Premium Member for five years.

I have quite a few pairs of shoes and boots but not nearly as many as I would like. They are so pretty. The problem is that they are also very expensive and my pay grade does not allow for too much variety. Since I do not go outside dressed as a woman, I don't need that many pairs but I still want them.

Now naturally my socks, bras, and panties change all the time. I wear them the most and they seem to wear out the fastest. I wonder if the manufacturers planned it that way. I'm telling you this dear reader as I don't want you to think I am still wearing hole-ridden, stained, six-year-old panties. That would be gross.

I sat Harmony on my guest bed and walked over to the closet and opened the doors wide for Harmony to see my hoard. "What kind of look would you like?" I asked.

"Whatever you think is best," Harmony answered.

I frowned. I got down into his face and repeated the question, "What kind of look would YOU like."

"Skirt and blouse, please," he responded and my heart did a happy dance. Now he was getting into it.

I started to throw things on the bed. I also kept looking back at his dick. I had never had unrestricted access to another guy's goods before and I was taking full advantage of the view. I honestly could not believe how turned on it was to have Harmony here. Maybe it was the clothes. Maybe I was looking forward to binge-watching Star Blazer. I was about to tell myself to stop being such a male pig when I noticed that he was looking at my ass every chance he got.

I pulled out a burgundy blouse, a grey skirt, and a matching black panty and bra set. I had burgundy thigh highs that went with the blouse. I figured that since we were staying in, we didn't need shoes but I had a lovely set of black slippers that looked like Mary Janes that would go with the outfit if he wanted to try them on later. Harmony was a virgin crossdresser so I pulled out my 32A bra inserts and put them in the bra for him.

I got behind him and lowered the bra into place in front of him. Then I hooked it for him. I handed him the panties and he put them on. He closed his eyes and looked as though he had just taken a bite out of a very yummy chocolate bar. "Oh, those feel so nice," Harmony thought out loud as he sat back down on the bed in front of me

I decided to take a chance. I put my arms around his chest under his arms and cupped his bra. I pressed my chest against his back and put my right ear against his head. "How do these feel?" I asked.

He didn't respond for a while. I just held onto him not knowing what to do. He felt so good against me. I thought maybe I had gone too far. Finally, I let go of his bra and started to lower my hands. Harmony grabbed my hands and moved them back to his bra. "The lingerie feels good. YOU, feel great," Harmony said as he leaned back putting more of his weight on me.

"Have you always liked guys?" I asked.

"No," he forced my hands to squeeze the breast inserts again. "When I was ten, I had a crush on my babysitter. Her name was Amy."

"Really?" I asked not sure if he was making fun of me or not.

"Oh yes. I proposed to her like every day." Harmony moved one of my hands to his naked mid-drift.

"You said you liked crossdressers." I had to know, "have you dated other crossdressers?"

Harmony was motionless for a long time. "Dated no. But remember how I told you I had to live in the dorms my first year of school before moving back home?"

"Yes," I answered moving my other hand to his stomach just above the waistband of the panties.

"My roommate, Ethan, was a closet crossdresser. We became friends and then a little more than friends," Harmony admitted a little dreamy-eyed.

"Oh," I said my nervousness showing in my voice.

Harmony brought my left hand up and kissed it, "No need to worry, Aaron. That was three years

ago. Last I heard he had hooked up with some rich guy. Besides he was not half as cute as you."

I kissed Harmony upside down on the forehead. "That's the kind of thing a guy loves to hear."

Fortune favors the bold, kept going through my mind and so I decided to be bold. I couldn't tell you how many times I had sat here just like Harmony was now, rubbing my cock through a nice pair of panties. I reached down and started to rub Harmony's cock. Harmony offered no resistance and so after about a minute I asked, "How does that feel?"

Harmony grabbed my hand stopping me. Crap, crap, crap, I thought. I knew I had moved too fast. What had I been thinking? Then he lifted the waistband of the panties and moved my hand inside so that I was holding his dick. He let go of my hand and I started to stroke his cock. "That'll feel better," he said by way of answer.

Since removing all of Harmony's hair I had been sneaking glances at his cock every chance I got. It was not very big. I mean I don't have many examples to compare it with, other than the ones in porn movies but it looked small to me. I had been very worried about this as I was hoping the sight of me would cause his little man to stand at attention.

Seeing him naked and knowing that he was sneaking peeks at my ass was making me harder than I had ever been. If I am being honest, I am not that big either but I was at least half again as big as him. Now that I had Harmony's dick in my hand, I discovered that while his cock was not that big it was quite hard. I reached up under his bra and started to pinch his nipple. Harmony moaned under my attention.

While I loved making Harmony feel good it was starting to hurt my back. I moved off the bed and onto the floor beside the bed. Harmony fell backward into the bed with a thud. "Hey, I was enjoying that," Harmony whined.

I crawled around to the end of the bed like a house cat. Once I reached the end of the bed, I got back up on my knees in front of Harmony and between his legs. "I am pretty sure that you will like this better," I remarked with a mischievous smile.

I grabbed the set of burgundy stockings that I had set out. I rolled one up and tapped Harmony's left leg. He presented the appendage and I began to unroll the stocking up his leg. He was sucking in air the entire time I was rolling it up his leg and then let out a hhhhhaauu sound as I reached his thigh. I let go of the elastic which resulted in a very satisfying, swack. Harmony fidgeted in pleasure. I repeated the process on his right leg with the same response.

Harmony looked down at me with a big grin on his face. I gave him an I told you so look. Then I snaked my hand in through the right leg of the panties and took his cock in hand. Harmony half closed his eyes and then looked up. I assume this meant that he was enjoying what I was doing to his little man since if he was that interested in my plain popcorn ceiling, it would be a serious cause for concern.

"Oh, Aaron," he moaned, "you are a natural at this."

"I spend enough time playing with my own," I said sarcastically, "I should know how to take care of yours."

"Never trust a thin chef, a sick doctor, or a bald barber," Harmony said to the room at large.

I looked at him a little perplexed. Then I asked him, "Who said that?"

"I did. Just now." He leaned in and kissed me, "Weren't you listening?"

I withdrew my right hand from his knickers and then put both hands on the waistband of his panties. They were all that stood between me and Harmony's cock and they had to go. Now! I pulled down and he must have figured out what I was wanting to do as he lifted his bum to enable me to remove the obstacle to my lust. The truth was these were one of my favorite pairs of underwear but such was my mental state that I had already decided no sacrifice was too great. If they did not come off easily, I would rip them off.

Now face to face with his cock I had to pause. I had spent so much brainpower trying to figure out exactly how to get here, and now that I had the prize, I was not entirely sure what to do with it. I was the dog that had caught the car. I had never sucked a cock before. I mean sure, I had seen it done a thousand times in porn but I had also watched every episode of The Big Bang Theory that didn't make me a physicist.

Harmony must have known what I was thinking or he could read minds, which I've got to say would be super cool, because he whispered, "You don't have to."

"I know," I took a deep breath to strengthen my resolve and I leaned in and kissed the head of his dick. Next, I kissed the left side of his dick, then the right. I didn't have a plan; I was totally winging this. I took his small shaft between my thumb and started to slide the skin of his shaft up and down. Because his cock was so erect there was not a whole lot of give so I only did that once or twice before I switched back to kissing his shaft.

I know it sounds cliche but I licked his pole once on the left and then twice on the right. I looked up to see what kind of effect my actions had had on Harmony. Not that big of an impact as it turned out. In my head, I told myself, just go for it. He's not that big.

I opened my mouth and just as I suspected his cock fit with room to spare. I slowly wrapped my lips around his cock and started to push up with my tongue. I had no idea what I was doing but this time when I turned my eyes upward in an attempt to see how well I was doing. Harmony's eyes were completely closed and the expression on his face was quite promising.

I slowly pulled back on his pole. I was trying to figure out how to keep my lips tightly wrapped around his shaft without hitting it against my teeth. This was for two reasons. First, I was pretty sure that having his dick pulled across my lower teeth would not be a pleasant experience for Harmony, and second, if I screwed up the orthodontia my parents had paid thousands for, according to them, I was dead.

My first half dozen pulls were clumsy, to say the least. I lost the seal several times and had to start over. This was harder than it looked. Then I got into a rhythm and reminded myself this was only my first time and that I was pretty sure Harmony, not only would have tips for me but also would be more than open to letting me practice on him in the future.

In the meantime, Harmony decided that a demonstration was the best way to instruct me on the finer arts of cock sucking. He rose, took both my hands, and pulled me to my feet. We dosey doed, I think that is what they call it, and he went down on his knees. He pulled my panties down and then pushed me just enough so that I landed on the bed with a little bit of a bounce like a newly felled tree. This was so much fun.

I spread my leg and Harmony moved into position. He rubbed his left cheek against my right leg then rubbed his right cheek against my left leg. I was so hot. He repeated this process from just above my knee all the way up to my naked thighs. My legs began to tingle as he moved up and when his bare cheek brushed my naked thigh the jolt was like that of licking the top of a nine-volt battery.

"Fuck!" I said to the room at large.

"Glad you like that," Harmony cooed, "because I love doing it."

As I said before while watching porn and thinking about girls' clothes, my dick usually gets pretty hard. I have never measured my dick when it was at full mast but I think it's about average. At the moment however, after round two of the Harmony treatment I happened to look down and to my surprise, it was quite a bit bigger. "Looks like somebodies happy. Do you have any lube baby?"

Still, in shock over the fact that my cock seemed to have grown overnight, I didn't answer Harmony right away. Undeterred, he got my attention by kissing my inner thigh and leaving a hickey. This resulted in a pleasure pain cocktail that brought me back from my ruminations over the size of my cock and I focused on Harmony, "Huh?" I asked.

"Lube, babe?" he asked again.

My brain was not firing on all neurons yet but I knew the answer to that question. "Top drawer of the wardrobe." Harmony got up and started over to the wardrobe, "Vanilla is my favorite." I said to his back.

He turned and looked over his shoulder, "ooh. Mine too."

I had been looking at Harmony's cock for over an hour. Now I got a very nice look at his ass. It swayed back and forth as he walked. I had seen that kind of walk before, in movies and on a fashion show runway videos online. His hips were mesmerizing so much so that I was almost sorry when he found what he was looking for and came back.

"What's wrong?" Harmony asked.

I smiled sheepishly, "Would you mind walking back to the wardrobe for me?"

"Sure," Harmony responded.

Halfway across the room, he must have figured out what was going on and so instead of walking back in the normal fashion, he came back to the bed backward so I could look at his butt the whole way. I playfully patted him on the backside and he got back down on his knees setting the bottle of lube on the bed. "So, you're into ass, huh?" he joked.

"Mainly yours." I admitted tilting down so we were virtually noise to noise, "It's so pretty. I can't wait to get you into some short shorts or yoga pants and just watch you walk around the room."

"OK." Harmony smiled, "Since this is your apartment, I will give you the choice. Do you want to watch my ass or do you want to stick your dick in it?"

I was focused now. The thought of putting my tab "D" into Harmony's slot "A" filled me with both exhilaration and trepidation. I had never done that before. Seen it done a bunch of times online but never actually done it myself. I licked my lips. This was going to be a day of many firsts for me.

I moved to get up but Harmony pushed me back down. I tried again and he pushed me back down. "I thought you wanted me to fuck your pretty little ass?" I asked.

"I do," he assured me, "but first I have to get you ready."

Harmony sprinkled some lube onto his hand and started to stroke my cock. He then took my balls in his left hand and cradling them gently he began to kiss them. I made a mental note to do the same the next time I was between his legs. He then moved on to kissing the base of my shaft until he was all the way to the tip. Then he looked up at me, opened his mouth wide, and swallowed my whole dick.

It was very obvious that unlike me, Harmony had done this before. I could not wait for Harmony to teach me everything he knew. I could not help but wonder how many times he had done this to Ethan. I was trying not to be jealous. I was failing miserably.

I was brought out of my thoughts by Harmony letting go of my dick and moving his now free hand down to my crack. He traced my crack with his forefinger a couple of times. Then he did it again with two fingers and along the way, he would stop and massage a spot here and there in my crack.

My hands moved of their own free will. I started to run my fingers through his hair. Then they grabbed the back of his head and started to pull his head closer to my crotch so that he had to take me deeper into his mouth.

Harmony let go of my balls and I presume he started playing with his own. He then also pulled back enough that he was able to disgorge my cock from his mouth and began to kiss my balls again. He then headed south kissing me under my balls. Then he found my rosebud and started to play with it using his tongue.

I lurched up. Harmony must have been expecting this response and so had his arms ready to wrap around my legs when I tried to get away. He kept licking. The feeling was different, that was for sure but also very pleasant. Still, I had to stop him or I was going to be lost in the pleasure of it.

"Harmony," I tapped him on the head but he didn't stop.

"Harmony? I don't see how that will help me." He still didn't stop.

"Hey," my voice was finally forceful enough to get through to him.

He pulled back breathing hard. "Sorry. I lost myself there, for a minute," he explained.

"So, you're an ass man too." I joked.

He laughed and I helped him up. Harmony laid back down on the bed face up. I picked up the bottle of lube and poured some on my cock. It was cold. "No, No, No. Warm it up in your hands first." Harmony coached me after the fact.

I kind of already knew that from experience but figured the cold lube would help to slow my engine down enough that I didn't blow my load right after I entered his arse. "OK, now put some lube on your hand and then rub your hands together," Harmony instructed.

I followed his directions.

Harmony pulled his legs up exposing his arse to me. "Now slowly insert your forefinger into my ass."

I followed his direction.

"A little slower please," he directed, "I haven't done this for a while."

I slowed up but before too long my finger was in up to my knuckle.

"OK," Harmony sighed, "now pull your finger out, lube up two fingers, and put both of them in me."

I did as he asked. The fingers went in way faster this time.

"That's great." he commented, "Now in and out a couple of times."

"Am I doing this right?" I asked really nervous.

"You couldn't be doing it any righter baby." He said and closed his eyes again. "Danm that's fucking good."

I simply sat there putting my fingers in and out of him. I was amazed by this little tug-of-war I was having. I pushed in and his sphincter pushed me out. It was like a game of I don't want it you take it.

"Having fun?" Harmony asked.

"Yes."

"You want to put some lube on your dick and try that?" Harmony inquired, "It will be more fun for me and way more fun for you."

My nervousness returned tenfold. But I knew I needed to face this Jabberwocky. I took the bottle of lube as poured some on my vorpal sword and walked over to Harmony. "You got this Wild-star," Harmony said encouraging me.

Way slower than I had with my fingers I slowly put the head of my dick into Harmony. Suddenly he let out a terrible grunt. I jumped back asking "What, what. Are you OK?"