With a Friend's Help Pt. 01

It was early in the evening and I was sitting watching something on Netflix when the doorbell rang. "Who could that be," I said to myself. I jumped up and made sure I was decent, rearranging my tracksuit bottoms and t-shirt, and went and opened the door.

"Hey gorgeous," Jess said from the doorstep. I smiled. A visit from my best friend was always welcome.

"Hey you," I replied. "To what do I owe this pleasure?" I stood aside and she entered, looking as stunning as always. Her firm bum squeezed into her tight blue jeans, a purple vest top.

"Thought I would come and see my favourite person," she said, looking back over her shoulder. "You checking out my ass, or my new jeans."

"Both," I said. "Hard not to look." She had such a great body. Tall and slim, her long dark hair flowed silkily down her back.

Jessica was my best friend, no more, no less. A year younger than me. There had been some drunken kisses over the years, which we laughed about, but I wasn't her type, and I still wasn't sure what my type was.

Jess liked masculine men, or hot women, she couldn't make her mind up. She liked the freedom of being single and playing the field, as they say.

I was slightly more complicated. It had taken years to work out what I wanted, lots of trial and error, but I believe I was starting to work it out.

"What did you get up to last night then?" I asked. We had been out and Jess had ended up with some fine looking stud. She had asked my permission first if she could slip away, we would never leave each other without asking. We were out with others so I obviously said yes, as long as she gave me the gory details.

"Or should I say, what got up you last night?" I added.

"I don't think you should ever say that!" Jess laughed. "It wasn't bad. He had a pretty amazing bod, and not a bad cock, but he didn't blow my socks off, so to speak."

I shook my head. "You're just too fussy," I said. "I wouldn't have been complaining." I was jealous. It wasn't that I wanted the guy she had been with, I was jealous because I wanted to have been Jessica. I wanted to be the sexy confident woman getting fucked by the hot guy.

This realisation had been what had taken me so long to come to terms with. I had known I was different at a young age, I had alway been pretty feminine. I had grown up liking girls though, finding them very attractive. I had gone through a few relationships with women, but nothing serious.

The porn I had preferred was standard, man on woman, or lesbian. I occasionally started to dabble in gay porn, but it didn't hold my attention as much as straight porn. The more porn I watched though, the more the realisation hit me. I wasn't watching it wanting to be the man fucking the woman, I was watching it for the fantasy of being the woman getting fucked.

I wanted to be taken like Jess, I wanted a cock inside me as a female. Mouth, or ass, either would do. These days I got off on transexual, or transgender stuff as well.

It wasn't long ago I shared this with Jess. I had felt sick as I spoke to her, I had been so anxious. I was worried she would think of me as a freak. I knew she would never say it, but what if deep down that was how she thought.

I needn't have been worried though. To say she had been excited would be an understatement. She had hugged me, and had been proud that I had finally discovered who I was, and could tell her. She had dragged me straight off to the bedroom to dress me up. Millie was born.

"What food have you got?" Jess said, dragging me out of my day dream. She started raiding my fridge as always.

"I'm sure you'll find something," I replied.

"How's Marcus?" she said. I laughed. Marcus was the nickname we had given my 10 inch rubber cock that Jess had given me for my 21st.

"He's good thanks," I said. "Been busy."

"I bet he has," Jess said. There was a twinkling in her eye, a big smile on her face. She changed the subject though so I didn't get the chance to find out why.

"You know how you're my bestest, most gorgeous baby?" she said.

"Here we go," I mumbled.

"Don't be like that," she said. "It's only a teeny favour. One that I'm sure you'd love to do to help out you're longest, closest, clothes lending sexy honey."

"Yeah. Yeah. Get on with it Jess," I said. This was a lot of creeping even for her.

"Okay," she said. "I want you to come on the hen do with me?" I looked at her like I didn't get the joke, but she just looked serious.

"I can't go on a hen do Jess," I said, laughing. "I don't know if you noticed, but I'm a man."

"Hardly," Jess said. Laughing.

"Oh you bitch," I said, laughing too. The hen do she was on about was Laura's, her brother's girlfriend. I know Jess had been anxious about it, she didn't know anyone there. She had only met Laura a few times and even though they were friendly with each other, they hadn't really got on overly well. Jessica's description of her was 'a stuck up cow.'

Jess stopped laughing and looked serious, almost embarrassed. "I didn't mean as you," she said quietly. I stopped laughing, looking at her quizzically.

"What do you mean?" I asked. I suddenly knew where this was going.

"I want you to come with me as Millie," she said. I looked at her for a while, studying her pretty face, staring into her deep green eyes.

"You're being serious?" I said.

"Please!" Jessica pleaded.

"No way Jess," I said. "I'll never pull it off for a whole night." It was tempting though. I felt the thrill just thinking about it. How amazing it had felt last time.

"You looked amazing though," she said. "Honestly no one will work it out. I need you there. I'll help you get dressed, I have some clothes you'll look amazing in. I can't go by myself, I don't really know anyone. Please Tim?"

I thought about the amazing clothes Jess had, how I envied the choice of clothes she got to wear, how sexy they looked. I thought back to last weekend, Jess dressing me up, and how it felt to wear what I did, how great I felt in them.

"I'll think about it," I said quietly. Jess squealed and jumped up to hug me. "I said I'll think about it" She squeezed me so tight I couldn't breathe for a second.

"You won't regret it," she whispered into my ear. She kissed me on the cheek.

"I'll hold you to that," I said. I couldn't lie to myself, I was excited. The thought of seeing other people's reactions was both scary and arousing. She pulled back from me, holding my arms still.

"Thank you," she said, smiling. "We'll make a day of it. You can come over early and get ready. I've already got an outfit planned for you."

"Hope it's decent?" I said.

"You mean you hope it's not," she replied, laughing. She saw my face. "Don't panic, it'll be perfect.

We talked about the hen do. Her brother lived further up the country. That was where we would have to go. It turned out Jess had already booked a twin room for us, knowing I would say yes, to my annoyance.

We talked logistics. Me going around early and getting ready, train up there, stay over, and train back the next day. I started to warm up to the idea, starting to get excited.

What would it feel like to be out as Millie. Would people know I was male, or would I get admiring glances. I refused to get excited too much, else I might be disappointed.

"Why aren't you in any of the outfits we got you?" Jess suddenly said, bursting my train of thought.

"I didn't finish work till late," I said. "Haven't had time. I've got on a few bits." I mumbled the last bit.

"What bits?" said Jess. Perking up. She leant forward on the table.

"I've got those thigh high stockings on, and pink silk panties, under here," I said, my eyes flicking to my lap.

"Mmmm," Jess softly moaned. "Sounds sexy. Bring those with you to mine. Maybe they'll go well with the outfit."

"Can't wait," I said, it burst from my mouth.

"Neither can I," said Jess. "You're going to look hot. There'll be plenty of men after your tight little asshole." She winked.

"Jesus Jess," I said, laughing. She had a habit of saying whatever she wanted.

"What!" she said, innocently. "I better get going." She stood up. "Say hi to Marcus for me." We both laughed.

"Say hi to your disappointing shag for me," I replied. We walked to the front door, Jess opening it.

"He's long gone," Jess said. "You know I don't like them hanging around."

"Words of a true slut," I joked. We laughed and she hit me on the arm. She leant in close.

"You'll be the slut after this hen do," Jess said. I felt the breath on my ear. I gasped and felt my cock stir. Before I could say a word, she kissed me on the cheek and left.

I stood there for a minute, wishing her words came true. It felt like teasing, but I sensed something else in her actions, but I couldn't work out what. It was probably just Jess being Jess. I was horny now though. The thought of truly being Millie was too much.

...

When Jess left I pretty much ran upstairs. I couldn't get the thought of taking the next step as Millie out of my head. The thought of being seen out and about as a girl had me excited. I knew I was being silly, and hopeful, but I thought about pulling a fit looking man and what he would do to me.

I stood in front of the mirror and took my t-shirt off and then dropped my tracksuit bottoms. I ran my hand over the stockings I was wearing, and then felt my hardening cock in my pink silk panties. The outline stood out against the fabric and grew as it stiffened to its full 6 inches, straining against the fabric. I ran my hands over my skinny body, my narrow hips, and my toned stomach, and thin waist. My chest was disappointingly flat, maybe one day, I thought. My body was completely hairless, it was tiresome shaving, but it was worth every second.

I reached up and took the hairband out of my ponytail, letting my brown hair fall down over my shoulders. I brushed one side behind my ear. I loved my hair. The one thing that was part of me that I could let become feminine naturally. That and my pert bottom, that had taken more effort though.

I turned sideways in the mirror and squeezed my bum cheeks, letting my fingers slide between them, teasing myself through my panties and pushing the fabric into me. I moaned softly. I couldn't wait now and dropped my panties to the floor, I stepped out of them.

I squatted down, my cock straight out and hard, and picked up Marcus, the big black dildo that Jess had got me, I lifted it to my mouth. In my mind there was a strong muscular man in front of me, dangling his 10 inch cock in front of my face. I wrapped my mouth around it and took it in.

I gave it head, covering it in my spit. Taking it in as far as I could, pushing my gag reflex to its limits. Whilst I sucked it off I reached for the coconut oil, my preferred lube, it smelt gorgeous. I placed the fake penis between my legs and lubed my asshole, groaning as I pushed a finger into me, and then added more, but it was the cock I really wanted.

I lifted the cock up, adding more spit, and then placed it under me, holding it up, placing the tip against the opening between my two cheeks. I lowered myself down. The anticipation of it entering me had me shaking, my legs trembling as I pushed down. I felt it stretch me open, the pleasure coursing through me. My hole stretched wide around the head as I forced it in. I gasped as a stabbing pain encircled my ring, the widest point testing my limits. I wanted it though and pushed harder, knowing what ecstasy awaited.

I rushed it and pushed down hard, the pain burned before my hole welcomed the thick cock in. I groaned loudly as it broke through, my ring accepting it all, the cock sliding deep inside me.

"Oh god," I moaned. I gripped my own cock and started stroking it as I slowly forced the hard rubber cock deep inside me, my round firm bum nearing the floor.

I started sliding up and down it, riding it as I wanked myself off, my hole felt so tight around the thick shaft. I loved it when I was stretched wide. I lost control, vigorously stroking myself whilst being fucked by the dildo. I knew I wouldn't last long. I was soon groaning loudly and cumming into my hand, catching it all as it ejaculated hard from the tip of my throbbing penis.

I struggled to hold myself up on my shaking legs as I licked the cum clean from my hand, swilling around in my mouth, dribbling it down my chin, before swallowing what was left. I loved cum, fantasised about being covered in it.

I realised I was nearly sat on the floor, the 10 inches nearly fully inside me. It felt so amazing, I was full and satisfied. I lifted myself up, my legs, weak from the orgasm. I groaned loudly, the penis coming out almost as good as when it enters. My asshole slid up the thick shaft, snagging on the bulbous head. I pulled free, groaning again as it popped out of me. I fell to the floor, bringing my stocking covered knees up to my chest and holding myself tight.

My desire to be really fucked now growing stronger and stronger. I needed it soon.

...

The day of the hen do came around so slowly, it had felt like it would never arrive. I had got more and more nervous the closer it had got, but now stood in Jessica's bedroom I was just bubbling with excitement. Of course there were nerves under the surface, but the thought of getting dressed up again had me giddy.

"What time are we meeting them again?" I asked, for the hundredth time. Jess laughed.

"For fucks sake babe," Jess said. "You're like a little kid. Just be patient. We're meeting them for dinner at six."

"And you're sure this is a good idea?" I said.

"Definitely," Jess replied. "It's going to be great. I can't wait to be out with my new girlfriend."

I laughed, it sounded weird, but felt right at the same time. "Me too," I said. "Where's this outfit then? Or have you lost it in this shit pit." I looked around at her room, the clothes were everywhere. Jess wasn't the tidiest person in the world.

"Hey!" she said, giving me an evil look, I winked at her and she smiled. "It's not easy being this hot. I don't have time for such luxuries as tidying."

"I noticed," I mumbled, trying to find a spot to sit on the bed.

"Complain again sunshine and you'll be wearing a bin bag tonight," she said, moving items around on the bed. I watched her movements. She was wearing a pair of small white shorts and a t-shirt. Her legs, long and slender, were mesmerising.

"Sorry," I said. "I wish I had legs like yours." She glanced my way and smiled.

"Don't underestimate those pins of yours," she said. "And in this tonight you'll be gorgeous." She held up a skirt.

I took one look and smiled. "Let's get to work," I said.

"Did you bring them?" Jess said.

"Of course," I said. In the weeks in between Jess had brought me a present, an expensive present, which even though I was incredibly grateful, I still gave her shit about. She was always spending money on me. She said she couldn't resist. She had wanted me to get used to them, and I had. Many hours spent walking around my apartment.

"Good," she said. "Let's make you gorgeous."

Jess chatted away to me as she did my make up and hair. I was glad I didn't have to wear a wig, it would have made me more self conscious. When she had finished I stared at myself in the mirror, to me I had been fully transformed into a woman. I had feminine features anyway but this just made my look perfect. She had kept it natural, not too heavy.

"Gorgeous," Jess said. She stood behind me and bent over and kissed me on the cheek.

"Thank you," I said. I couldn't help but smile at my reflection.

"My pleasure," Jess replied. "Now for your underwear. I stood up and she passed me a matching black bra and panties, delicate and pretty. I stripped down and put them on. With a couple of magic fake breast fillets I had some curves going.

"Now these," Jess said, she handed over some dark tights and I put them on, covering my long slim legs.

"Oh I do like that," I said, as she passed me the skirt. It was yellow and black plaid, pleated and short. Next was a long sleeved black turtle neck top. I put them on too.

I stood in front of the mirror with Jess cooing next to me. I looked good and felt great.

The skirt looked amazing, high on my slender thighs and up around the top of my hips. The top looked great too, it was tight and highlighted my flat stomach and breasts, even these looked real.

Jess squeezed my bum cheek, her hand up my skirt. "Looking hot," she said. I smiled back at her in the mirror.

"Thank you," I said, blushing.

"Now the best bit," Jess said. She grabbed the bag I had brought and pulled out the thigh length leather boots she had got me. They looked expensive and probably were.

I had already moaned about her spending so much money on me, but she said she wanted to, she could afford to treat her best friend. She owned a florist in an affluent part of town, it was her parents before they retired early and handed it down to her. She didn't even work much these days, she had hired people to do all the hard work, very entrepreneurial.

"Put them on now," she said. "I want to see them on you." I obediently slipped them on and posed for her again.

"They feel amazing," I said. They made me look taller, my legs longer and more prominent.

"Worth every penny sexy girl," Jess said. "I'm going to go have a shower, and get ready. Won't take me long." I watched her go and sat on the bed. I waited for her, she was right it didn't take her long.

When she was done she looked amazing as always. She had on a pair of black skinny jeans with black strappy high heels. A small black crop top, with a lace trim by her stunning cleavage. Her flat stomach looked amazing. She finished the look with a small leather jacket and a simple black velvet choker round her long neck.

"Wow," I said. "Not too shabby."

"Thank you," she said. "I reckon we could turn some heads tonight. You definitely." She came over and brushed some fluff off my shoulder. "Maybe even get some of the cock action you want." She smiled at me, looking deep into my eyes.

"I wish," I said, I looked down, unable to hold her probing gaze. Just the thought made my own penis twitch.

"You never know babe," Jess said. "I'm making finding you pleasure my priority."

"If I wasn't so horny I might be offended," I said, laughing. "What's in it for you anyway? I'm not paying you to be my wingman."

"Don't you worry about me," she replied. "Let's go get this train and get some wine on the go."

...

We had a great journey up, I was incredibly excited to be out as Millie, and didn't get any uncomfortable looks. In fact, I got some admiring glances from quite a few eligible hotties. My shy glances, and then my blushing as they smiled at me made Jess laugh.

We chatted and laughed on the way up, both excited for an evening out together. Jess was very thankful for me agreeing to come along, she had been really dreading going on her own.

We met the other six girls in the hotel restaurant where we were all staying. Jess and I had a twin room where we had briefly dropped our bags off. Introductions and hugs were shared, they all seemed lovely, even Laura.

Jess had failed to mention how pretty she was. Blonde and petite. I could see what Jess meant though, she was a bit stuck up, she came from money and made it obvious, but I think the excitement of the evening was making her relax a bit. And I'm sure the endless supply of wine during the meal helped.

I was sensible, hiding the fact I was only sipping at my wine. I had to be careful, too drunk and I might lose character. I had a feeling though the young women we were with probably wouldn't mind the truth.

It was a lovely meal, which finished with a surprise from Laura. She had hired the penthouse for us all to have pre drinks before we went to a club. We were all giddy with excitement as we entered the large penthouse to find bottles of champagne on the table for us.