With a Friend's Help Pt. 02

We had just got in from Jessica's brother's girlfriend's hen do. What a night it had been. A lovely meal, some male strippers in the hotel penthouse, and lots of dancing and laughing. The highlight was me sucking off one of the strippers and swallowing his cum down. A memory I could never forget.

The rest of the night went smoothly, if not slightly disappointing. Despite our best efforts, we came back to the hotel room alone.

"Sorry Jess," I said. My situation had made things more difficult. I couldn't just have anyone I wanted, I had to tell them I was transgender before there was any intimacy, and that wasn't the easiest conversation. And I was still quite new to all this.

"For what?" Jess said. Looking over. She still looked amazing in her tight black jeans and black crop top, her jacket was already on the floor. I cringed at her messy habits, biting my tongue.

"Making it difficult when we were with those guys," I replied.

"Don't you fucking dare apologise," Jess said, making me startle slightly. "It's not your fault you have to worry about people's levels of tolerance. You were amazing tonight."

"Thank you," I said. "Do you think anyone noticed?"

"Not a chance," Jess said.

I lay on my back in the bed, pulling my yellow and black plaid skirt down and straightening it, flattening my long sleeve black top against my flat stomach. Jess watched me from the doorway.

"That was so hot tonight?" I said. I thought back to sucking off the stripper. My first time.

Jess walked over to the bed and laid down next me. She ran her fingers up my arm, my senses on overdrive. Every finger sending sensual pulses to my brain.

"How did it feel in your mouth?" Jess asked. "Describe it to me."

"Really Jess?" I asked, feeling myself flush. Her fingers ran through my long brown hair, brushing the strands away from my cheek.

"Just tell me," she pushed. "Tell me how it felt."

"Amazing," I said. "It felt so hot."

"It looked even hotter," Jess said. "You were a natural." She winked at me.

"Thanks," I said, laughing. "A natural cock sucker. My mum will be proud." Jess laughed too.

"Would you have let him fuck you in front of everyone?" She asked.

"No! For fucks sake Jess," I said, a little too quickly.

"Don't lie to me Millie," she said. She knew me too well. I couldn't lie to her, and I didn't want to. It was that pleasing thing again, I wasn't sure where it had come from.

"I wanted him to," I mumbled.

"Wanted him to what?" Jess said. I wasn't sure what was going on, she wanted me to tell her what I wanted. I couldn't help myself.

"I wanted him to fuck me Jess," I said. "In front of everyone." My cock strained in my panties and tights. "I wanted it so bad."

"Are you hard thinking about it?" Jess said, looking down at my lap. I laughed nervously, then saw her eyes.

"You're fucking serious?" I said. The truth was my cock was raging under my skirt.

"Sorry," she said, quietly. Looking down the bed. "I just want to share the experience with you. My best friend. I'll stop if you're uncomfortable."

The truth was I was so excited sharing this with her. Also her dominance was turning me on more. She knew this of course, but I loved her, and wanted to experience this with someone, with her.

"You don't need to stop," I said, quietly.

"Good," she said. "Are you hard under that sexy little skirt of yours?"

"Oh god. Yes," I groaned.

"That's better," Jess said. "Now show me, take it out."

"Jess, I.........." I started.

"Take it out," Jess interrupted forcefully. I couldn't stop myself as I lifted my skirt. I obediently lifted my bum and pulled my tights and panties down, my hard cock springing out and slapping against the raised skirt. It was so hard.

My hard 6 inch penis stood tall, my groin free from hair. I liked to keep myself shaved all over.

"Good girl," Jess said. "Did you want to take it out whilst you got face fucked?"

"I did," I said. I couldn't stop myself from taking it in my hand. My whole body trembled as I touched it. "Oh fuck Jess." I started stroking myself.

"That's it baby," Jess said into my ear. "Cum for me like he jizzed in your mouth. Think of all that cum inside you. Inside your flat sexy stomach."

I played with myself as she watched, her hand ran over my upper body. I started slowly, but I was way too turned on. Jessica watching me too, it was too much. I sped up, frantically wanting to orgasm.

"I'm going to cum," I groaned.

"How did it feel gagging on that big throbbing cum squirting cock?" Jess said, her breathing heavier. That was it.

"Oh god," I said. I orgasmed, cum ejaculating over my skirt. I closed my eyes and groaned, my body shook. It was so intense, the pleasure so strong as it attacked my senses.

Jess watched intently next to me as my squirts got less intense, eventually just slowing to a weak dribble.

"That's my girl," Jess whispered, close to my ear again. "I'm going to get ready for bed." She jumped up and hurried to the bathroom, leaving me lying on the bed, covered in my own cum, still trembling, my heart beating fast and my breath rugged.

"Fuck," I said to myself. That felt good, but it had also confused me. What was Jess doing? What did this mean? Something told me she was only just getting started with me, and it excited the fuck out of me.

I got up and sorted myself out. Taking my clothes off and putting on a long t-shirt, I kept my panties on. I crawled into bed and waited for the bathroom to be free. Jess was taking a long time. When she finally came out she was in a vest top and some pyjama bottoms.

"You took your time," I said. She went over to her own bed and got in as I stood to go to the bathroom.

"I had some things to take care of," she said. She didn't add any more. I knew what she had done and was slightly annoyed that she hadn't done it next to me. I looked at her suspiciously, and then went and got ready for bed.

Not long later I was lying there and staring up at the ceiling, my mind whirling with the evening excitement.

"I'm going to find you someone," Jess suddenly said.

"Thanks Jess," I said, "but I'm not completely desperate." I winced at my own lie.

"Yeah right," she replied. "I saw you drooling over that blonde bit in the club. I'm surprised you didn't start humping his leg." I laughed, it was true!

"Oh you bitch," I said. "I was in there until you dragged me off for a dance."

"I think you were too," Jess said. "and that's the problem."

"Doesn't sound like a problem to me," I mumbled.

"It's not that I don't think you can pull," she said. "It's just making sure he's the right man. That's he not bothered by who you are."

I lay there thinking. Jessica was right as always. It was one thing to pick someone up, it was another to hope they didn't mind that I had a penis.

"I hope I haven't hurt your feelings," Jess said. "It's just that I love you and I want you to be happy." A tear welled up in my eye.

"You haven't," I managed. "And I love you too Jess. We should go to sleep."

"Yeah. We should," She said. "Night cock sucker." We both laughed.

"Night," I said, when we finished laughing. I thought it would take ages to sleep, but the events of the evening had tired me out. I was soon fast asleep.

.....................

It was now the middle of the week, and I still couldn't help thinking about the cock I had sucked, and what happened with Jess, as I waited for her in the coffee shop.

I was out as Tim. Still not happy with my skills at transforming myself. I was getting close, but the make up part was holding me back. Work was also the problem. I wanted to be Millie full time, but how did that work. Did I just turn up for work one day in women's clothes, or did I speak to my boss. The thought made me feel sick.

I just had jeans and a blue t-shirt on. Oh, I had some nice lace knickers on underneath, that was just normal for me.

I looked up and saw Jessica enter. I also saw a few heads turn her way. She took her sunglasses off and flicked her hair off her face. She was all business. A simple white blouse, black pencil skirt, and black high heels. She looked fantastic. Her long slender legs, and her ample bosom straining the buttons on her shirt. She was everything I wanted to be. She came over.

"Very sexy," I said, as she neared. "Those shoes are amazing."

"They are, aren't they?" Jess replied. Sitting down opposite me. "I got them yesterday. You can try them on sometime."

"I'd like that," I said. "Your week been okay? Pretending to be busy!" We had both been very busy the last few days, I had only spoken to her briefly once so far this week, which was rare for us. It had nothing to do with what happened at the weekend though. Sometimes life was just busy.

"It's very busy," Jess replied. "We've been trying to catch up with orders, but they keep coming. Definitely need this break."

"Hope you get on top of it," I said.

"Hope so too," she said. "How have you been?"

"I'm good," I said. "Been busy too, but it's all boring crap. Just looking forward to the weekend. What are we up to?"

"Not sure yet," Jess said. "Working on a few things." She had that twinkle in her eye I didn't trust.

"What are you up to?" I asked, suspiciously.

"Wouldn't you like to know," she said. The waitress came over at that point and we ordered a light lunch and coffees. I watched as Jessica flirted with her.

"She's cute," she added when the waitress walked off. I couldn't help the pang of jealousy that rippled through me. Ever since Saturday night I was a bit all over the place.

"So what have you got planned?" I asked, again.

"Just trying to set up some company for us," she said. "Take it you'll be out as Millie."

"Definitely," I said. I liked the sound of company, after the cock I sucked on at the weekend, I wanted more. "What company?"

"Don't get your hopes up yet," Jess said. "I'm not sure they're free this weekend."

"You make me sound desperate," I said.

"Cause you fucking are," Jess said laughing. I laughed with her. It was tragic, but true.

"True," I mumbled.

"Whatever happens we'll have a great weekend," she said. "I've got a few tricks up my sleeve."

"Sounds ominous," I said.

..............................

It was Saturday night, Jessica's plans had failed, and we decided to have a movie night instead. Neither of us had the energy to go out. Jessica must have apologised a hundred times already, it must have been a good plan. She said she was rearranging it though.

This time I had done my makeup, with Jessica's guidance, and I thought I had done a good job. I had on a pair of tight blue jeans and a yellow cropped vest top. I felt good in it.

We watched a film, and ate a shameful amount of popcorn, crisps and sweets. By the end of the film Jess had her head on my lap, and I was playing with her hair. She kept looking up at me, like she wanted to say something. She wasn't usually so shy, which had me worried.

"Just spit it out Jess," I said. I watched her form her words in her head.

"I feel bad that I haven't found you someone yet," Jessica said. "I promised I would." She couldn't hold my eyes, like I was disappointed in her.

"Don't be silly. I'm fine," I lied. Ever since the party I had wanted more. "And I told you, stop apologising."

"I know," she said. "But like I said before I want you to be happy. It makes me happy."

"I am happy Jess," I said. "I've got you as a friend."

"It's funny you should say that," she said, she sat up and turned my way, the glint in her eyes again. "I brought something for you the other day."

"For fucks sake Jess," I said. "Stop spending money on me."

"Well it's kind of for me too," she said. "You do trust me right?" She jumped up and headed to the door, she stopped in the doorway, waiting for an answer. She was wearing a small pair of black denim shorts, her long legs looked amazing. On top she had a white t-shirt with some band logo I didn't recognise.

"Of course," I said. "I think." I really didn't like the smile on her face as she disappeared from view. I found myself getting excited, she was up to something and I hoped it was good. I wasn't disappointed.

She hadn't been gone long, when her pretty face appeared round the door frame.

"You ready?" Jess said, her body hidden from view.

"Yeah. I think so," I replied. I wasn't ready for what she came in with, I gasped. Nearly laughed, but saw the serious expression on her face.

"Fuck me Jess!" I managed. Around her pelvis was a strap on cock, not a small one either.

"That's the idea," she said. She almost floated across the bedroom towards me, she stood right in front of me, the fake cock standing out. I was lost for words as she stood in front of me. "I want you to know how it feels, to be ready for the real thing."

"I'm not sure this.........." I started, but Jess interrupted me.

"It'll be fun," she said. I looked at her wearing the strap on, I had no chance to resist. She saw my body language and knew she had me twisted around her finger.

"Suck it," she said. "Show me how you sucked that stripper cock." She moved closer. The fake cock bobbing hard infront of my face. "Suck my cock."

Her dominance again turned me on and I reached out and took it in my hand. My other hand went to her thigh. Jess took it off.

"No touching," Jess said. "You're the one that's getting all the pleasure. Now fucking suck it."

I leant forward and took the cock straight in my mouth. Slowly running my lips up and down it, coating it in my spit. It was lifelike, veiny and shaped. I looked up at Jess as I sucked her off. She smiled down at me.

"That's a good girl," she said. "A good cock sucking slut."

"Hey!" I said. My mouth coming off the cock.

Jess gripped my hair and pushed the cock back into my mouth and down my throat. I groaned as it slid deep inside. I was a slut, I loved it, even though it was fake. I gagged as it went further down my throat. Jess held it a moment later before letting me back up.

I worked the cock with my mouth and tongue. My hand was between my legs, touching myself through the fabric of the jeans. Jess watching me was so hot.

"Mmm, looks so good," Jess moaned. "So good I want to fuck that pretty face of yours." I nodded eagerly, my eyes showing my need as they met hers.

Jess grabbed my hair and moved her slender hips forward, pushing the shaft of the dildo deeper into my mouth, the tip sliding down my throat. She started thrusting, literally fucking my face. I gagged and drooled everywhere, loving the feel, and look as she humped away.

I was so hard now, my penis straining in my jeans, I rubbed myself through the fabric. The strap on kept sliding deep down my throat. She stopped and I came up for air. Spit was all down my chin and chest, my small fake breasts damp.

"Do you want more?" Jess asked. I nodded eagerly. "Show me how much you want it and I'll fuck that tight little ass of yours."

I groaned loudly. Jess smiled. "I want it," I begged. My hands ran over my pert bottom, fingers pressing between the cheeks against my hole. I then grabbed the fake cock and started giving it head, sucking it off with extra motivation.

Jess moaned. "Such a good slut," she said. "I think you've earned your prize." She lifted me up by my drool covered chin and turned me round. She pushed my head down and bent me over the sofa.

"Get that tight little asshole out," she said.

I did what she asked, getting on the sofa and kneeling. I pulled my jeans and panties down together, they stretched between my thighs. My throbbing penis sprang free, dangling out. I spat on my hand and rubbed it on my asshole.

"I've got that," Jess said. I jumped and let out a long groan as I felt her tongue touch me.

"Oh shit," I moaned. No one had kissed my hole before, and it felt amazing. Jess spat and pushed her tongue into me. Her head bobbed as she fucked me with it. More groans escaped my lips as she put fingers into me, I lost track of time and how many fingers, as pleasure consumed me. I think there was lube involved, but I wasn't sure and didn't care. It felt so good.

"Fuck me," I begged, surprising myself.

"What was that?" Jess said. Getting up and leaning over me. I felt the cock between my legs.

"Fuck me Jess. Please," I begged again. "I am a slut, I want it so much." She pushed her pelvis into me. The strap on rubbing against my own hard member.

"Who's slut?" Jess asked. I groaned.

"Yours Jess," I said. "I'm your slut." I cried out as she pressed the tip of the cock against my opening. Pushing harder as it stretched me, a brief stabbing pain. She pulled back and pushed forward again, my bum hole stretching wide, more pain. I gasped as she applied more pressure and my hole gave way, it slid in. I groaned, so did Jess.

"Don't you forget it," Jess said, pushing deep inside me. She started to slowly fuck my tight asshole. I groaned and writhed as her hips thrust into me. I gripped my penis and started stroking myself.

"Fuck," Jess moaned. She slowed and pulled out, then thrust back in hard. Making me cry out. She did it again, before fucking me hard again. I could hear Jess moaning, she seemed to be getting just as much out of this as I was. Her moans grew louder. My own orgasm was growing.

Jessica's thrusts grew erratic, her breathing got heavier. She groaned loudly as she slowed down again, almost stopping.

I heard Jess let out a long moan behind me, I knew she had orgasmed. I desperately wanted to see and I tried to look around but she forced my head back towards the sofa. Starting up again. The cock continued the pleasant assault on my insides.

She pulled me up into her, the strap on now so deep inside me. She held me gently by the throat, my body stretched tight in front of her as she continued to fuck me, I was close to cumming. Her free hand found my hard penis and she started stroking me.

"Cum for me," Jess whispered in my ear. "I want to feel you cum with me inside you." She started stroking me faster, her hand tighter. I had no chance.

"I'm cumming," I groaned. My cock erupted over the bed. Jess watched over my shoulder as it shot out of me in spurts, all over her leather sofa. I was shaking all over. Jess stopped fucking me and just pushed as deep as she could, my body twitching against her.

"Lick it up slut," she said. She let go of me and pushed me down. "Clean that mess you made."

I did. Licking up my cum from the leather fabric, hunting every last drop like a dirty cum slut. Lapping it up eagerly. My body still shaking.

"Good girl," Jess said. She pushed deeper inside me, and I groaned. She then pulled out, leaving my anal cavity empty and void. Jess flopped down on the sofa next to me. "Now clean it off."

"What?" I said, knowing full well what she wanted.

"Suck it clean," she said. "Taste that asshole."

I did what I was told, sucking it off again my mouth working away on the cock, licking it and sucking my anal fragrance off it. I wanted it all. When I was done I sat up next to her.

"That was fun," Jess said.

I groaned in agreement. My asshole felt nicely satisfied.

"It was," I said. "Thank you Jess." I looked at her and she smiled.

"My pleasure babe," Jess said. "If my next plan pays off you'll be thanking me even more."

"Sounds intriguing," I said.

To be continued.