Rush Hour Crush

Dan suggested a few options but he soon got sidetracked into talking about sex and how that might work between us. He kept asking if I was gonna take her up dick up my ass or if I knew whether she was pre- or post-op. I said it didn't matter and I was just into her whatever, but I couldn't help but think about it. Was I really into having her being on top and was I really into the idea of her cock? I decided to steer things back to where I should take her on a date.

I decided on a sunset picnic in the park that looks over the city. It was close to where we lived and the views were amazing at sunset. It also meant I could spend the day cooking some picnic snacks and it would be a good place for us to chat together as we watched the sunset.

* * *

I spent the afternoon prepping for our date, I cooked some mini quiches, veggie rolls, and cookies for our picnic. I spent some time cleaning the flat making sure it was presentable when we made our way back to mine after the picnic. As a joke I put a new toothbrush in the bathroom for Chloe. Once I was happy with my efforts I gathered everything into a bag and headed out to meet Chloe.

I found a nice spot overlooking the expanse of the city below. You could see the river winding its way out to sea and huge skyscrapers jutting out along the riverbanks. I laid out the picnic blanket and lit a few candles that I'd bought with me helping to set the scene. The food was in the bag so it stayed cool, but I got a bottle of wine and two glasses ready for when Chloe arrived. I checked my phone and saw that Chloe had texted me saying she was just walking into the park.

I saw her straight away walking through the park towards me. Her hair was blowing in the slight breeze and her figure looked amazing in a short blue summer dress showing off her curves. My heart beat fast as I got excited just thinking about how those lips felt on my dick last night that I got noticeably hard. I tried to stop thinking about it but I couldn't help it, she sent me wild even from the other side of the park.

I stood up when Chloe got close and she noticed the bulge that had formed in my shorts.

"Someone's pleased to see me again," she teased, as I blushed awkwardly. "No surprises at what I'll be having for dessert."

"I've baked cookies actually," I said playfully. Chloe looked a little shocked and softened from her flirtatious banter giving me a kiss and a hug.

"Well aren't you a cutie."

I gestured for her to sit as I started to open the champagne. Now I knew Chloe wasn't the type to expect to have all the fineries, but I wanted to splash out on a nice bottle for us to share, and this didn't go unnoticed.

"You've got good taste. If I was a betting girl I'd say you were trying to seduce me."

"Damn you caught me."

"No, please carry on! I'll let you know if it's working."

We drank our champagne and ate some nibbles whilst she told me everything that had happened since we'd seen each other the previous night. In truth not a lot had happened. She'd taken Yasmin back to her place and made sure her boyfriend knew where she was and then they'd both gone out for brunch. I asked her more about her friendship with Yasmin, and conversation drifted to music we both liked and films we'd seen recently. It was all very natural and whilst we didn't agree on everything we did have a lot in common. The previous night we'd barely scratched the surface so it was nice to get the chance to talk and laugh together.

The evening flew by quickly, the champagne had gone down even quicker and before long we were onto our second bottle as we munched through the quiches and picnic food I'd spent the day making. Chloe was really impressed with my cooking and I was pleased the food had gone down so well. We'd already agreed that I'd cook a full meal for us both next time.

The air wasn't quite as warm this evening so we decided that we'd have dessert back at my place and made our way back through the park towards my flat. As we walked through the streets holding hands I felt a bit nervous about bringing Chloe back to my flat. I knew I liked her and this evening was proof that we had a lot in common, but being with a trans woman was new to me and I wasn't sure if I'd like it. I was scared I wouldn't enjoy being intimate and that we'd part ways. This thought made me really sad and made me more nervous about what was about to happen.

Chloe could sense my sudden silence and asked if I was ok, and I explained a bit about how I was feeling. She stopped walking and kissed me gently with her plump lips that drove me wild.

"We'll go at your pace, whatever your comfortable with, besides I'm only here for the cookies."

I laughed and instantly felt less pressure about the whole thing and when we arrived back at my flat I was feeling excited to have Chloe in the place where I lived. As I closed the door we instantly locked lips and made our way to the sofa moaning and thrusting as our hands started exploring eachothers bodies.

Chloe went straight into massaging my erect penis through my shorts. Her body rubbing against mine felt amazing. I massaged her big tits and kissed her neck as our bodies pushed and pulled against one another. I unzipped her dress which revealed a matching set of white silky lingerie underneath. I saw for the first time the outline of a bulge in her pants, and seeing that only made me more excited, I was no longer scared or nervous about being with a girl like Chloe, I was turned on! Her curves looked amazing as the thong framed her beautiful big bum. On instinct I spanked it which only encouraged Chloe to pull away at my clothes exposing my naked body.

We savoured the sensation of skin on skin for the first time as we kissed each other more and more intensely biting playfully on her lips. I could feel my rock hard cock pushing against Chloe's cock and it felt great. I'd felt it the night before when we were dancing but at that point I didn't know, and now I didn't care, I wanted her so badly. As we humped and thrust against each other Chloe's plump lips made her way down my neck kissing my softly at first but as she made her way to my pants the kisses became wetter and more intense.

She ripped my pants off to expose my throbbing penis beneath. There was that feeling I'd been thinking about all day, yearning for, as I baked and cooked in preparation for our date. Those lips wrapped around my dick, bobbing up and down with a mouthful of me. In front of me I could see Chloe kneeling on the floor and her big ass staring up at me in that silky thong and her head bouncing up and down as she took my cock deeper into the back of her throat.

I lifted her head off my cock and a train of spit and precum followed as leant to those wet lips enjoying the musky taste. I wanted to return the favour so I guided Chloe into position and started kissing her crotch through her pants, teasing her with my mouth. Kissing her cock through the silk pants felt great and I could feel a slight wet patch where Chloe's precum had escaped. I wasn't sure where to start, but I removed her pants anyway revealing her big throbbing dick, but unlike mine it wasn't masculine and veiny, it was feminine, big, but really beautiful and seeing Chloe sat there with her erect penis made me want to pleasure her.

"Are you sure about this?" she asked.

I didn't reply verbally, instead I opened my mouth and took her cock in my mouth and went on instinct. I used my hands to guide her penis and pleasured her with both to start with, but as I got into a Rhythm I just used my mouth. Chloe moaned as I sucked away and the sound of her getting turned on made me want to take her deeper and faster. I played with my tongue moving it around her shaft teasing her cock as I sucked. She was wet with my saliva, but there was also a fair amount of cum leaking out of her.

"Oh yes, I'm so wet. This is great babe!" Chloe moaned softly.

I moved my mouth faster and faster over her cock bobbing up and down feeling her tip touching the back of my mouth each time. As I sucked faster Chloe thrust her cock which caused me to pull away for a moment, choking a little on her big dick.

"You ok?" she said with concern.

"Why don't we take things to the bedroom?" I asked.

We got up from the sofa and made our way into my bedroom, unable to keep our hands off each other as we made the short walk from one room to the other. We were kissing and grabbing each other's cocks and playfully spanking each other. About a third of the way through the journey Chloe got on her knees and started sucking and going to town on me again. It was raw and feral, we couldn't control our desires enough to make it into the next room without pleasuring each other.

We both fell onto the bed in a passionate kiss and continued our fondling of each other's bodies. Chloe started moving into a position on the bed and guided me into what I knew was "69" where we could both pleasure each other at the same time. Chloe was first to put my cock in her mouth and was lying on top of me, her tits were pressed up against my torso and her cock was dangling above my mouth. I took a moment to enjoy her smell, a musky pheromone that made me want her cock in my mouth even more.

We pleasured each other in this position for some time, before Chloe stopped on my cock for a moment and started kissing my balls. She took one in her mouth and sucked on it for a moment and then made her way back to my cock. This reprised sensation made me cum almost instantly and I could feel Chloe sucking and licking every drop of cum from my dick. Chloe still hadn't cum, but she'd said sometimes her hormones meant that it wasn't always possible, but I kept going determined to pleasure my lover.

As I sucked her beautiful she-cock, Chloe was exploring my groan with her tongue and teasing my bum. I'd never been with a girl like Chloe and all of my previous girlfriends had been against anything other than vaginal sex, so feeling Chloes tongue and lips around my ass felt amazing. I wasn't ever going back to pussy, Chloe was all I needed now, and as I sucked her cock I took my cue and began to finger her ass. Chloe moaned with pleasure as I teased my fingers deeper into her ass, until she finally came. My mouth filled up with Chloe's cum, warm and smooth as it hit the back of my throat. I had no choice but to swallow her load and I felt the thick creamy cum make its way down inside me.

I could have ended the evening there and been a happy, no, more than happy, guy, but as Chloe took her lips away from my ass and looked at me. We scrambled to lock lips again in a way that confirmed this was only the beginning.

"So how are you finding it with your first trans girl?" Chloe asked as she pulled her lips away from mine.

"It's amazing, you're amazing!" I said.

She batted her eyes playfully and we kissed again. She held my cock as we kissed.

"Do you have lube?" Chloe asked playfully.

I'd got a bottle hidden away somewhere, and pulled out some condoms. Chloe lay on the bed with her big round ass poised ready and stroking her nipple waiting for me. It was enough to make me cum there and then. She laughed at her very obvious seductive behaviour and the effect it was having on me as I crept towards the bed with my cock rising to attention again.

I was amazed at how natural this all felt, and was kind of pissed that so many people made such a big deal of non-hetrosexual sex and relationships. Chloe was a beautiful woman born in the wrong body and everything we were doing together felt so perfect. I lay on the bed beside her and kissed her again, but this was more passionate, trying to emulate how I felt. We looked at each other for a moment enjoying the romance of my new lover and I think Chloe could sense this too.

"I'm having a great night, thank you." I said to her as we shared this more tender moment.

"Me too," She kissed me, then a playful look came across her "now fuck me!" she giggled.

Electricity came between us as our bodies humped and thrust against each other kissing and grabbing at our bodies. I wrapped my mouth around her breasts as she held my cock in her hand. I wanted Chloe so bad.

I put the condom on and squirted the lube over my cock and her bum giving her a little spank as I did. Then I gently positioned myself inside Chloe. I'd never done anal before and it felt incredible as her tight ass took my cock inside of it slowly sucking it in. I moved slowly to begin with, but I could tell Chloe wanted me to go faster and that I didn't need to be as cautious. I started thrusting with more vigour, feeling my cock penetrating deep into her ass as she moaned and writhed in pleasure on the bed. Chloe lay pressed on the bed moaning as my cock pounded her ass. She gripped the sheets and pushed back, thrusting her ass as I pumped her from behind. I was in heaven, all my earlier doubts were gone as ecstasy took over.

We changed positions slightly so Chloe was on all fours with her big ass in the air as I pumped my cock faster and deeper inside her. The tightness of her ass felt amazing and we quickly got into a rhythm together as we spoke the same erotic languge to the same seductive beat.

As I fucked her I grabbed Chloes tits squeezing them in my hand. I felt like the luckiest guy on earth as her ass swallowed me deep inside her. Chloe was loving the feeling and called out "faster" and "harder" as I thrust. She obviously loved being fucked and liked it when I got more intense, spanking her ass or pulling her hair really drove her wild. At one point I grabbed her cock and started jerking it as we fucked, which sent her moans in a whole new direction. I could feel her cock getting harder in my hand and precum dripping from her.

"oh I'm so wet!" she screamed as my cock ploughed her ass and my hands held her cock.

Chloe turned her head and kissed me like a diver gasping for air. Her moans grew louder and she called out more and more loving every second as I fucked her ass like I'd never done before. We were so in sync with each other, our bodies were no longer two seperate people, but one sexual organ throbbing and thrusting on the bed.

We changed positions again, but I wasn't sure I could last long. Chloe was so hot when she moaned and I wanted it to last all night, but it was just too arousing. As Chloe sat on top of me this time facing me we kissed as we returned to our sexual rhythm and Chloe did more of the thrusting this time, squeezing her ass tight as she did so. Her big tits bounced up and down in front of me and her rock hard cock bobbed as it glistened with precum. I held it again feeling it throb in my hand and kissed her nipples as we continued to fuck.

Chloe couldn't last much longer and cum squirted up and all over the two of us as we continued to thrust. A loud moan came from Chloe as she squeezed her ass tight in pleasure. A few moments later, I came inside her. Chloe squeezed her ass again and we kissed as our bodies recovered from the intense sex we'd just had. Slowly Chloe lifted herself off my cock and we lay together enjoying the stillness. We were both wearing the effects of our lovemaking covered in each other's cum and perspiration.

We made our way into the bathroom and turned on the shower and stood together under the flowing water. The water felt nice against my skin and we both took turns at showering each other. At first we were concerned with cleaning, but quickly we were massaging and making out under the shower head. I pressed Chloe against the side of the cubicle and grabbed her cock as we made out. It was flaccid at first, but as I started to play with it, the harder it became and so did my own cock. Our kisses became more and more intense as our lust for one another intensified again. As I wanked her off, Chloe's fingers made their way into my asshole which took me by surprise, and whilst I couldn't be sure where things were going, I didn't want them to stop.

The last 24 hours had been a series of new experiences and so far I'd loved every single one. Chloe was an amazing lover and I was really falling for her. As her fingers penetrated and played inside me, I kissed her soft lips and played with her breasts. I shut the water off and leant against the cubicle ready for her. Chloe took her cue, parted my cheeks and slid her wet cock into my ass. I tensed up, but Chloe paused and held me for a moment.

"Just relax, push against me slowly as I penetrate." she said.

She tried again and her cock slid inside me. It hurt, and the pain pulsated through my body, but as I pushed against it the pain slowly became more warming and more pleasurable. Chloe was very gentle as she thrust back and forth letting me get used to the feeling. After a minute I was really enjoying how it felt and started to moan in pleasure. Her dick pushed its way further inside me back and forth slowly and I was really beginning to enjoy it. With each pump of her cock Chloe slowly sped things up and started to fuck me a bit harder. Our wet bodies slapped against each other as Chloe fucked my ass hard holding my hips as she did. She spanked my ass hard.

"You like that baby? My dick inside you?" Chloe said as she fucked me harder and faster.

I nodded my head.

"Say it!" she instructed "I want you to tell me."

"Oh god, It feels so good! Fuck me harder." I called out and moaned as she did so.

Chloe thrust harder and faster as we clapped against each other in the shower cubicle, not that long ago I'd been alone fantasising about this mystery girl, and here she was slamming my ass with her cock. I turned to look at her and she smiled before pulling my chin close and kissing me. We fucked in a perfect rhythm togther enjoying this new sensation was turning me on too, my cock was rock hard as Chloe pushed her cock deep inside me. Chloe had noticed and started wanking my cock as she thrust her cock inside me. Her soft hands stroked my cock in time with her thrusts. Never had I been so submissive during sex, I was being fucked and having my cock wanked off at the same time.

Ripples of orgasms were flowing through my body and within minutes I was spraying my load across the tiles, but Chloe kept going on my ass. I squeezed hard as she pumped away and felt the pleasures shoot through my body. I held my hands behind me and grabbed Chloes ass pulling her closer than before, forcing her movements to be smaller but more intense. A few seconds later I felt another new sensation as Chloe's dick emptied a warm load in my ass.

As she pulled her cock out from my ass, the cum seeped out too. Chloe spanked my ass and I turned to kiss her. I'd never felt such pleasure with any other person, it was one thing having someone pleasure my cock, but having my ass and cock at the same time was another level. I couldn't wait to do it again and again with Chloe. I may have been a top before but I was Chloe's bottom from now on. I turned the shower on again and rinsed the body fluids away. I held Chloe in my arms as the water fell over our bodies. I felt content, safe and truly happy holding her close to me, and kissed her.

"Still fancy a cookie?" I asked.

"I think I've had all the desert I can handle." said Chloe with a wink.

"Yeah it's been amazing." I said

"You're a natural bottom babe," she said, kissing me "How was your first time with a TGirl?"

"I loved it, you can fuck me anytime, anywhere." I said.

"Ditto babe." she said and softly spanked me ass.

We left the bathroom and enjoyed the rest of the champagne in bed together, naked and listening to our favourite songs.