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There’s a fair bit of backstory here. I’ll try to mark it as BACKSTORY, CLAIRE’S DESCRIPTION, BACKSTORY (continued), and SEXY TIME. Then if you don’t care about the backstory you can just find her description and the good stuff.

Hope you enjoy.

Apologies for any spelling errors, I wrote this up on mobile and caught most of the autocorrect changes.

BACKSTORY

My friend was having a party. I don’t remember what it was for, he seemed to have them quite often. I usually don’t go but every once in a while I’ll show up. It’s almost entirely people I don’t know, but if someone I know is going I’ll at least have someone to talk to. Another friend of mine was supposed to be there but he bailed at the last minute. The only person I knew was the host. It was going to be one of those awkward nights. I had a few drinks and worked my way into a couple of conversations as the night started out. It was a dark night and a small group of us ended up outside passing a couple of joints around. As the weed ran out people made their way back inside. There were only four of us left, my friend, his coworker, her roommate, and me. I sat on the porch railing, and lit up a smoke.

“Oh, good,” the roommate said, “I’m not the only smoker this time.” She lit up her own smoke and the four of us talked for a bit. I don’t remember what about, most likely the latest Marvel movie. Soon my friend and his coworker went back in, leaving me and the roommate outside smoking.

“I’m Claire,” she told me. I introduced myself as well.

CLAIRE’S DEACRIPTION

I should stop here and describe Claire. She was fairly tall, nearly 6’ which is still shorter than me. She had long blonde hair flowing over her shoulders. She was wearing a tight halter top that showed off her breasts. They weren’t huge, but they weren’t small, there was enough there that they bulged significantly when she crossed her arms. She had a flat stomach, round hips, and a nice round ass. She had long semi-toned legs coming out of her daisy duke like shorts.

BACKSTORY (continued)

“I don’t normally come out to these things, but my roommate insisted.”

“Me neither. I’m not really one for large groups of people,” I replied.

“At least it’s not crowded out here,” she stated.

“That’s true.” The sound of the party could still be heard from the porch, but it was dark and secluded out in the country. We stayed outside smoking and chatting for nearly two hours before a small group came out to smoke another joint. We joined in and hung back until everyone had gone back inside before lighting another smoke and resuming our conversation. We talked easily for another hour or two and found out we had a lot in common. At some point our conversation moved to the stars. There were a lot more in the country than in the city, but the porch light and lights from the house still obscured some of the amazing night sky. I suggested we take a walk to where the road dead ends at a farmer’s field for a better view. Claire loved the idea and took a moment to let her friend know where we were off to.

It was only a few minutes down the road and we sat up on the guard rail. I sat first and she sat down right next to me. We each had another smoke while I pointed out some of the planet, stars, and constellations that I knew. I was trying to point out one of the constellations but she couldn’t quite see it. She leaned her head in right beside mine to see where I was pointing. I turned slightly toward her, the light from the almost non-existent moon highlighted her features. She must have noticed my glance because she turned slightly toward me. My heart was pounding and I turned a little more and kissed her. She paused for a second before kissing back. The hand that had been pointing to the stars fell onto her thigh. I don’t remember how long we were there, but it was a greasy and intense make out session before we decided we should head back to the party. We chatted a bit longer and exchanged numbers before their cab came to pick them up. I have her another quick kiss, and she was off. I stayed the night at my friends place, not in any state to drive home, replaying the night in my head over and over. I was glad I had went out.

When I got home the following day we were texting back and forth quite a bit. Mostly just casual chit chat, but occasionally mentioning how much fun we had the night before. I suggested we meet up again that night and grab something to eat. She eagerly agreed. I picked her up in the evening from her apartment building. She was wearing a short black dress and high heels. Now she seemed as tall as me.

We went out for dinner and had a great time. It was crazy how casually the conversation flowed. We ate and then walked around town a little bit. The date couldn’t have gone on long enough, but eventually it ended. I drove her back to her apartment, parked, and walked her to the door. I said goodnight and gave her another kiss. Not a make out session like the night before, but a long and lingering kiss. She seemed a little nervous. I had hoped she’d invite me in, but she didn’t. We said our goodbyes and I headed to my car as she went into her building.

I was barely in my car when I got a message from her, “I had a great time tonight, but there’s something I need to tell you.”

“I hope you’re not telling me you have a boyfriend,” I responded, deciding to wait and see what the message was. I would be too tempted to read what she said on my way home.

“No, nothing like that.”

“Okay. What is it?” I asked.

What followed was a very long message explaining that she was Trans (MtF), hasn’t had any reassignment surgery (and wasn’t planning to get any), and that she really liked me and thought I should know sooner rather than later. She also said that she’d understand if I ghosted her after that. I told her that it didn’t matter to me, I’m experienced with both sets of equipment, and that I really liked her too.

“I wish I told you before you left then ;)”

“I’m still in the parking lot,” I sent back.

SEXY TIME

“Come to the door.”

I got out of my car again and went to the door of the apartment building. She was already there waiting for me. She had been texting from the couch in the lobby. When I got to the door she opened it. I embraced her and kissed her deeply again. Her arms fell over my shoulders and mine around her waist. I pulled her close and, for the first time, could feel the slight bulge under her dress pressing against my own. When the kiss broke her mouth brushed up to my ear.

“Come to my room,” she whispered. I followed her as she led the way. When we got in the door I saw her roommate watching TV. I waved briefly as Claire dragged me through the living room off to her bedroom.

As soon as the door was closed behind us I pulled her in tight again and started to kiss her. She began go grind her hips against mine. I ran one hand up through her hair, pulling her face even closer to mine, my other hand trailed down her back and cupped her ass.

We stood there kissing for quite some time before she pulled away and sat down on her bed and looked up at me. I moved closer, leaned forward, and kissed her again. I felt her fingers slide down my chest, over the waist of my pants, then start to trace the outline of my hard cock. Her other hand joined the first and they both made their way to my button and fly, undoing them both. She slid her hand inside my pants and under my boxers and began to gently rub me as we continued to kiss.

She started to tug at my waistband, working my pants over my hips and pulling them to the floor. My boxers were held down at the front by her wrist. As the restriction on my cock was gone, she let it spring out, pulled my boxers down, and gripped me in her hand. The kiss broke and she gazed into my eyes while stroking my cock. She but her bottom lip gently and looked down at her new plaything for the first time. She licked her lips, pulled me closer, and began licking the tip of my cock while still stroking it. She pressed it though her lips and her hand released my shaft as I slid further into her mouth. Her now free hand began to cup my balls, squeezing just enough to be pleasurable but not enough to hurt. I pushed my fingers into her beautiful blonde hair and ran them through until my palms were on the top of her head. She leaned back, the head of my cock resting gently on her ruby red lips and her eyes looking straight up into mine. She held the look for a few long moments before lowering her eyes, smiling nervously, and slipping my cock back into her mouth. My hands rested on her head, but let her set her own pace. I let out a slight moan as I felt her tongue working it’s way around my cock while she continued to bob her head. I wanted to cum so bad, I probably could have, but I wasn’t ready yet. We had just got started. I back up a step and she let my cock fall out of her mouth. She put on a outing face for a moment then lightened her grip on my balls, letting them too fall from her grip.

I leaned in again and kissed her while my hands made their way to the shoulder strap of her dress, slipping them over her shoulders. I moved my head away and she wiggles her shoulders just enough to let the top of her dress fall to her waist revealing her breasts. They were perky and round, her nipples erect and aching for attention. I grabbed ahold of one, manipulating her nipple with my fingers and began to suck on the other. She moaned loudly. Her breathing got heavier, her hands moved up the back of my shirt and rested on my back. I moved my mouth to the other side, light nibbles and a flicking tongue caused her to moan again.

My hand moved to her knee and slowly slid up her inner thigh. She was panting with anticipation. I slowly slid further and further up. My hand grazed her balls as I found the top of her thigh. I very lightly dragged my fingers along her balls, up her shaft, and over the head of her cock. Her fingers curled and her nails began to dig into my back. I wrapped my ah d around her cock and began to stroke it while still nibbling on her nipple. Her fingernails dragged down my back causing a perfect mix of pleasure and pain. I didn’t stay at it for long. As soon as I released her from my grip I grabbed her dress and she maneuvered so I could pull it right off.

I admired the view. Her nipples were wet from my saliva, there was a look of ecstasy and shyness on her face, her hair was messy, and her cock was at full attention. She was roughly average in size and completely hairless. Her foreskin covered the head entirely with a clean of precum at the opening. I kicked off my pants and boxers which were now resting on the floor anyway and quickly peeled off my shirt. We each had a full view of each other’s naked bodies.

I moved closer again and kissed her. She slid further up the bed and I followed. We continued to kiss as I positioned my body on top of hers, slowly lowering myself until we touched. Her breasts pressed against my chest and her hard cock throbbed against mine. My hands made their way through her hair again while hers continued to drag scratch marks down my back. I lifted my hips slightly and her one of her hand moved immediately for the opening, squirming between us, and found it’s way to our cocks. She grabbed her own and began to rub it all over mine before wrapping her hand around both at the same time. She stroked us both slowly at first and progressively getting quicker. I kissed her deeper and her moans were muffled by our duelling tongues. I could feel her precum leaking onto my shaft while my own spread across our stomachs.

I moved my mouth from hers and nibbled on her earlobes, then kissed down the naps of her neck, over he shoulder blade, and onto her breast. I have it a quick tease on my way by before continuing down along her stomach, hip bone, avoiding her cock, and moving to her thigh before working my way back up the inside. My tongue tickled her balls before I took them into my mouth, sucking on them and massaging them with my tongue. She moaned lightly. I popped them out one at a time and ran my tongue up the length of her cock and along the tip. I could taste her precum now. I grabbed her shaft in my hand and slipped my tongue under her foreskin, running it in circles around the edge. She moaned even louder. I opened my mouth and buried her cock as far as I could into my throat before gripping what was left and rolling her foreskin back over her head. She continued to moan. I moved my head up and down in a slow rhythmic motion. Her hands gripped my head and encouraged me to go faster. I resisted and kept a steady pace. She was squirming, aching for more pleasure. I kept her cock in my mouth and began to spin my body until my cock was hanging over her face. She used her tongue to point my cock at her mouth before sliding her warm moist mouth around my cock. We stayed there for a while, sucking each other at the same time. I room her out of my mouth and used my hand to roll her foreskin back and forth. Covered, then exposed, then again. Her moaning continued, muffled by my cock in her mouth.

I heard her mumble something, but couldn’t tell what it was. I slipped her cock back into my mouth and began blowing her quicker than before.

She quickly pulled my cock out of her mouth and yelled out, “I’m going to cum!” louder than I expected.

“Mmhmm,” was all I could manage. Her moans erupted through the room as she came into my mouth. Not large spurts, but more of a dribble. I kept sucking on her until I milked out every last drop. She squirmed even more.

“Oh god,” she said, “I wasn’t expecting that.”

I let her softening cock fall from my mouth as I swallowed the left overs and moved moved beside her to kiss her again. My cock was raging now. I kissed her while playing with her breasts and she gently teased my cock. After a few moments she rolled over, grabbed a bottle of lube from her drawer and applied a liberal amount to my cock. It felt cold and was a bit of a shock at first, but it quickly warmed up.

“Your turn,” she said. She got up and straddled my chest, inching backwards. As my cock started to press against her ass she grabbed me to guide it in, maneuvering herself so my head was pressed against her hole. She squatted down and I felt myself push inside of her. It was warm and tight. She began to bounce on my cock, staring into my eyes. I watched as her breasts bounced and her flaccid cock flopped around with each bounce. I caught the rhythm and thrusted along with her. It wasn’t long before her cock was getting hard. It started bouncing off of my stomach and moved to bouncing off of hers as it grew. She was moaning and telling me how good it felt. After all the build up I wasn’t going to last too long. I reached out and began to play with her cock, caressing her balls and stroking her shaft. She bit her lower lip again and threw her head back crying out with pleasure. I told her to slow down just as my cock started to throb and I unloaded inside of her. She was tight and I could feel my cock pulsing against its restraint. I let out a loud moan as I kept cumming and cumming inside of her.

As my orgasm ended she lifted herself off, but stayed straddling my stomach. I could feel my cum leaking out onto my soft cock. I continued to jerk her off for a few minutes before I went back to playing with her breasts. She took over and began to rapidly jerk off, still looking deep into my eyes. She tensed up, closed her eyes tight, and dribbled a tiny bit of cum out and onto my chest. She was panting now and collapsed onto me. When she rolled off a string of her cum stuck to each of us before finally pulling away.

She got out a rag so we could clean up the worst of the mess. I spent the night. We showered together in the morning, swapping blow jobs in the shower. Then I got dressed and ready to head out.

Her roommate was in the living room watching TV again. “Sounded like a fun night,” she said and winked at me as Claire and I left the apartment so she could see me to the door.

In the end Claire and I dated for nearly a year before she got a job she couldn’t turn down across the country. If this is well received I might write up the story of the night her roommate joined us.