A Cute Tranny

I was feeling lonely at the bar and a woman approached me and had a nice surprise for me.

Sitting a bar one particular night feeling sorry for myself. I must’ve been 4 or 5 beers into the night, no one had said a word to me and I hadn’t said anything to anyone outside of the bartender.

The bar wasn’t busy by any means but it had a few groups of people being loud and obnoxious. The group closest to me seemed to be regulars because they knew the bartender’s name and he seemed to know them as well.

I had just finished off the last drops of beer in my glass and was attempting to get the bartenders attention when out of the corner of my eye, I saw someone sit at the stool next to me. As I turned to look, I noticed that there was an incredibly cute, petite woman in her mid 20’s. She smiled at me and waved her hand to the bartender, who immediately turned his attention to her. She ordered herself a drink and then told the bartender to get me another beer.

“I appreciate that, thanks. What was that for?” I asked

“You looked like you could use a friend.” She responded just as the bartender handed me my beer.

As I said, the bar wasn’t packed and there were plenty of spots to sit so I was excited about the much younger woman sitting next to me, buying me beers all of the sudden.

Still a bit skeptical of why a beautiful woman in her early twenties would sit down next to a burly man in his mid forties, I began to carefully question her motives. As we continued to talk over the course of 4 or 5 more drinks, it became noticeable that she was definitely into me.

Her name was Emma. She was petite, rather flat chested with long red hair, pale skin and an adorable face covered with freckles. She had a tank top on and a black skirt that came down to her knees. She was also wearing a pair of knee high boots. Her aesthetic was incredibly sexy.

It was getting close to closing time and we both decided it was time to leave. I paid the remainder of our tabs and we headed out to the parking lot. It was a really nice summer night and we just ended up talking in the parking lot for about a half hour periodically watching other patrons get in their cars and drive home. We found ourselves the last few people there.

“So… are you gonna make a move or not?” Emma bluntly asked

“I’m working on it.” I said with a laugh

“What more is there to work on? I’m practically throwing myself at you.” laughing as well.

I finally leaned in and gave her a kiss. It was quick but nice. Her lips were thin but very soft. I didn’t wait for a response before I leaned in and kissed her again. This time was much less of a peck and more of a full kiss. I was just about to pull away to gauge her reaction when she opened her mouth and slid her tongue inside my mouth.

When we finally came up for air, it was clear we were both very turned on. Her plan was to Uber home but I told her to cancel it and I would drive her home.

She lived in an apartment about 5 minutes away from the bar so it was an easy drive. When we got to her apartment door, instead of unlocking the door, she turned to me with a concerned look on her face. I thought she was having second thoughts and backed up a step or two. It was obvious she had something to say.

“What’s up?” I asked

“Um.. (sigh) You know I’m trans right?” She said with a look of worry on her face

“What?” I asked

Honestly I was shocked. Not because she was transgender but because I just spent a couple hours with her, we made out in the bar parking lot and I honestly didn’t know. Being bisexual it was no concern to me whatsoever, but it felt like I was expecting a fastball and she threw me a curveball.

“Yeah.. I have a penis.” She confessed looking a bit disappointed

I closed the small gap between us and started kissing her again. She immediately stopped me.

“You’re ok with this?” She asked

“I honestly didn’t know but I’m bisexual so it’s not remotely a problem.” I explained kissing her

Emma exhaled a sigh of relief, smiled and turned to unlock her door. It took her less than two seconds to do that but in those two seconds I was able to readjust my mindset. I was expecting to have sex with a biological woman and now was recalibrating for a trans woman.

I had an erection since we left the bar so in an effort to show her I was still very much into her, before she opened the door, I got behind her as close as I could so she could feel it. I put my hands on her hips and kissed her shoulder and then up the back of her neck. My hand slowly reached around and found she had an erection now as well. She quickly brushed my hand away with a giggle and opened her door.

We sat on her couch and she brought a couple more drinks for us. We talked for a few more minutes, mostly about our sexuality, mine in particular. Kissed a few times. Drank our beers.

Emma laid back on her couch and signaled for me to get on top of her. I pounded down the rest of my beer and climbed for it. She hiked up her skirt and I got a quick glance at her dick just peeking out from her panties. She wrapped her legs around me and we began making out rather aggressively.

“Let’s go!” Emma said as she pushed me off her, stood up and grabbed my hand.

She lead me to her bedroom where we immediately began kissing again. I reached around her and unzipped her skirt. As it fell to the floor she kicked it off and lifted her tank top and bra off. She had to most adorable little tits. Puffy soft pink nipples perfect for sucking.

Emma sat on the edge of her bed and started undoing my pants. She gave a good tug and pulled them down to my knees. I removed all my clothing as quickly as I could from there. She reached out and grabbed the base of my shaft with her cold hand. How she had cold hands in the middle of August I’ll never know but it felt amazing on my hot blooded cock.

She began sucking the tip of my dick. Her warm breath mixed with her cold hand was enough to make me explode right there! I managed to contain myself and let her do her thing. I went to the bar that night to unwind and forget about the bullshit I was dealing with at work and at home and she was quickly making me forget everything.

I knew if I let her continue I was going to explode and I wanted this to last a little longer than 30 seconds. So, I pulled away and got on my knees. I pulled her panties down and threw them in the mixed pile of clothes we left on the floor. Her cock was as adorable as her puffy little tits. No bigger than 5”.

I opened my mouth and put her little she cock in. My hand began to play with her balls. She let out a sigh of relief that almost matched mine and she fell back on her bed. Within a minute she put her hand on the back of my head and began grinding along with my head bobs. I felt a warm shot of cum hit the back of my throat, followed by a second and third. I did my best to swallow and keep sucking at the same time.

“Holy shit that felt good!” She said sounding like a weight had been lifted from her shoulders

Emma reached for a drawer beside her bed and pulled out some lube and a condom. She handed them to me looking unsure if I wanted to take them but I eagerly snatched them from her hand.

I put the condom on and lubed everything up. I got on top of her in the missionary position. She lifted her legs up exposing her cute little ass and I pressed my cock against her hole. As the tip of my dick pressed forward she bit her lip and moaned softly. When the entire head of my cock popped inside her, she yelped a bit and put her hand on my thigh almost like to tell me to go slow. I knew what I was doing though. I had been in her position many times before.

Slowly I began pushing my throbbing cock in and out of her petite little body. Each time going a bit deeper. When she finally relaxed completely, I could slide in and out of her with ease. She was so petite and small that when I looked down at her stomach, I could see where my cock was thrusting inside her. I knew I wasn’t going to last much longer. I quickened my pace and began thrusting as hard as I could.

“I’m gonna cum!” I grunted

With one final thrust I could feel my balls emptying into that condom. I got lightheaded. My toes curled and my legs began uncontrollably shaking and I released my hot cum.

When I finished shaking and I calmed down, I pulled myself out of her and laid next to her. We were both sweating now and struggling to catch our breath. We both laid silent for a minute or so.

“You have a big dick.” Emma said still gasping slightly

“Thanks.” I answered

We both laid naked for about 20 minutes talking and whatnot. I remembered how much I loved her little puffy tits and how I hadn’t played with them at all yet. So I casually began touching her stomach and seeing if she might be coerced into another round.

As my hands eventually made their way to her little titties, she didn’t stop me. I carefully massaged them and gently pinched her nipples. She giggled a bit. I leaned in and started licking and sucking on one. It was perfect!

“Are you still horny?” She asked

“Mhmm.” I muttered barely letting go of her pink nipple with my lips

“There’s more condoms in the drawer.” She mentioned

I quickly rolled over and grabbed another condom.

“How do you want me?” She asked

I rolled her on her side, spooned her from behind and slid my cock back inside her. This time I lasted much longer! I was able to enjoy her from a a few different positions before I inevitably orgasmed.

She let me stay the night with her where we slept naked together. The following morning we awoke, and after fondling each other for a few minutes, we exchanged blow jobs then went out for breakfast.

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