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As I laid there on the bed, slowly waking up from last night’s excursions, my mind was still wildly active. I guess I was only able to sleep from sheer exhaustion because I soon as I awoke, I was still
I’m utter disbelief of the night I’d just had. I had never had an attraction to or anticipated myself having any sexual interactions with a trans person before but last night was one of the most pleasure-filled and exhilarating nights of my life! I could wait to talk to Jennifer when she woke up.

Wait…..where was she??

I turned over on the hotel bed and didn’t see Jennifer anywhere. I listened for a moment to try and see if I had heard her in the bathroom, but there was nothing. She was gone….

I sullenly sat up on the bed, still naked, my cock resting on my thigh, soft and defeated.

*she couldn’t have even said goodbye? I wondered we had really connected….* I wondered to myself.

As I got off the bed to go to the bathroom, I realized that the bathroom light was still on. When I opened the door, there was a note attached to the bathroom mirror. It read:

“Jack, sorry to have run out without saying bye! I had a great time last night. If you’re in town for a few more days, call me!! Xoxo, Jenny”

Her phone number was listed just below the note with a heart as well. It subsequently made my heart jump for joy. She didn’t just leave me hanging as a one night stand!

I fist pumped by myself in the bathroom out of sheer excitement. I wanted to call her right then, but figured I would give her some time to maybe sleep off the night before. I had a full day of work conferences to attend anyway so I wouldn’t be super available until later. With the excitement still lingering, I got into the shower to get ready, my cock tingling with anticipation of the next time I would see Jennifer.

The remainder of my day, I could barely focus on anything but Jennifer. The images of her shooting cum onto herself as I fucked her ass was the hottest thing I’ve ever seen, and felt. I was still questioning a lot of what I was feeling, but the lust for more was obviously there. I couldn’t wait to message her.

When my day was finally over, I rushed back to my room, trying to understand the best message to send. I sat down on my bed and began typing before I finally sent what I wondered was a good message to let her know I wanted to see her again.

“Hey Jennifer, it’s Jack. I thought you left me hanging when I woke up without you but was ecstatic to see the note you left! I would really like to see you again whenever you’re free, I’m in town until Saturday!” (It was Thursday).

I waited for what seemed like an eternity but what was really only about 20 minutes or so before Jennifer texted me back.

“It’s about time you got back to me!! Are you free tonight?”

I was so happy to see that she was still interested and hadn’t wondered better of her decision while waiting for me to message her. I immediately texted her back that I was free and looking forward to it. We agreed on a mutual place that wasn’t too dressy and shouldn’t be too crowded, a good place to enjoy dinner and each other’s time. I jumped back in the shower and got ready to meet her before heading out the door.

I got to the bar that we agreed to meet at first. I’ve all the time liked being early, it helped me ease my anxiety. I could imagine scenarios to try and be as ready as feasible for any curveballs I might encounter. It sounds silly but it works for me.

I sat at the bar and ordered a drink when I heard the ringing of the door as it opened. I turned to see Jennifer walking in. She was wearing skin tight jeans, white shoes that looked like Vans, and a tight long sleeve gray shirt that really accentuated her chest nicely. Her hair was straightened and shined nicely with the lighting. Drop dead beautiful.

“Hey Jenny, over here!” I said as I waved my hand to get her attention. She noticed me, smiled, and walked over to sit down. She took a seat next to me at the bar and crossed her legs. I told the bartender to put her drinks on my tab, which Jennifer thanked me for.

We started off with the usual how’s it going and whatnot, general chit chat. Asked about each other’s backgrounds and things like that. After a few drinks, our conversation became a little more frisky.

“Listen, those jeans are tight as hell, which I love. Your ass looks amazing. But I gotta ask, how are you hiding it?” I asked, alluding to how she was able to fit her cock in her jeans without a noticeable bulge.

Jennifer belly laughed. “I guess you learn a few tuck tricks over the years!” She responded. “I was waiting for you to say something after seeing how you were looking at it last night.” She said with a wink.

“Well it’s not everyday you see one that big!” I said. “And it’s definitely not everyday you get to suck one!”

Jennifer laughed at my brashness, but she appeared to really like that I was open minded and free to say whatever came to mind. It was helping me mentally weave my way through all of these new experiences.

“So what did you mean by what you said last night before we fell asleep? ‘Maybe I can try you on next time?’” I asked Jennifer.

It took her a minute to respond.

“I just meant, and I know you’re still really new to all of this and I don’t want to push things too far, but if you wanted to try, I could be the one fucking you next time?” She said.

I was surprised at the proposition, but really intrigued at the same time. I had already tried and really loved one new thing so far this week, what’s the problem with trying another?

“Yeah I guess we could try that! No promises though, I have no clue what I’d feel once we start. You’d have to walk me through it!”

“Don’t worry, I can be gentle if I need to be,” she said as she put her hand on my arm.

We changed the subject for a while before returning to similar topics near the end of the night.

“So if I was going to let you fuck me, I imagine there’s a few things I’d have to do beforehand to clean myself up, right?” I asked Jennifer.

“Oh yeah, you definitely have to…uh…do your business to clean yourself out. And then honestly use a douche to get the rest of everything out before we’d want to get started.” She responded.

“Yeah makes sense, all good things to know. I’ve been thinking about it since you mentioned it and I honestly think I’d like to give it a try!” I said.

Jennifer smiled a gigantic grin and laughed excitedly, anticipating what was to come.

“I swear I’ll go easy, but you’re gonna love it I promise!” Jennifer said.

We continued talking about what I’d should do to prepare and then decided we could get back together at my hotel tomorrow night. As we got ready to leave, I opened the door for her and she exited ahead of me, her ass swinging side to side in a hypnotic motion. She turned to me as we said our goodbyes and we kissed deeply before she got into her car. I could feel her pushing against me, my cock hardening slightly and the feeling of a slight bulge in her jeans as well.

“Can’t wait for tomorrow!“ she said through her open window as she drove off.

The next day, I ran out to the store to get some “equipment” to help myself get cleaned out and prepared for losing my anal virginity. With a few supportive and informative texts from Jennifer, I was able to get myself properly prepared for what was to come later that night. Finally, the time was here, and Jennifer was on her way over to my hotel room.

*knock knock knock*

I hurried to the door to see Jennifer standing there in a white athletic sweat outfit, looking amazing as all the time. I welcomed her into the room and she set her stuff down on the nightstand. We talked for a while and had a couple drinks to loosen ourselves up a bit. Finally the time came where we were both ready to get down to company.

“So are you ready for the best experience of your life?” Jennifer asked me.

“You can’t even imagine how nervous and excited I am!” I replied.

“Once we start, make sure you let me know if I’m going to quickly, I don’t want to ruin anything for you!” She reassured me.

We both stood at the foot of the bed and embraced one another, kissing each other with a fiery passion. I could feel Jennifer’s dick getting hard in her sweatpants. In a break from our kissing, I quickly glanced down to see her protruding against her pants, a noticeable bulge waiting for me to unleash it. I decided to surprise Jennifer and make the first move.

I knelt down in front of her and slowly began pulling down her pants and underwear together. I looked up before completely unleashing her monster, seeing her excited look as she bit the corner of her lip. I looked back to what I was doing to see the base of her cock, swollen and pointed downwards, still trapped in her pants. I continued to pull it down until her entire nearly 10” cock was staring me in the face. I could feel my own manhood springing to life in my pants as well. Her head was throbbing already, anticipating the virginity it was gonna take.

I opened my mouth and grabbed ahold of the base of her dick as I slid the tip in. I flicked my tongue along the bottom of her cock, feeling her twitch slightly as I did so. She moaned as I began to bob my head forward and backward, taking as much of her in as I could with each gulp.

It wasn’t long before I could feel her cock ramming into the back of my throat. Thankfully I had a depressed gag reflex and although I couldn’t quite deepthroat, I was able to fit a healthy amount into my mouth. I felt the saliva dripping down my chin as I sucked her cock, begging her to feed me more and more of it. I looked up momentarily to see that Jennifer was removed her shirt and was standing naked, her hands pinching her nipples as I sucked her.

I continued for what seemed like a couple minutes before I felt Jennifer’s hands grab my chin, releasing her cock from my mouth. She pulled me upwards and embraced me again, this time reach down and sliding my pants down, letting my semi-hard cock flop out towards her. She grabbed it and started to stroke it gently before reaching around with her other hand and beginning to play with my ass. She inched her way closer and closer to my asshole, slowly prying me open. Eventually I felt the pressure of her finger prodding against my ass, pushing slightly but not enough to enter me. She was probably just imagining what I had to offer her.

A few more minutes passed and we broke free from our embrace, standing and facing one another awkwardly for a moment.

“I don’t think I can wait much longer…” Jennifer said in anxious anticipation.

“I’m as ready as I’ll ever be!” I responded.

I laid back on the bed on my back, unsure of what was to come next. Jennifer quickly went to the nightstand and grabbed her bottle of lube from her purse.

“I’ll make sure I use a lot!” She said.

She approached me and stood between my legs. She grabbed both of my knees and pulled them upwards so that my ass was the closest thing to her, the standard missionary position. I watched as she squeezed a healthy portion of lube onto her hand and reach down to massage my asshole. I felt the pressure of her fingers and she applied the lube to my opening. She played with it for a moment before slowly beginning to insert one of her fingers. I felt the pressure but was accepting her into me easily.

“Are you okay so far?” She asked.

“Yeah I think so! Keep going,” I responded.

“If it ever feels too much, try to relax and push outward, sometimes that works for me.” She said.

As soon as she said so, I felt the presence of another finger enter me. The pressure intensified but still wasn’t too much for me to handle. The feeling was very new but I was enjoying it, as was my cock by the looks of things. I peeked down to see I was already leaking precum even though I was only partially hard. I felt her curl her fingers inside of my asshole, as if she was attempting to control my cock like a puppet. I moaned quietly as I began to enjoy the new pressures.

This must have excited Jennifer as she pushed in yet another finger.

“Okay that’s 3!” She said. “You’re doing great.”

We continued with the finger play for a few more minutes before Jennifer couldn’t wait any longer. She removed her fingers and grabbed ahold of her cock as she stood facing me.

“Just for fun, here’s how far into you I’ll be,” she said as she laid her hard cock along my stomach. She reached up past my belly button which was both exciting and terrifying at the same time.

“Give me that cock…” I said to entice her even more.

Jennifer grabbed the lube again and squirted a very healthy amount all over her cock, making it glisten with the light in the room. She knelt down slightly and pointed it towards my asshole. She bit her lip as she prodded against me.

The pressure started slowly and mounted very quickly. I felt Jennifer slowly pushing against my ass as I attempted to push outward to allow her easier access. Suddenly I felt her cock enter my asshole. The pressure was much more than her fingers but I tried to relax as much as I could. I could feel her sliding in deeper, probably 2-3” at first. She stopped to check if I was okay before proceeding. As she moved forward, I could feel the pressure moving from my asshole to deeper inside of me. I moaned loudly as she continues to penetrate me.

Soon she started to thrust slightly, entering me more with each thrust. She kept eye contact with me to make sure I was okay, but I could see she was struggling to hold back her own pleasure of knowing she was taking my anal virginity. The pressure continued to mount before I suddenly felt something else hit my ass. I looked down to see that Jennifer was completely inside of me, I was feeling her balls touch my ass, reaching their final destination. I looked up surprised at Jennifer, who looked at me and simply smiled.

“I told you that you’d love it..” she said seductively.

“Keep going, please!” I moaned.

This sparked a reinvigoration of Jennifer as she quickly picked up the pace. She began to thrust more quickly and I could feel her balls slapping my ass as she fucked me. I begged her to fuck me and make me cum, which only quickened the pace. She was fucking me lifeless and I was lying there doing my best to take it all in. After a couple minutes I felt a sensation in what I wondered was my bladder, almost like I had to pee, but it was intensifying rapidly. The feeling lingered for another 30-40 seconds before I looked down to see that I was fully hard and my cock was standing straight up, flopping with each thrust from Jennifer.

Suddenly, it erupted. I began to cum and felt the most intense orgasm of my life. With each thrust from Jennifer I shot more cum into the air as it arched back onto me, covering my chest with my own cum. Jennifer smiled as she watched me have a hands-free orgasm, obviously my first. She continues to pound me with intensity as the ropes of cum began to slow, my cock very slowly beginning to soften. My moans slowed as the feelings began to subside.

It wasn’t long before I heard Jennifer’s moans increase. She was also about to cum and I saw that her jaw was tensing with her upcoming orgasm.

“Cum in my mouth!” I said quickly.

This startled Jennifer for a split second before I felt her remove her long thick cock from my ass, leaving me gaped. I quickly repositioned my head towards the base of the bed with my mouth open, awaiting her sweet juices.

She stuck the head of her cock into my mouth and I quickly felt a warm spray of cum down my throat. I gulped to try and make more room as the cum kept on filling my cheeks, pumping her seed deep into my mouth. Jennifer moaned as I grabbed her cock myself and began to stroke her towards me, milking every ounce I could get. I had turned cum hungry and wanted more and more of what I worked for.

After a few moments I felt Jennifer’s cock beginning to soften, her orgasm completed. I opened my eyes to see her panting, staring and smiling at me. I removed her cock from my mouth and smiled back.

“So….do you think you’re a bottom now?” She said jokingly.

I laughed, thinking to myself that I most definitely was.

“I think you honestly just changed my life,” I responded.

We laughed and Jennifer laid down beside me, both of us exhausted from the intense fuck.

“So when’s round 3?” I asked…….

NSFW: yes

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