First Trans Experience [M30/T24] [First Time] [Anal]

I was sitting at the hotel bar enjoying a beer, wasting some time before heading back to my room for the night. I was out of town for a work conference and since I was the only person from my company who went, I didn’t really have anyone to hang out with at the hotel, so I was drinking alone.

The bar was a pretty popular spot in town it seemed like, not like a normal hotel bar with a few stragglers hanging around. This place had live music, packed dance floor, a really good environment to hang out in for a little bit.

As I sat and enjoyed my drink, I noticed a group of girls walk into the bar, appearing to celebrate some sort of bachelorette party. They had on the usual sashes with all of their nicknames and catchy phrases written on them, dressed skimpily to boot. The bride-to-be was obviously over-served already but still seemed to have her senses about her. About 8-9 of them made their way through the door and towards the bar.

One of the sashes ended up catching my eye. I had to read it 3-4 times to really make sure I was reading it right. Her sash said “The One with the Big Dick.”

Huh?

*well good for her boyfriend* I thought to myself, thinking it was alluding to her significant other having a big package.

They all gathered around the bar and ordered their drinks. Being that I had a few already and was feeling generous, I told the bartender to put their drinks on my tab, hoping they’d be able to enjoy the night a little longer.

Once he spread the word to them, they had the usual uproar and all headed over my way to thank me.

“Thank you so much! You’re the best! We love you!” They said basically all at once. I tipped my glass to them and told them to have fun and congratulations on the exciting news.

“Before you go though, tell me what all of your sashes mean!” I said.

They laughed and started to rattle off the funny stories revealing the meaning behind the clever names. Finally it came down to the one I was most interested in.

“Well, I have a big dick, so that’s why I’m the One with the Big Dick!” She said.

“So like your boyfriend has a big dick or is a big dick or something?” I asked inquisitively.

“No….I have a big dick!”

I sat there with a confused look on my face, still not getting the point. “I don’t get it!” I said.

They all laughed as she picked up her skirt. She was wearing a black tank top, white skirt, and nude-ish leggings that seemed to really match her darker complexion which I assumed was of Latina descent. Her dark hair was shoulder length with a perky chest, probably C cup and she stood about 5’7” tall.

As she lifted her skirt, I saw the noticeable bulge between her legs, and my jaw dropped open.

“Oh now I get it!” I said as I laughed out loud. “Yeah the nickname fits for sure!”

They all continued to laugh and she did as well, blushing a bit. “Maybe if you play your cards right you can see it for real!” She said as she winked.

I was a recently divorced guy who was still trying to figure out the single life. I had never before had any attraction to anyone other than a woman but was finding myself surprisingly aroused by her proposition.

“We’ll see where the night goes!” I said as I tipped my glass again. With that, they headed back towards the dance floor, but not before she waved bye to me playfully one last time.

As I sat and continued to have a drink, I couldn’t stop thinking about the unreal situation I was just in. I was really caught by surprise and found myself staring at the dance floor, watching her dance. I didn’t even get her name! I was hoping she would come back over before the end of the night.

Luckily for me, she did. Just after midnight, the whole group came over for another round of drinks. *I’ve gotta get her name before she leaves* I thought.

I decided to buy another round for them. They were all feeling a little more tipsy and were definitely more playful this time around, all hugging me and kissing me on the cheek after I bought them the drinks.

After things cooled down a couple minutes later, I was happy to see that she was walking over to me, taking a seat next to me at the bar.

“So, have you thought any more about my offer?” She said playfully, touching my arm as she laughed.

I instantly felt my dick jump in my pants which aroused and confused me at the same time. “I don’t even know your name yet! Aren’t we moving a little fast?” I said.

“I’m Jennifer, very nice to meet you,” she said as she stuck her hand out for a hand shake.

“Jack, the pleasure is all mine!” I said as we jokingly shook hands enthusiastically.

“Not just yours,” she said again playfully, sticking her tongue out and laughing.

We sat and talked for a few more minutes before her friends started to gather their things to leave. “Aww, I was really having fun talking to you! I don’t want to leave yet.” Jennifer said.

“I’m staying at the hotel so I’ll be here for a little while longer if you wanted to stay for another drink,” I offered.

She hurried over to grab her things and brought them back to the bar before she said goodbye to her friends. As she came back over, she took off her sash and put it in her purse.

“So, Jack. On a scale of 1-10, how surprised were you by my big secret?” She said, obviously referring to her above average penis.

“Jennifer, I’ve gotta be honest, 10. I would have never guessed that you were trans. I mean you’re drop dead gorgeous!”

Jennifer blushed at the compliment, reaching over to graze my thigh.

“How big is it if you don’t mind me asking?” I said.

Jennifer laughed at the straight forward question. “That’s something you’ll just have to find out for yourself!” She said seductively.

I could feel my manhood starting to grow in my jeans as I reached my hand down to try and adjust myself. I saw Jennifer’s eyes shoot downward as I did so.

“Sooooo…..are the rooms nice here?” Jennifer asked.

I couldn’t tell if she was trying to get me to ask her to come to my room or if she was just trying to continue the conversation. I decided to try and take advantage of the perceived opportunity.

“Yeah they’re really nice! Do you want to see them?” I asked.

Jennifer perked up quickly as she accepted the invitation. I paid the tab at the bar and we headed to the elevator. Jennifer was walking in front of me, her toned ass swinging beautifully behind her. I could feel myself throbbing again, still unsure of the situation but just trying to enjoy the moment.

We entered the elevator and I hit the button for floor 10. The doors began to close and I could feel Jennifer nudging closer to me. I looked over at her and she was staring at me, biting her lip and playing with her skirt. Feeling compelled to do so, Ieaned down and kissed her deeply, wrapping my arm around her waist and pulling her closer to me. I could feel her kissing me back, embracing me with equal force. I moved my hand downward as we kissed, running my hand under her skirt and squeezing her toned ass, feeling her push even closer to me. As she did so, I could feel her bulge getting slightly bigger against my thigh, sending my mind on a frenzy of sensations.

*is this really going to happen?* I thought to myself.

We both heard the ding of the elevator and released our embrace as we walked out the door. I grabbed Jennifer’s hand and led her to my room where I quickly opened the door and let us inside. She set her stuff down on the night stand and we both kicked off our shoes, ready to continue what we started in the elevator.

“So before we keep going, I’ve gotta ask,” Jennifer said. “Have you ever done anything like this before, been with a trans person?”

“Honestly no, I’ve never even envisioned it. I’ve been completely blown away by you all night though, it feels like this is the right thing to do as long as you’re okay with it too.” I said back.

Jennifer smiled, “okay, as long as you’re sure! And if you ever want to stop just tell me, I know it’s going to be a different experience for you!”

Without waiting any longer, we both embraced each other again, kissing one another deeply. Her hands ran down my chest as I groped her ass, feeling her bulge get bigger by the second. Mine was growing as well and I knew she could feel it in my jeans.

I started to unbutton my shirt and before I could even get halfway down, Jennifer grabbed ahold of it and ripped it open, tearing it off me to reveal my toned but not overly fit midsection. I was on the hairier side and she slowly traced her finger down my chest, playing with my chest hair as she did so.

She slowly made her way downward and I let her see the pace, standing to wait for what was next. She eventually made it down to my belt buckle, my cock just below it attempting to bust its way through my zipper. She slowly undid the belt buckle and the buckle on my pants before grabbing ahold of the zipper. Before she moved forward, she looked up at me and kissed me again, and began to unzip my jeans as she did so.

Once completely open, I could feel my cock throbbing uncontrollably, pulsating in anticipation. Jennifer broke free from our embrace and knelt down in front of me, slowing pulling down my pants and underwear. My cock shot straight outwards towards her face once she finally got them off. I was rock hard, 8” staring directly at Jennifer.

Her expression let me know she was pleased with what I had for her. She smiled seductively at me and immediately wrapped her hand around my dick as she took in the first 4” with ease down her throat. I almost dropped to my knees when she started to gently twist her hand as she bobbed her head back and forth on my cock. Her tongue was darting around the head of my manhood continuously as she slowly took more and more of me down her throat, bobbing her head slightly quicker with each motion.

After a couple minutes Jennifer nearly had my entire cock in her mouth. She was struggling slightly but appeared to be really enjoying it, as was I. I could feel the slight tingles of an oncoming orgasm and knew I wouldn’t last much longer if we continued this way. I reached down and gently pulled her off of me, which was followed by a surprised look on Jennifer’s face.

“I want to make sure I last a bit longer for you, and at this rate I’m gonna cum any second!” I said somewhat jokingly.

Before she could respond, I grabbed the bottom of her shirt and quickly lifted it up over her head. I was surprised to see that she didn’t have a bra on, revealing her perky, beautifully tanned tits. A slight tan line outline could be seen around her breast which I found extremely sexy. Her nipples were hard as rocks as I leaned down to take them into my mouth, playing with them with my tongue as I caressed the other, slowly making my way downward. I switched back and forth a few times as I continued the foreplay, feeling her grab ahold of my dick to make sure I wasn’t missing out.

*well I guess it’s now or never* I thought to myself.

To Jennifer’s surprise, I knelt down in front of her and pulled down her skirt and leggings in one motion. My jaw nearly dropped to the floor when I saw what was waiting for me. Her cock was massive. It was rock hard and throbbing, and had to at least be 10” long and decently thick. It was dark as was her Latina complexion. As it was erect, it pointed slightly to the left and slightly downward, veins showing its full capacity. Her balls hung just below, glistening slightly.

Jennifer saw the surprise on my face. “Don’t be scared, it won’t bite,” she said seductively. “I told you it was big!”

“Yeah, you were fucking lying! I’ll try my best but I’ve never done this before so just let me know what I need to do better!” I said.

I grabbed ahold of her cock and felt it jump slightly at my touch. I finally got over my fear and decided to try and take as much as I could at once. I opened my mouth and felt her warmness fill the void. I shot my tongue out to try and make more room (which I had heard about from my extensive porn watching) and it actually seemed to work. I was able to take probably 4-5” of her cock but then started to gag slightly. I decided to pull back a bit and focus on the tip of her dick, working my hands along the base. Whatever I was doing seemed yo be working as I could hear Jennifer moaning as I sucked her.

I continued for a few minutes, trying to please her as best I could with my newfound techniques. I could feel the saliva dripping down my chin as I played with her balls.

“Please fuck me…” she said in a whispered seductive tone.

I pulled back and removed her cock from my mouth. As I stood up, we kissed for a moment before Jennifer laid back on the bed. Her legs opened up, revealing her tight asshole and her cock laid on her stomach, reaching up past her bellybutton. She looked amazing.

“Before you start, grab the lube out of my purse, it’s just right inside.”

I walked over and grabbed the lube. I drizzled a healthy amount on my cock and rubbed it all over.

“Don’t forget my ass!” She said laughing.

I drizzled mover over her ass and also her balls, rubbing it all over to cover her completely as she laid there glistening with oil.

I took position in front of her, my cock still throbbing with excitement. Jennifer looked at me with an excited smirk as I prodded the head of my cock against her asshole. I slowly pushed forward, feeling her ass give way slightly. She was extremely tight. I continued to push with slightly more force, watching her expression to judge my next move. She had her eyes closed but seemed to be enjoying the slight penetration.

I pushed a little harder and felt the first couple inches of my cock enter her, accompanied by her joyful moans. Her cock jumped involuntarily as I entered her.

“Mmmm fuck yes, keep going Jack!” Jennifer said.

I continued to thrust, entering her completely, all 8” buried in her ass. Jennifer moaned loudly at the gaping of her asshole, feeling the pleasure of the pressure. I started to thrust more in rhythm now that I was inside of her, feeling her asshole tighten around me. Within minutes I could feel myself working up to an orgasm.

I continued to thrust harder to match the intensity of Jennifer’s moans. Her tits were bouncing as I fucked her, as was her cock. She had slightly lost some of her erection but was still mostly hard, her cock flopping against her stomach with each thrust. It was such a new sight that I wasn’t used to but was extremely sexy. I could see her precum leaking onto her stomach.

“Oh fuck yes, Jack! Keep fucking me harder! Oh fuck yes!” Jennifer exclaimed through her moans.

I picked up the pace to as fast as I could go, watching Jennifer play with her tits. I reached down and started to jerk her cock as I fucked her.

“Cum for me baby…” I said.

“Oh yes keep going, keep going! I’m going to!” Jennifer responded.

As I entered her, I could feel her asshole tighten quickly. Her cock was pulsating and I knew she was about to cum. Suddenly it erupted, spraying ropes of cum up into the air, arcing back down onto her chest. A couple spurts even made it up to her chin, covering her chest completely with cum. She raised her waist as she orgasmed, increasing the intensity of her climax.

I tried to match her intensity as her orgasm began to subside, her breathing and moaning slowing slightly. I couldn’t last any longer. As soon as the last of her cum leaked out, I pulled out and started to shoot my own cum all over her. It shot all over her slowly softening cock and balls, before making its way up to her stomach with each burst. Jennifer laid on the bed breathing heavily as I glazed her completely with my cum. Eventually my orgasm also began to subside as the last of my cum dripped out.

I stood at the foot of the bed, watching Jennifer recover as I did as well, my softening cock in my hand. She laid there catching her breath, slowly coming back to her sense, her hands tracing the cum on her body around her breasts.

She opened her eyes and looked down at me, my cock still in my hand.

“I hope you got it all out because I don’t think I have anywhere else to put it….” Jennifer said as a joke, alluding to her entire body being covered in cum.

I was happy she broke the tension as we both laughed, because my mind was all over the place. This was a completely new experience but felt so fulfilling to me at the same time that I really didn’t know what to think.

“I’m gonna go get cleaned off real quick!” She said as she jumped up to go to the bathroom.

I sat on the bed and felt my cock relaxing between my legs. Jennifer came back out quickly, her big cock swinging between her legs as she strode over to me. She sat beside me on the bed.

“For your first time, that was fucking phenomenal.” She said to me in a serious but upbeat tone.

“I’m happy you think so! It was pretty amazing for me too! I’m still sort of processing the whole thing!” I said as I laughed.

Jennifer understood where I was coming from and put her arms around me, her hands playing with my chest and slowly running downwards to slightly caress my cock.

We laid down on the bed, exhausted and tired.

“Maybe I can try you on for size next time?” Jennifer asked.

Source: reddit.com/r/Erotica/comments/10lu1bn/first_trans_experience_m30t24_first_time_anal