First Experience with a T Girl

I am 29M, and I just turned 29 six months ago. And this happened on my birthday. What a birthday gift!

I am Indian but I've lived in the US for almost 7 years now and recently just moved to California for work a year ago. I was just recently coming to accept the fact that I might be bisexual when this happened.

Since it was my last bday in my 20s before the number 3-0 rolled around, so I wanted to really make sure I go out and have a nice time. So me and a few friends of mine went out to clubs and started drinking and dancing and having good 'ol time. I had decided I wanted to definitely get laid tonight and have myself some nice birthday sex and my friends made sure everyone, every where we went knew that.

Drunk people are great friends. So I had random people buying me shots, drinks and what not. At first I asked them what drink it was but after the a while I stopped and just drank. But I was hydrated, I didn't want whiskey dick ruin my plans for the night.

Out of those people who bought me drinks, there were a few women too. Some just bought me drinks, some wished and came and gave me a kiss on the cheek too, and some really drunk ones twerked on my crotch and left. In short, I was having the time of my life.

And thats when I saw her. She was dancing just a few feet away from me. I thought she was absolutely gorgeous. There were people around close by each other so I couldn't see anything other than her face. She was dancing with her friend and by this time I dont know who I was dancing with or where my friends were. And suddenly we locked eyes when someone wished me happy birthday and brought shots for me.

She looked at me, smiled and I smiled back. A while later the crowd moved and somehow we came nearby each other and when that happened, she wished me, and I said thank you.

"I dont have shots to offer you but I can give you a kiss" she said leaning in.

"I'd love a kiss" I offered my cheek I expected a kiss on the cheeks.

To my surprise, she grabbed my face turned it towards her and just started kissing me.

It wasnt just a peck, she locked her lips with mine. We must have kissed for a few seconds when my tongue made an appearance in her mouth. She broke it, looked at me for a second, then said,

"Okay" and then came back in to kiss me with her tongue.

And suddenly we were vigorously making out in the middle of the dance floor with our hands moving around each others body.

When we broke the kiss to look at each other for a while and to breathe, thats when I looked at her body. It blew my mind. This woman was smoking. The kind of woman I never had any chance with. And here I was making out with one. I couldn't believe my luck

Before she could change her mind, I went in to kiss her again. And she welcomed with open lips and made out with me more. My hands were all around her back, waist, neck and for a little while her plump ass, which was very firm so it definitely looked like she worked out.

I dont remember how long we were making out but suddenly we realised we hit a wall and we were out of the crowd. And as we hit the wall we stopped making out and looked what happened and started laughing that we didnt realise that were out.

Taking that opportunity, I asked, "Want to get out of here?"

She looked at me for a second and then said, "Sure, birthday boy"

So we got into the uber and were out of there. Even in the uber we couldn't stop making out. I couldnt stop grabbing onto that plump ass. It felt so nice to squeeze it.

The moment we stepped into my apartment, she had started taking my clothes off and I pushed her against the wall and started biting her neck and started to unzip her dress. At which point she stopped me for a second and said,

"Are you sure? You might not see what you're expecting"

I was surprised, but I didn't care. I said, "I dont care"

But in my head I said to myself that even if this woman had a dick I would fuck her.

She was wearing a black dress and once I took off its zip, that was it. I first took down enough to reveal her boobs, and to my surprise, she wasnt wearing a bra, just some nipple pads. They sat up straight. They must have been around 34C. Definitely fake, but hey, California, you never know.

I was happy to suck my first fake boobs on my 29th birthday. As i sucked her boobs, she lowered her dress and then took off my pants. And once she took off her dress, I slowly moved one of my hand down towards her crotch. While she caressed my dick through my underwear with one hand and with the other caressed my hair.

As I put my hand on her crotch, I felt a bulge. A bulge that was tucked away but getting thicker. I took her boobs out of my mouth and looked down and then looked at her.

She just looked at me and smiled, I looked at and then where my hand was. A million thought raced in my mind, but one was the most dominant one. I wanted to see it. I wanted to hold it in my hand as she held my hard dick in hers.

I put my hand inside her panties and pulled her almost hard dick out and held it in my hands. I looked at it, and then at her. While looking at her, I took another hand of hers and placed it on my dick. She understood. She started playing with my dick as I started playing with hers.

"You've a beautiful dick", I said to her. It was beautiful. It must have almost been around 6 inches but it was really thick. Her dick was thicker than mine. I am around 8"x3.8". She must have been easily over 4 inches thick.

"Thank you, yours is even more beautiful" She said and started to jack me off.

I started to jack her off in response and we were back making out again. After a while she took me to the couch and at me down.

"Let me give you a proper birthday gift."

Once I sat down on the couch, she spread my legs, kneeled down in front of me, and while tying her hair she said,

"I'm gonna give you a Veronica special. By the way, I'm Veronica"

To which I replied, "I'm Yash"

"Yash!? Sounds a lot like 'Yes'. I like that. Will come in handy later."

And then she went down and in one quick motion took my entire dick in down to her throat. She had no gag reflex. That blew my mind.

For the next 15-20 minutes I had the most mind boggling blowjob of my life. She was slurping, twisting, pumping my dick with both hands, or sometimes one, or with her tongue, she did so many patters with her tongue that I dont even remember. I probably even passed out for a second. She smacked her tongue with my dick, measured her face against my dick (my dick won), spit so much saliva on it that it fell on my couch. Even gave me a titjob in between which felt just as incredible.

I tried very hard not to cum from just a blowjob but I couldn't control anymore, I told her I was about to cum and she started jacking me off furiously and lowered her face a little. I knew she wanted my cum on her face. And then I let go. The first spurt went past her onto the floor, she was surprised and opened in her mouth to gasp and then the second one went into her eye and she started laughing and thats then the third one went in her mouth.

She quickly closed her mouth and swallowed it and as she swallowed, the rest of the spurts hit her face and then she squeezed out the rest on her hands.

"You've some aim" she said as she started wiping her wiping her face with the tissue I handed her.

She got up and sat next to me on the couch.

"Sorry, I couldnt hold back"

"Clearly." She said pointing to the cum on the floor. "Don't worry hon, we got all night"

As I looked down, I sawe she was still hard as a rock. I leaned towards her and grabbed her dick saying,

"Someone is still hard"

"What are you gonna do about it?" She said looking at me playing with her dick

I turned her around and made her lie down on her back I sat between her legs with ehr dick in my hands.

I looked at her, her tits, and her dick. I was hard in seconds. I started moving my hands and started giving her a hand job.

"I have never given anyone else a handjob"

"Its okay. Take your time. Enjoy it" She said and kept looking at me as I couldnt take my eyes of her dick and her balls.

I started noticing how different her dick was. My dick curved upwards a little, her was curved a little down. I had a mushroom head dick, her dick was almost straight. Her middle part was thicker than the rest, but it was just as beautiful. Her balls were firm but smaller than mine. Mine were heavy and hung a little lower. We both were uncut though.

"I like that you have foreskin" I said, I really did. It looked good on her dick.

"Me too. I liked that you have foreskin too."

Then I quietly jacked her off a while as she put some music on her phone. I started spitting on her dick every now and then. Inching my mouth closer and closer.

After a while I saw her hips moving and I felt my mouth watering. Only so much you can stay near a dick like that and not taste it.

I lowered my tongue, pulled the foreskin back and slowly touched the tip of my tongue to her head, as if dipping a toe in a cold pool before jumping into it. There was a lot of precum already dripping out of her that that was the first thing I tasted.

It was a little sweet and salty. The first taste felt weird but for some reason I wanted to taste more. For some reason I still wanted to feel taste in my entire mouth. So I lowered my tongue even more. I started licking her head. It tasted so good in a few seconds. I couldnt get enough of it.

I was also jacking her off the entire time. The more I licker her head and jacked her off, the more she moaned. Thats when I dared even more. I went lower and took her head inside my mouth, and closed my lips around her head. I did not stop licking her head. But I kept going lower and lower and started taking more and more of her dick inside my mouth.

I dick sprang up when I felt her dick inside my mouth. It filled up my mouth. I couldn't believe I was finally sucking a dick. It felt so good having a dick inside my mouth. Especially a fat dick like hers. Soon enough I had more than 4 inches of her dick inside my mouth while. I started moving my head up and down, while playing with her balls (which had become tight by now) and licking her head every now and then.

Thats when I felt her hadn on my head, pushing ever so slightly. I knew what she wanted. So I went in, opening mouth and filling up the rest of the space left in my throat. I tried to touch my nose to her crotch but I couldnt. She was too thick for me for the first time. I could only take 5 inches in. But that feeling of her dick's head touching the end of my throat made me cum.

This was the first time I had cum hands free. My dick had been resting on her feet and I shot ropes on her leg while I deepthroated her. I could only keep her dick in for a few seconds and I took it out with my saliva coughed back on her dick. I looked at her, she had her eyes closed and she opened it as I looked up to take a breath.

"You're a fucking natural" she said, "you're sucking it really well for the first time"

"I love the feeling of your dick in my mouth" I said licking it from top to bottom and back to top again.

"Yes, I can see that", she said referring to my cum drying on her legs.

"That was hot, that was the first time I've cum hands free" I said licking her balls along with her dick

"I guess tonight is a lot of firsts for you" She said caressing my dick with her feet and moving her hands through my hair.

"Best birthday ever" I said and went down again to deepthroat.

This time she started moving her hips ever so slightly as if she was fucking my throat. I must have lost track of time sucking her dick cause after a while my jaw had started to ache. So i took her dick out of my mouth and started jacking her off.

"Some body is hard again" she said playing with my dick with her legs

I was raging hard. I didn't know sucking dick is gonna make my dick harder than it had ever been.

"I want to try something before I fuck you", I said right next to her dick. And I touched our heads together, mixing our precum and my post cum wetness as well. That made me even more hard. I then played around a little with her and my dick like that for a while (which i recently found out is called frothing), making my head wetter and wetter with her and mine precum.

I couldnt take it anymore. I had to feel her ass. I had never fucking anyones ass before so I assumed its gonna make me cum quick so I got up and got myself an orgasm delay condom for me from my stash along with some lube.

"Wow, you're prepared" she said looking at the lube.

"You never know when you might need it" I said putting on the condom and then as I was about to squeeze some lube on her ass in missionary, she turned around and got on all fours.

That magnificent plump ass was looking directly at me now. My dick moved a little on its own because of the view.

"You read my mind", I said spanking her ass hard a couple times and then squeezing some healthy amount of lube on her ass and asshole.

Thats when I saw the anal plug that was there in her asshole.

"Was this here the whole time?", I said impressed

"You're not the only one who planned to hookup tonight" she said with her head resting of couch arm and looking back at me.

She started giving me directions on what to do. She told me to massage her ass cheeks a little and then slowly insert a finger in the asshole to spread the lube. I followed what she said. I spanked her a few times while doing that. I could the see her ass turning a little red with every slap.

She then told me to increase the number of fingers slowly to three while still applying lube. I did what she asked. What a view it was for me. On top my three fingers coming in and out of her asshole and at the bottom, her hard dick moving around with the motion of my fingers. I immediately grabber her dick from the back adn started milking it. I felt as if I was milking a bull. My dick liked that, it jerked again on its own.

I couldnt take it any more. I pulled out my fingers, got on top of her, put some lube on my dick and then started slowly inserting my dick in.

Since my head was bigger than my shaft, it took a while to put my head in. But thats when I realised asshole and vagina differ in one key aspect - the asshole will willingly suck the head of the dick in cause of the muscles around it. So even if I was going slow, once more than half of my head went in, the rest of it got sucked in immediately and then in that motion, half of my dick went in as well.

That blew my mind, she screamed a little, asked me to give her a minute while I enjoyed the view of being inside someone's asshole for the first time. I loved how the asshole was squeezing hard on my shaft and my head inside. Her insides were tightly wrapped around my dick, inviting me in even more.

After a few seconds, she told me to put the rest in as well. And before her sentence was over, I was all the way in, in one quick motion, which made her scream again. I loved that scream. My dick started twitching inside her ass.

I gave her another few seconds to get adjusted.

"Another thing off my bucket list." I said kneeling down near her neck and biting her back and neck a few times.

"This is new for me too, you're the biggest I've taken" she said turning around and kissing me.

That was my cue to start move. And move i did. It was hard for me to stop after I started. Even I wouldn't have been to stop myself.

I had gone to another plane, I rested both my hand on her waist and put all of my weight on her waist and started fucking her as if I am trying to bury her into that couch. I dont know how long that went on but I finally came to when she buried her nails into my wrist and I felt the pain.

I realised what happened and I took my hands away and got on top of her prone bone style. And then wrapped my arm around her neck as I kept fucking her ass. That when I realised, prone bone is meant for anal. The position perfectly lines up.

"No fucking pussy in this world can compare to you ass", I said as I squeezed her neck further and didnt stop fucking her ass for a second.

She started tapping on my arm when she wanted to breath but I was again too out of it so she in an attempt to breathe desperately, scratched my neck and pushed me away.

My dick flopped out and I sat down on the couch as she coughed and gained her composure. She turen around and looked at me like a feral cat and said,

"You like rough huh, I'll give you rough".

She jumped on me and put my dick in her ass and started grinding hard on my dick. And on every motion her half hard dick and balls flopped around and hit my abs and hers again and again. She took both her hands and squeezed my neck hard and that turned me on even more.

I started spanking her to go harder and harder on my dick. And the harder she went the harder her dick hit my abs. Soon I realised her dick was getting harder because of it and I grabbed it and used it as a joystick to dictate her motion.

Then after a while, as she let my neck go a little after squeezing her nails into it, I picked her up a little and started fucking her from below. Every time pulling out and pushing my entire dick in.

This got her over the edge. Her dick was now so hard that it was barely moving on my thrusts. I knew what was coming. I increased my speed and make the thrusts shorter. She couldnt stop moaning. Her moans were actually being broken by my thrusts, thats how fast I was fucking her. Her eyes closed and rolled back and her mouth stayed open but no voice came out.

I knew it was any moment now, so I kept doing what I was doing. My ass was gonna go into spasm but I told myself this is was the hip-thrusts are for at the gym..

Thats when it hit me, her first big thick spurt of cum tonight, hit me right on the tip of my nose to down to the end of chin. I liked that. The second thick spurt hit me right across my chest. The third and fourth one were also on my chest cause I didn't stop fucking her, and then the fifth, sixth and seventh landed on my abs and the rest trickled down her dick and onto the balls and onto my thighs.

I finally stopped for a minute to let her breath. She opened her eyes and finally saw the mess she made.

"I guess I have a good aim as well" she said reaching for the box of tissues. I stopped her.

She looked at me, and as she looked at me, I took my tongue out and licked the cum that was on my face.

She moaned and said, "let me guess, another thing off the bucket list?" and then started grinding on my again slowly.

"Something like that" then I picked her up and made her lie down on her back on the couch and started fucking missionary while sucking her tits.

"You're an animal" she said as I grabbed dick with one had and used as support while I sat up and started fucking her.

Thats when I realised holding on to dick in this position is a great support for you to go absolutely mad man on someone's ass. I recounted the amount of times I as fucking some girl in this position where a dick would have come in handy.

I started jacking her off as well and soon I lost track of time. I loved the feeling of her cum on my chest and every now then when I felt like I scooped a little cum which was mixing with my sweat and swallowed it. Her cum was sweeter than her precum. I liked that. It was very thick, I liked that too. The thick cum felt nice in my mouth.

And just when I felt I had ran out of cum to keep in my mouth, soon, she shot more. This time I bent it towards her so I could from her body. Her cum almost reached her sweaty tits and then her abs.

I immediately bent down and licked the ones on around her boobs.

At this point my waist had started to give out so I took a break, pulled my dick out, saw the asshole that I spread open, then went to lick the cum off her body and took her dick in my mouth to get her hard again.

"I need more cum" I said sucking her dick

"You're gonna empty my balls at this point" She said moving her waist with my motion

"That the point. I want to see you shooting blanks tonight"

After sucking her cum covered dick for a while, I bent her up so that her dick is pointing straight on her face and her asshole is up facing the ceiling and her knees were right next to her boobs.

Then slowly I put my dick in and moved up and down with my knees.

"Fuck you're gonna break my back tonight birthday boy"

"As I said best birthday every"

I couldn't pick up much speed this way but I could see I hit a certain angle in her ass. I doubled down on that spot - taking my dick out and pushing it back in with force in that particular spot.

"I think-ahhh fuck--you're-fucking shit that feels good- ahh fuck- hitting my- fuck,fuck,fuck-prost-"

And that was it. With that she shot her third load of the night right on all around her face and the rest dribbled on to her boobs.

I took her ass down, held it in mid air and started fucking her while some cum was still dribbling out, and because of the thrusts it started going around, some came on me some on my couch, some maybe on the floor, I dont know.

At this point, all I could see was her almost hard cock and her tits were juggling with every thrust. I couldnt take my eyes of them. That was too much for me. I took all the energy that was left and put it in my waist and started fucking her like jackhammer.

Suddenly I thought I broke something inside and I was about to stop when her eyes started to roll back and I knew she was about to orgasm and I was close too. So I kept going.

I had started seeing stars when I saw some cum dribble out and fly around again and it hit me in the neck and with one big deep thrust I shot my biggest load yet of the night into the condom in her ass but kept fucking to squeeze every drop out and collapse on her when done.

After catching my breath on top of her, I got up and sat on the corner of the sofa and looked at her. And together we both realised the same thing - she reached around and felt her ass and saw my cum dripping out, and I looked down.

Thats when I realised that sound of breaking something was the condom. My dick twitched again.

"Holy fuck you broke through the condom"

I smiled and said, "Another thing off the bucket list".

She smiled and lied down.

We both caught out breath for a while. Then we ordered some food, ate it naked. And then went right back to fucking.

We only actually fucked one more time that night cause she said her ass was already sore from the first round. But we blew each other off, jacked each other off, 69-ed each other, and did all we could do all night and tired each other out by 5am and went to sleep - passed out actually.

We fucked that entire weekend. And it hasnt stopped yet. We liked each other too much to stop seeing (and fucking) each other.

So I guess this isn't the story about a hookup but my first dating experience with a trans woman. Hope you enjoyed. Let me know if you'd like to read more.