My First Trans Experience - WOW!

Sitting alone and feeling bored in my hotel room, my mind began to wander. I was visiting Vancouver for a work conference and began feeling horny. I had visited massage parlours before on work trips and found them to be very hit or miss. This time I was feeling like trying something different...

Recently I had seen some ads for trans escorts and was blown away by how hot some of them looked. Wanting to do some further investigation, I watched some transgender porn videos online. I found the Asian trans women to be especially hot. There were some videos of guys who traveled to Thailand and filmed themselves with Thai ladyboys. Initially, I resisted a little when I saw a guy giving head to a ladyboy... but the bulge in my pants told me that I didn't have as much a problem as I thought I did! I started jerking off to a bunch of trans porn and, over time, I couldn't get the idea out of my head. I wanted to know what it was like.

I was in town on business and I had my evenings off. This particular Sunday night I was feeling pretty adventerous and started looking up ads for escorts.... transgender escorts to be exact. I was so nervous. What if this was a mistake? What if she doesn't turn me on? I don't want to be rude but I'm not going to hook up with someone that I'm not attracted to. What if I find myself with a cock in my face and I'm just not into it? Well, once and for all, I was going to find out. I had recently turned 40 and thought I was due for a little excitement in my life. I went to a good local site for escorts and started browsing. A small handful were super attractive and had me very very curious.

After about 90 minutes of browsing and then trying to find online reviews, I finally decided on a beautiful Asian girl named Ginny. Her profile pics were both classy and stunning. You could tell that they were professionally done and looked amazing. I can't say I love it when any escort is spread eagle and exposing all the goods on their profile pics. Nice to leave a little to the imagination. Ginny had some photos of herself dressed in a tennis outfit. That's what did it for me. I had to get a look at this girl up close. As much as she looked beautiful in the photos, I still had no idea what to expect. I was dying to try this but still so nervous. I couldn't get the profile pics out of my mind. Long sexy legs, perky tits, beautiful eyes that were staring straight into the camera and saying "are you man enough to be with me?" Combine all of that with the sexy tennis skirt... I just couldn't get her off my mind. I had to see what she was hiding under that skirt!

I decided to text Ginny and see what happens. Much to my delight, she responded within a couple of minutes and was very communicative and easy going. This put me at ease so I decided it was time to pull the proverbial trigger and go for it! She had an appointment available as someone had just cancelled. My lucky day as she sees only 1 or 2 people each day and she would have been unavailable had someone not just cancelled.

She told me to come by at 9pm. The countdown was on! I had to prepare! I jumped in the shower and made sure I was nice and clean in all the right areas. I shaved, moisturized, brushed teeth, etc etc. Needless to say, I was rearing to go and pacing my hotel room in a semi-tumescent state for half an hour until it was time to go. She lived pretty close by in a super nice downtown highrise. This was a good sign that I may have a positive experience. She said she worked by herself so I didn't need to worry about some handler or mamasan answering the door and demanding money as soon as I walked in the door.

At 9pm, I buzzed upstairs and nervously rode the elevator up to the 25th floor. I very timidly knocked on the door and waited with bated breath. After a few moments, the door slowly opened and I was stunned by what I saw!! An absolute stunner stood before me in the super sexy tennis outfit from the photos (I mentioned how much I loved the outfit so this was a great surprise). She stood about 5'10" with the body and stature of a model. My mind was racing "Holy shit! She's hot! I'm so fucking horny right now!!" I was terrified that the photos may not match and some guy in a dress might answer the door. Boy was I wrong! I'm 6'3" so I wasn't intimidated by her height. On the contrary, it was sexy as hell.

Ginny greeted me with a lovely peck on the cheek and nice hug. She smelled amazing. I felt like my knees might buckle as she was giving me the hug. I think it was a combination of nervous excitement mixed with relief over the fact that she was smokin' hot and seemed super sweet and friendly right out of the gate.

Ginny took my hand to lead me to the couch and noticed that my hand was shaking. "Are you ok?" she asked. "I'm ok. I've been to massage parlours before but this is my first time with an escort and I'm just a bit nervous." She went to the kitchen and brought back two glasses of wine. "This should help" she said with a grin. I had to catch myself a few times because I was staring at her and completely lost in my own thoughts. "damn that's a hot skirt... I wonder what's under there?"... "she must think I'm a mess... drink the wine, relax, and make some conversation before this evening starts going downhill!" Thoughts were racing through my head but the wine quickly went to my head and I found myself starting to relax.

I was starting to chill out and make normal conversation. But I couldn't help but stare at her chest whenever she looked out at the beautiful view from her condo window. "So did you grow up in Vancouver? (I want those tits in my face!) So what do you like to do in your downtime? (I really want to suck on those perky C cups... I can see the outline of your areola through your tennis shirt) Oh, you play video games? (fuck, I'm getting hard... is that a good thing or a bad thing... well, she's an escort so probably a good thing!) What games do you play? (oh man, I would give anything to slide that skirt up and see what's happening down there)."

I was managing to keep the conversation going but was so relieved when she leaned toward me with a look in her eyes that said kiss me (oh shit, is that allowed?! I think she wants to kiss but I don't want to piss her off if I'm wrong - I've seen Pretty Woman!) I decided to ask if I could kiss her and to my delight, she said "yes, please." We locked in a passionate embrace and our lips came together as fireworks went off in my head.

Whatever concerns I had about being with a trans woman flew out the highrise window and I pulled her in even closer as our tongues gently touched and moved around playfully. By now, I was rock hard and didn't care if she could see the bulge in my pants. It was literally pulsating in my pants with a longing for this girl that I hadn't felt in a long time.

I discovered a little later that my underwear was a mess. I was leaking precum! I hadn't done that since I was 18 and only when I was super turned on. I'm 40 years old! What's happening to me?! I need her to touch me... touch my body... touch my nipples... touch my cock. I'm drunk with excitement and a yearning that I didn't know was possible. Why had I never done this before? We continued to kiss passionately and our hands explored each other's bodies.

Her tits were amazing. So perky and full. Nipples hard and protruding through her white cotton tennis shirt. She had a pleated teal tennis skirt on and I was sure I had seen some movement down there. I slowly slid my hand up her inner thigh until I reached her silky soft panties and that's when I felt it... my heart skipped a beat... I was making out with a beautiful woman and I just laid my hands on a rock solid cock that sent shivers down my spine. I needed to see this immediately. I couldn't wait any longer. I dropped to my knees in front of her and raised up her skirt. Her smell was intoxicating. I couldn't believe what I was looking at and also couldn't believe my reaction to it. I had never wanted something so badly."I need to get this in my mouth or I'm going to burst with excitement."

I started kissing her inner thighs and just breathing in her musk. I was worried I might cum in my pants I was so excited. I kissed the bulge from the outside and as I was doing so, I noticed that the tip was peaking out over the top of her sexy panties. This was it. At this point, I can't believe I even considered the idea that I might not be into this. I don't know if anything has felt this right. I flicked out my tongue and softly licked the tip of her cock. Lightning bolts shot throughout my body. I need this in my mouth. I want her to fuck my face. I want her to cover me in sticky hot cum. Please. Please. Fuck my face. I proceeded to pull down her panties and took as much as I could in my mouth. I loved it. I could taste a little drop of precum at the tip of her cock. This is amazing. I slid up and down on her cock with my lips and trying my very best not to let my teeth get in the way. This was my first time doing this and I wanted to do it right. She had a beautiful cock. A good six inches and wanted every last bit inside of me. As I worshipped her cock with my mouth, I reached up and started rubbing her hard nipples with my hands. At this, I heard some soft moans escaping from Ginny. She seemed to be enjoying the events and I was in heaven.

Next, I pulled down her panties and took a break from the cock to explore some other areas. As I continued to pump her shaft with hand, I slowly lowered my head and started to softly caress her smooth balls with my tongue. I swear I was drunk from the smell of her... I love the smell of girly body lotions, perfumes, etc. This mixed with the site of a few beads of sweat dripping down her inner thigh had my heart pounding.

The next part just happened out of the blue. If you had asked me earlier, I would have sworn that this would never happen. As I was flicking my tongue around her balls and inner thigh while continuing to pump her hard cock, I pulled her forward to the edge of the couch. I grabbed a leg, pushed it back and started vigorously tonguing her flawless ass. This is not something I normally do with anyone but I just couldn't get enough of her and I couldn't help myself. After a minute or two, I just couldn't wait to get her cock back in my mouth. All I could think about was having her explode in my mouth, cum dripping down my chin, as I sloppily drink it all up. I don't think Ginny was expecting this. The mild mannered, shaking guy from 10 minutes ago is now between her legs, and licking and sucking her cock like his life depended on it.

I begged her to cum on me, cum in my mouth, cum on my face... make me yours... I want to drink you. Please baby... I need this. I need you. I want you inside of me but at this point I'm too worked up and my mind isn't considering what might happen next. I continued to suck her cock with all of my pent up excitement about this moment. I hadn't known if it would ever happen and boy was I happy that it was.

At this point she stood up and leaned over me as I leaned back against the couch. She proceeded to fuck my face like I had begged for moments ago. "You like that? You like having a hot slut fuck your face?" I just smiled and groaned as my mouth was full of cock and I was in ecstasy. She started to get into a rhythm and pick up the pace a bit. Her balls were softly slapping on my chin and I was excitedly getting ready for the climax. A few moments later, I felt her tighten up and moan as she shot the initial spurt down the back of my throat and then proceeded to pull back and cover my lips and chin with her hot cum. I was drunk with excitement... this is amazing!! I licked up every last drop and softly licked her now softening cock.

"Wow, I didn't see that happening when you first walked through the door" she said with a relaxed look on her face. "Yeah, I guess I got a little carried away there. I couldn't help myself. You are sexy as hell and I just want you so badly." She then asked if I wanted to take a break or continue on in the bedroom. "What do you think... my balls are throbbing in pain at this point." I literally felt like I did as an 18 year old when I would go on a date and basically have a hard on for 90% of the date... the blue balls in those days were epic. At least I knew a release was coming soon!

Ginny took me by the hand and led me into her very girly bedroom. It was super clean and smelled wonderful. As if it was even possible, I think I was getting hornier looking around her bedroom at her sexy outfits and some lingerie that happened to be visible in her closet. I know I had some reservations earlier on about seeing a trans escort. I can honestly say that those thoughts were long gone at this point. I was so fucking turned on at this point and all I could think about were the ways that this girl could make me her sex slave. At 7pm I had told myself that I would draw the line at oral. It was my first time doing this and I should probably take things slowly. Cut to 9:30pm and I'm daydreaming about Ginny pounding my virgin ass in every position possible! Just because I was warming to the idea didn't mean I was going to instigate things. I was still pretty shy about things and while I assume that my donation probably covered full service, I wasn't totally sure.

After bringing us two more glasses of wine, Ginny climbed onto the bed next to me and got cuddly. We chatted for a few minutes while we drank our wine but it wasn't long before we had our tongues down each others throats, hands exploring each other's bodies. I was in heaven. I hadn't had a passionate makeout session like this in years. My cock continued to throb and leak precum. I was terrified that I would explode as soon as she touched it. I had never had issues with being premature... but I also don't know the last time I was so turned on.

Ginny had slipped into a little silk robe and silk panties while I was lounging in just my boxer briefs. I made no effort to hide my massive erection. As we were kissing, Ginny mounted me and was grinding my lap as we kissed. I couldn't handle much more. I slid my boxers off and begged her to touch it. She slid her panties down and grabbed her stiff cock. She proceeded to grab mine as well and jerk our two cocks at the same time. Ginny commented about my size as my cock was bigger than hers but not by much. I have a solid 7 inches with decent girth. Ginny was at least 6 inches and not as thick but well proportioned and beautiful. I was dying to get it in my mouth again.

As she pulled back her foreskin, I could see the head glistening in the candlelight. I loved seeing her stroke both of our cocks. I loved watching scenes online of a man and a ladyboy rubbing their cocks together and jerking them off with one hand. I couldn't take it anymore. I slid down while also wrapping my arms around her thighs to prop her up and get that beautiful cock in my mouth again. She pumped in and out of my mouth for a minute while reaching down and gently stroking me at the same time. I was in ecstasy.

"Lie face down on the bed" she said as she hopped off me and proceeded to grab a pillow and put it under me. Ginny left the room for a few minutes and a little bit of anxiety started kicking in when I started to think about being face down, butt in the air in a random downtown condo. Luckily, anxiety turned to a chuckle when I thought about how I must look right now. As Ginny walked back into the room with a little box in hand, I went back to being excited and curious about what she had planned. I had told Ginny that I wasn't planning to involve my previously unexplored hindquarters... but as she strolled back in, looking sexy as fuck in her silky lingerie, I quickly came to the realization that I would do whatever this beautiful woman wanted to do. I was putty in her hands and she knew it. She looked me in the eye and said with a confident (but somehow non-threatening) tone: "I'm going to take that virgin ass."In less than an hour, I went from "maybe oral" to "take all of me. I'm yours. I'll do whatever you want."

Ginny climbed onto the end of the bed. She grabbed my hips and adjusted me a little. My head was in pillows and stuffed animals so I couldn't really see what was happening. I was buzzing with anticipation. As I was daydreaming about what she may be planning, she spread my ass cheeks and I felt something wet tickling my... backdoor. It felt amazing. I assumed it must be a lubed up toy of some sort from her little box of goodies. Why had I been nervous? This feels fantastic!! After a minute or two of this awesome feeling, I had to turn my head around to see what kind of toy she was using. I turned my head to the other side where I was able to catch our reflection in the sliding mirrored door. I was in shock. This sexy Asian woman had her face buried in my ass!! It's no wonder it felt so damn good. There's a first time for everything, I guess!!

Now this is what I call full service!! Extreme GFE! Although I wasn't necessarily expecting to involve that area, I was very happy that I had decided to give the area a thorough cleaning just in case!

Dirtier and dirtier thoughts were entering my mind as I blissfully enjoyed her rimming my ass. Is she going to stick something in there? A pinky? A toy? Her cock? All I could think about at this point was her pounding my ass with that gorgeous cock of hers. Take all of me. Make me yours. I felt myself gently wiggling and repositioning so I could present myself to her and make it easier to penetrate me with whatever she wanted. After a few minutes of tickly ecstasy, I felt something pressing on my back door. "Relax sweetie... just take a deep breath and let it in... I promise you won't regret it." I tried to think relaxing thoughts and did my best not to squeeze tight (as was my initial instinct).

Ginny slowly and gently slid a finger in and out of my tight ass while I moaned with pleasure. She was about to switch to a toy that was slightly larger than her finger but I couldn't take it anymore. "Please fuck me, baby... please... I need to feel you inside of me. I need to know what this feels like. Take me." She just gave me a sexy smile while she stood up and took out a condom and a bottle of lube. I was looking over my shoulder at her and getting so aroused. At that moment, she grabbed me by the back of my head and shoved my head back down into the pillows. I could feel a cool squirt of lube land on my ass and a moment later, I felt the head of her rock hard cock pressing against my tight ass. "Hey! Whoa! Maybe you should slow down a bit. That kinda hurts a bit." Then, all at once, I relaxed my sphincter and BAM - her cock slid right in and I felt her balls softly slap against me. "Oh my god, oh my god, this feels amazing. Don't stop. Don't stop." I was in heaven. Her 6 inch cock was just the right fit and it was hitting my prostate every time she thrust herself deep inside of me. I had never felt this before. "How have I never done this before?!?! It feels so good. Please keep fucking me, baby."

I have no idea how long we stayed in this position but after a period of time, she instructed me to roll over. She propped a few pillows under me and without hesitation, she grabbed my legs and pulled me toward her throbbing cock. My willing ass took all of her with very little pushback. I had gotten the hang of this and I wanted more. I had enjoyed getting fucked from behind like that (especially when I looked over in the mirror and caught a glimpse of the scene that was going on!). This time was even better though. I looked up and took in the beautiful site before me. A super fucking hot Asian chick was pounding my ass! I couldn't believe it.

My cock was dripping precum from all of the insane excitement and the prostate play was adding to it. She reached down and wiped the tip of my cock and rubbed it along her bottom lip as she licked it a moment later. Damn she's hot. She then leaned forward and kissed me passionately while continuing to thrust in and out of my tight ass. After a few minutes like this, Ginny leaned back and picked up my legs and put them over her shoulders. She pushed my legs together and leaned over me while pushing my legs toward my head. This allowed her the deepest penetration. It hurt a bit in this position but I honestly didn't care. Her stiff cock was hitting my prostate with every thrust and I loved it.

I moaned with pleasure after each thrust. She then put my legs down and started to play with my nipples. I hadn't told her this but my nipples are my number 1 erogenous zone. I didn't need to tell her. She could see the look on my face as she gently played with my nipples while slowy pumping in and out. I felt like I was about to cum just from the penetration paired with nipple play. I asked her to go easy on the nipples because I wasn't ready to cum yet. I literally felt like I was in heaven. The site of this beautiful girl having her way with me was too much to handle. She appeared to be ready to cum because she started picking up speed in a rhythmic fashion. After a couple of minutes she was pounding my ass pretty hard. "I know I'm going to feel this later but right now I don't give a damn. It feels too good... I don't want you to stop. Fuck me, baby. Fuck me, baby. I want you to come again..." I made eye contact with her and we locked eyes "I'm all yours... do whatever you need to do to make yourself cum again. I want that hot load all over me."

"Where do you want it, sweetie?" I didn't need to think about it, I quickly spat out "please cum all over my cock and balls... I want to feel your hot load all over my hard cock... I want to stroke my cock with your cum!" I think Ginny liked the sound of this because she started pounding which got me moaning plus she had a look on her face that told me she was close. I purposely left my cock alone because I knew I was too fucking horny and there was no way I would last more than a couple of strokes. I needed to feel her cum on me before I wanted to make that happen. She bit her bottom lip as her balls rhythmically slapped my ass on each stroke. I was wimpering with pleasure (and a little bit of pain) and I knew she was close so I started begging her to cum on me. "Please baby, let me feel your hot, sticky load all over me." At this point she quickly pulled her sexy cock out of my gaping ass and ripped the condom off. With one or two quick strokes of her cock she began giving me my wish. She shot at least 3 or 4 nice sized ropes all over my cock and I was immediately sent to another level of pleasure that I didn't know I could reach. The site of this gorgeous girl with perfect tits stroking her cock and covering me with her seed was blowing my mind. The feeling of hot cum (that wasn't my own) dripping down my throbbing cock onto my balls was a level of pleasure that I could no longer bear. I grabbed my cock as tight as I could and used her cum to pump my cock furiously for all of 3 seconds before I started spurting out shot after shot of pure ecstasy all over my stomach and chest.

What the fuck just happened!?! I lay there with cum all over me and the bed sheets. A goofy smile plastered on my face. "Ginny... words can't describe how amazing this was... you will dominate my dreams until I can see you again. I am so thankful for the amazing time you showed me!!" She leaned down and kissed me passionately while our bodies came together and now we were both covered in sticky white substance. After a minute or two of hot kissing, she popped up with a smile and said "come on, let's get cleaned up!" She grabbed my hand and pulled me into a lovely steam shower.

We took turns rubbing the other one down with body wash while playfully kissing and teasing each other some more. Surprisingly, I was already back to a semi-tumescent state. It was the site of that stunning body, our two cocks gently rubbing against each other, warm soapy water... I started to stroke both of us gently... whoa, whoa, whoa, stop the clock! Chill out! Ginny was amazing and I didn't see her look at the clock once but I didn't want to overstay my welcome. I was spent but this was still really nice. I knew our time was up so I just enjoyed these few moments before she stopped the water and began to pat me down with a giant fluffy white towel that smelled amazing (like her).

Ginny invited me to sit down in her living room and have a glass of water. I happily obliged. A few more minutes with this beautiful person sounded great to me. She was just so chill. I was in awe... Hot af, plays video games, has the sweetest smile and is just overall wonderful.

After a few minutes of friendly chatting we said our goodbyes. She gave me a great hug with a kiss on the lips and right there I knew I would never be the same again. Ginny awakened something in me that would be very hard to ignore. If I'm being honest with myself, I don't want to ignore it. I don't what this means for my sexuality but I could give a fuck, I need to feel that kind of pleasure again in the very near future!! I hurried back to the hotel to get working on plans to come to Vancouver again as soon as possible.

At this point, I still haven't made it back to Vancouver to see Ginny again but I remember this night like it was yesterday. She lives in my head rent free. Any time I find my mind wandering into dirty thoughts, it's her that I see. Any time I'm struggling to finish, all I have to do is think about that night. I imagine the site of her leaning over me...

Until we meet again...