What an Amazing Life - My TS Lover

Thanks for clicking on this story.

I have been trolling around Literotica for a couple years now, mostly downloading stories to the hard disk of my notebook, to fuel my masturbatory fantasies while I am on the road.

Probably like most of you, I am someone that people of the opposite sex never seem to pay attention to when passing on the street. Family genes (Dad's?) left me with a bald spot larger than the "hairy part" on top of my head. Similarly, family genes (Mom's?) left me with a cock the size of which would certainly preclude my starring in the kind of movies I prefer watching. Who would pay money to watch me perform with the 6 inch, not particularly thick, cut cock I inherited? So smart of my folks to have an inch or two cut off before knowing how big it would eventually be!

To finish with the self-deprecation, too many years of "the good life" have left me with a more ample "middle" than I would prefer to carry around.

Get the picture? I am nothing special, at least to look at!

Recently, among the dozens of stories I downloaded from Literotica for later pleasure, I found one from a woman about one of my favorite topics, Transsexuals. Reading it a couple days later, I splashed an extraordinarily great amount of warm juice, placing myself in the middle of the writer's action.

I was so taken by the story and subject matter that I decided to contact her and send my gushing compliments (well, at least in words) for her work. From that message, we have become great friends, sharing lots of thoughts, fantasies, experiences and feelings. It is from having the lovely opportunity to know her that the inspiration for this story comes. If it turns out ok, it is thanks to her editing. If it is awful, it surely results from the writer's limitations.

I am writing this story in little parts and sending it to my sweet friend for her comments and suggestions. If the two of us get this done quickly, this will be the story of a 52-year-old American guy. If it takes too long, he will be 53 (any day now).

Ok, so now I guess you understand that I am probably a lot like you. Hopefully like you, I have been fortunate enough to enjoy some wonderful erotic experiences. Today I will share the first of those with you.

I have realized that the true stories here excite me the most. There is absolutely nothing wrong with reading somebody's fantasy...but...reading about something that I would love to try and knowing that the author has "been there, done that" gets my cock hard and leaking faster than anything else. Therefore, with this in mind, here comes the first of my 100% guaranteed true stories. Everything here actually happened, just this way.

I guess like most young guys (at least those honest enough to admit it), my first sexual experience happened with a neighbor boy. In our early teens, we were so horny and eager to experience all that life could offer, my buddy and I began giving each other massages. What began as a simple rubdown eventually became kissing, nipple licking, stroking of each other's cock and finally honest to goodness cock sucking. My friend mentioned several times how much liquid leaked from my cock when he sucked me. Neither of us knew then what cumming was all about...this was just my pre-cum. He, on the other hand, didn't leak at all but I still remember so fondly, how enormous his cock seemed in my mouth and hands. Honestly, I often wish I could have another chance with it (him).

I never considered myself gay or bisexual. When I finally got a chance to experience pussy (I was 15 and she was in college), I was hooked. From that first day, I went on to enjoy the bodies of many women of all sizes, shapes, ages and ethnicities. I have been fortunate enough to have sex with a delightful Chinese virgin (a colleague at the time) less than half my age (and she wanted very much to have me be her first). I have had two women at once (once in Thailand and again last month in Argentina).

I have met and had great sex with quite a number of wonderful women I met through chatting. I chatted with a travel agent in Toronto and asked her to recommend a good hotel for an upcoming business trip. When I checked in, the front desk guy said there was a woman waiting for me in the bar, something totally unexpected. We had never discussed meeting. After sharing a glass of great wine, she accompanied me to my room and let me thoroughly enjoy my first shaved pussy.

Unlike many, I have never been disappointed with meeting someone from the net. I have had sex with Caucasians, Blacks, Latinas, Asians (oh, how I love them) and one redhead, something I want so much again.

I travel constantly and have enjoyed lovely women in the US, Canada, Mexico, Brazil (yes, it is true what they say), Argentina, China, Vietnam, Philippines, Thailand, Hong Kong, Singapore, Malaysia, Italy, Germany, Romania, and the UK. I guess I can be charming when in the company of a lovely and desirable woman.

I have sucked more than my share of sweet pussy, have cum in more cunts than I can count, have had women beg to swallow my warm cum and have had plenty of anal sex (the first time honestly was an accident but once we both felt my cock in her tight asshole, we wanted it again and again). I have gone through enough rubber in my life to keep Michael Schumacher in tires for an entire season.

What I am saying here is that I thought I had experienced most of what "straight sex" has to offer. If it can happen to me, surely it is happening or can happen to you too. I insist to you that I am nothing "special" at all!

Thanks to the internet, I have had the freedom to explore much more of my sexuality. I don't know if I have the courage to lurk around the "unusual" corners of an adult bookstore but with the internet, I can cruise wherever my fantasies take me. This got me interested in she males.

I guess it was the lovely recollection of sucking my young buddy's cock, of trying unsuccessfully to fuck him (and him me) as well as my love for women that made me interested in ladies who have the best of both worlds.

Cruising the Trans sites, reading erotica on the topic, I found my frequent masturbation sessions more satisfying than ever before. The more I read, the more I wanted to know.

Eventually, I found myself logging onto Gay.com and lurking around the transsexual (m to f) room. After chatting with so many folks there, one day I met Patricia. How that would change my life!

Of course, one of the limitations of the net is that one never knows who the other person really is. Although I am unable to understand why, I guess many people present themselves not completely honestly. This is a chance we always take.

Patricia and I began chatting openly in the room and eventually privately on Yahoo messenger. According to her photos, she was an absolutely striking woman, living in the Philippines. She appeared to be about 5' 7" and maybe 125 pounds. I guess that she was about 25 at the time of those photos. They showed straight black hair to the middle of her back, a model's hourglass figure with proud firm breasts, and a smiling face that could have melted the heart of the hardest man (and likely, women). In all, Pat was surely too good to be true. Pat was probably a guy even older and fatter than I, living in Kansas City and out to get his kicks by leading me on with a model's photo downloaded from somewhere.

Over time, Pat and I shared many of our secrets. Although she would never send me a photo more revealing than her on the beach in her string bikini (what a sight), she told me she had a very functioning cock hiding in that thong bottom. Eventually our chats became cyber-sex and the time we masturbated together on webcam, I was completely hooked by this amazing woman with the very hard and VERY functioning cock. Watching her shoot for me was almost more than my heart could stand.

At that point in my life, I was spending a lot of time in Asian on business. I was visiting China, Hong Kong and Singapore mostly. On those trips, I was lucky enough to meet quite a number of lovely and very sexual ladies (including that wonderful Chinese virgin I mentioned before) but Pat always stuck in my mind. I had to meet her; I had to find out what Trans sex was really about. So, I finally made plans to visit the Philippines as part of one of my upcoming business swings.

Pat and I agreed to the date of my visit and I booked a suite in a prestigious hotel in the center of Manila. I arrived and checked in, finding the room large, comfortable and more than satisfactory. If "this" was really going to happen, I wanted to impress Pat by treating her like the lady her photos made me believe she was.

I unpacked and carefully organized all my clothes, something I rarely bothered with moving constantly from hotel to hotel, country to country. Everything had to be just perfect. Finally, I took a long shower in the huge stall (would Pat eventually want to join me there?). I paid careful attention to cleaning my asshole (was that because it felt good or...?) With difficulty I resisted the strong temptation to get myself off...would Pat want and appreciate what I was keeping stored up in my balls?

I carefully shaved, brushed my teeth as if I were trying to remove the enamel, sprayed myself with much too much A-Men, and then tried on every single piece of clothing I had brought. How silly is an overweight guy trying on pair after pair of briefs?

We had made a date to meet at a Starbuck's directly across the street from the hotel. If you have spent time in Manila, you'll know the place, and therefore the hotel.

I was so nervous and anxious, knowing my ultimate fantasy was either going to come true in the next hours or that my trip to Philippines had been a complete waste of time and money. Of course, I got to Starbuck's about 15 minutes early and started out with a large coffee. I sat on a stool in the window slowly pulling on my coffee, watching the people come and go and those passing in front of the store. The longer I waited, the more coffee I drank, the more nervous I became...eventually, I had been there about 45 minutes (meaning she was 30 minutes late) and decided I had been a fool for thinking Pat was real, for getting my hopes up, for spending so much time and money coming here.

I finished my coffee, got up to leave and then decided (since I had absolutely nothing better to do) to order one more. I stood in line, swiveling my head between the people in front of me and the door, wishing/hoping that my Pat would enter and fulfill my fantasy.

As I got to the head of the line and started to order, I felt a hand on my shoulder and a soft but husky voice whispered in my ear, "Roger?". In front of the young Starbuck's kids, I jerked my head around and was looking directly in Pat's eyes. To this day, I still remember the emotion. She introduced me to her friend (a guy that she wisely asked to escort her to her first meeting with a new cyber-friend) and then took over when she realized my voice had failed me, ordering us three coffees.

They made small talk (I had seemingly lost my ability to speak) while waiting for our coffee. When it came, we found a table upstairs and sat down to get to know one another. Although she properly introduced us, I still have absolutely no idea her friend's name and if I passed him on the street today, I would never know it...it was as if he weren't even there. He did seem gay (that brilliant judgment coming from a guy who lusted after Pat's cock...was he her lover?) All that mattered was that I was finally sitting across from the goddess I had worshipped from our first meeting on Gay chat.

While we chatted and drank our coffee, I suppose I gave Pat and her friend the impression that I wasn't a serial killer or too much of a threat to Pat because eventually he gave her a little peck on the cheek, a huge smile to me and hit the road. Finally, Pat and I were alone together (in a jammed and noisy Starbuck's).

I noticed Pat had a small gym bag with her. Did that mean she was really coming to stay at my hotel? I couldn't concentrate on what she was saying, wondering where this would lead, whether it was a bag full of her used gym outfit, returning from a workout.

During our coffee break, I alternated between being hard as a rock and so confused and nervous (remember, two Starbuck's Grande's by this time) that even Ginger Lynn couldn't have gotten me up...I was a real mess!

Eventually, I asked Pat if she would like to come across the street and have a cocktail in my room...I held my breath until she smiled and answered, "of course, that's why I am here". With that, I finally exhaled, threw out the empty cups, took her hand and escorted my dream cum true down the stairs, out of the coffee shop and across the street.

We entered the hotel and for the first time, I wondered what people would think. Would the bellhops and front desk people "know"? Would they think this Westerner had just picked up a Philippine hooker? Worse yet, could they guess what this magnificent lady had hiding in her jeans? Would they imagine this American "businessman" was taking "her" up to his suite in their five-star hotel to have her fuck his cherry asshole? Would Roger be labeled a fag (and maybe a particularly kinky one) for the rest of his stay in their establishment? The trip across the large lobby to the elevator bank seemed to take hours. I felt I was walking through waist-deep Jell-O.

Finally, we go to my room and she looked around, seemingly impressed with the luxury and furnishings. I was still so nervous and I think she recognized this. She put her arms around me and gave me a very sweet, light kiss on the lips...then asking me if she could take a shower.

I paced around the room for I don't know how long, while listening to the water running. A million thoughts and doubts ran through my mind...

What the fuck am I doing here? I should take off (yeah, dumb-fuck, this is your room and your unpacked suitcases).

What if somehow she is not the "girl" I had seen on the internet?

What if I can't get it up (not much chance of that I realized),

What if she isn't in the mood?

What if and what if and more what if's!

Pat finally came out of the shower, wrapped in a big towel that showed the tops of those proud breasts and tons of leg...I almost lost it right there. Was this real? Was she real? Was IT really going to happen? WHAT was going to happen?

She came to me and gave me another of those soft heavenly kisses, I was so hooked! Slowly, her tongue found its way to my mouth and I reached around her to squeeze her tightly against me...I could feel her warmth and the dampness of the towel through my clothes.

I dragged her over to the bed and gently pressed her down. She reached up, helped me pull my t-shirt over my head, and then pulled my zipper down, all the while boring her eyes into mine. Pat pulled my pants down and then kissed the tip of my already terribly wet cock through my briefs...I still cannot believe this really happened to me, she is real! Boy am I glad I paid so much attention to the choice of shorts!

Still smiling at me, she pulled my briefs down and licked up the drops of pre-cum leaking copiously from my now very hard cock. She wrapped her delicate hand around my cock, looked up at me, and said words I will never forget as long as I live, "Roger, fuck my mouth".

I went crazy, holding the back of her head, feeling her long sexy hair on my thighs and balls as I fed my cock into her tight mouth. Looking down, the sight of this sexy woman still wearing just a towel, seeing her swallowing my dripping cock was more than I could handle. After a few minutes, and fighting to resist filling her mouth with the load I had been saving for days, I pushed her off me and back onto the bed.

I pulled the towel off her and finally saw "IT"; she was cut and very hard. My dream and most wonderful fantasy was really coming true, I was in bed with the most beautiful woman I had ever seen and she had a cock at least as long as mine and was hard from wanting me!

At that point, a million things went through my mind. In my mind, I saw a menu of all the things I had wanted to have happen, if this dream ever came to life. Should I let her suck me off? Should I suck her off? Should we 69? Should we break out the rubbers and lube and argue about who fucks whom?

All I could do was stare at this vision of loveliness, this angel brought to me thanks to the internet. I propped a pillow behind my head and began stroking my cock. Watching me, she smiled and began doing the same. God, here I was masturbating together with my dream she male. We got more and more into it. Watching how hard she was, she watching the pre-cum flow from my cock, we began pounding faster and faster. I could hear her breathing becoming huskier and I knew that together we were reaching the pinnacle. I moved over her and began stroking my cock against hers, the sensations of our cocks touching was electric. Here was the woman of my dreams, an absolute 10 beating off for me. My eyes flew between her angelic face, here long and terribly sexy hair, those tight tits with nipples that made me dizzy and a rock hard and dripping dick.

Finally, I could take no more of this and I began shooting all over her hand, her cock and her balls. When I began, she lost it too and shot so strongly that her warm juice flew up and began covering my hand, my own cock and balls too...it was more than I could have ever imagined. I had never seen another cock shoot before. Had never felt another's warm cream on my skin.

Pat stayed with me for several days. We did what men and women do when they enjoy each other's company. We went shopping together (I was sure the two sexy, young giggling girls in the clothing store "knew". They were very friendly and helpful but I imagined them so curious about who was the "top").

We walked hand-in-hand, window shopping in the big center across from the hotel. We enjoyed a sushi dinner (my idea) and another evening; she introduced me to the local cuisine. I bought Pat two prestigious Italian handbags. I wanted her to have something to forever remind her of me. I knew I would never forget one second of my time with her.

During those brief days, we shared some amazing sex. Even if I had focused so much, for so long on this fantasy, it was better than I could have possibly hoped (how often does that happen?)

Alone in our suite, she repeatedly asked me to fuck her mouth. Often she would sit back on the loveseat and let me stand on the seat cushions, holding the back of her head while pushing my hard dripping cock into her pretty mouth. I remember looking out the window, wanting the whole world to see me.

I also sucked my first cock to completion and enjoyed some wonderful fucking. If you're interested in who fucked whom or any of the other details of our time together, vote and perhaps I'll be motivated to write the second part of my experience with Pat, the most wonderful woman on the planet. I will tell you that those days led me to three of the greatest regrets of my life...years later; I long every single day to set them right and still hope for the chance to.

Thanks for reading my work and thanks again to my lovely new friend for her editing advice and support. I've fiddle-farted around with the idea of writing a story forever, you made it happen!