Several months ago, I met a girl online through one of those paid web-cam site, and she was more than just a girl. She went by the name of Nicole and I knew she was a transsexual, because at the time I was very curious about being with one. She was a very attractive, and passable girl with a great body.
Nicole was about 5'6”, weighed about 120 pounds, had dark hair, dark eyes, nice little perky tits with hard little nipples, great legs, a great, and a pretty face, especially when she smiled. I never thought I would be so attracted to a TS , but as time went on, we became very attracted to one another, at least that’s what I thought.
I knew it was her job to get clients to spend money watching her online but it always seemed we were having a good time talking online, sharing photos, and even pretending to have sex as we watched each other cam-to-cam and jerked off. We did chat a few times on the phone, but we tended to stick with the internet which was less expensive and being able to see each other was great too.
I wanted to be with her and even though I had never been with a TS, it soon became apparent that we needed to try to meet face to face, but she was so far away. Wanting to be with her had becoming an obsession, and had reached the point that we both wanted to meet. The problem was that she lived in the Philippines and she didn’t have a passport to travel. I considered traveling to see her, but it was more than a 14 hour plane trip and it would be expensive.
I had to consider if the obsession was worth the money and time, especially if it was only a sexual fixation. However, the wanting to be with her eventually had me risk. After buying the tickets, I was excited but then started to have an uneasy feelings, not sure if I should actually go through with it.
I was nervous, but I had the means to go through with it now, and when I broke the news to her, she was at first not exactly sure I was coming. When she realized I would actually be coming in the next few weeks, she seemed to become very excited to have me visit, which made me super nervous.
I arranged to only stay a few days just in case it didn’t work out, and as we continues to talk and play online cam-to-cam, we both looked forward to the day when I would be flying out.
The days went by quickly as we talked about what we would do when I finally got there, and I think Nicole continued to question whether I was actually going to come see her, but when the day finally came around for me to fly to the Philippines, she was very excited.
It was going to be a long flight, and I did have a brief layover in Hawaii before continuing to Angeles City in the Philippines, but finally after 14 plus hours, I was there. As I stepped off the plane, I was directed through customs and eventually made my way to baggage claim and then out to ground transportation where we had decided to meet up.
As I walked toward passenger pick up, I worried whether she would be there or if I was going to be on my own, but as I proceeded toward the people waiting to meet other people, Nicole and I made eye contact. She looked just as she did online and as I walked toward her, she had a big smile as I approached.
She was wearing a white top and a short little skirt, and her smile immediately made me smile. As I walked up to her I said, “Hi, Nicole?” Nodding her head, she immediately hugged me and kissed me on the cheek. We quickly continued out of the airport and guiding me toward a taxi that was waiting, we headed off to the hotel where I had made reservations. Nicole told the driver drive in Filipino, as we settled into the backseat.
Nicole snuggled up to me and said in broken English she was glad that I came to see her. Holding her too, I was nervous being a strange place, and as we got on the highway heading into town, Nicole told me it wasn’t going to be a long drive. I remember her asking me what I wanted to do and see, I didn’t know what to say.
As we looked at each other, Nicole started rubbing my leg, and as she felt my chest, she leaned up and asked, “Are you happy to see me?”
I was hesitant, like I said, I had never been with a transsexual but as I nodded and pulled her close, she leaned up, and we kissed. I tried to think that she actually was a girl and it wasn’t hard to do, and it was nice to finally be with her.
Nicole now casually put her hand between my legs, as we kissed again, which made me feel a little more at ease, thinking that yea, we were going to have a great time.
Nicole tried to point out a few sites from time to time along the way and as we got off the highway, we ended up in front of a hotel. As we stopped, Nicole said, “We're here,” and after paying the cabbie, we quickly got out of the taxi, and hurried inside.
At the front desk, she quickly got our room key and as we headed up the elevator, she continued to hold me. There were other people in elevator as we went up to our room and feeling they were watching us, we didn’t do anything. However, as we entered our room, we both looked around, and eventually moving toward the bed, we both sat on the edge. Leaning into me, Nicole kissed me and smiling we immediately started feeling on each other as we made out, but suddenly Nicole then stopped us.
Maybe a little nervous herself, she asked if I wanted her to show me around town a little. I said, “It’s up to you,” and as we continued to make out on the edge of the bed, Nicole smiled and told me again how glad she was that I came to see her. Leaning into me again we kissed as passionately and deeply as we had ever fantasized about doing online, and as we continued to feel on each other and kiss, I tried to take her clothes off.
Her body felt as good as I had imagined and she seemed to enjoy feeling on me too, and when Nicole started trying to pull my shirt off, I obligingly helped take it over my head. Immediately I took her top off too, and as I went down and suck her neck, I put my hand on her little tit. I was started to get a hard on and feeling her boobs was great. As I gradually move down her chest kissing her, I eventually started tonguing and sucking her hard little nipples.
She gently held my head against her tit, making moaning sound as I continued to fondle her boobs and tongue her nipples. Nicole started trying to grope for my cock, even though I still had my pants on. I wanted her to feel that I was hard and as I stood up, I took her hand and guided her to stand too. She was short so she had to get on her tippy toes as we leaned into each other to kiss.
Nicole soon began to undo my shorts and as she slid them down, and they fall to the floor, she looked down. Adjusting my boxers, I knew she could see my hard on bulging. Smiling, she looked up at me and as we kissed, Nicole reached down to feel my cock. Feeling my hard cock, she went down and mouthed at my cock through my boxers. Looking up at me momentarily, she pulled down my underwear until my cock flopped out.
She again looked up at me smiling and as I watched, she slowly began stroking my cock, eventually taking it in her mouth. It felt so good and as I closed my eyes, I didn’t want her to stop, but she suddenly stood up and kissed me. Smiling, Nicole again tried to move back down to suck my cock, but I stopped her. She asked, “What’s wrong.”
I didn’t say anything but instead simply kissed her and slowly started to inch her little skirt and then pulled her panties down. As she helped pull them down, and they eventually fell to the floor, I had her lay on the bed. Looking at her laying there, smiling as she tried to cover her crotch, I quickly climbed on the bed with her. It was such a turn on feeling her body next to me, and as she put her arms around my neck, we kissed as our bodied rubbed together.
Nicole then pushed me onto my back and as she climbed on top of me, straddling my waist, she said, “I want you in me.”
Smiling back, she leaned over to the nightstand and taking a tube of KY out of her bag, I nervously watching as she reached out. I had had anal sex with a girl before when we were both drunk but feeling her cock rubbed up against my stomach and chest was something totally different.
As she leaned back and we looked at each other, I realized I didn’t have a condom, which worried me. I didn’t know what to do and as she soon leaned back again straddling me and I watched her flip open the tube of KY and squeeze some on her hand, I was nervous. As she reached around herself, and looked at me smiling, I could see she was smearing KY on her tight little hole. My cock was so hard and I wanted to fuck her. When Nicole took hold of my cock again, I continued to worry about not having a condom.
I tried to tell myself it would okay, as she rubbed my cock rubbing from behind with lube. Nicole again leaned forward and as we kissed, she reached into her bag again, I watched as she took out a condom. Smiling with relief as she opened it, she turned around slightly and quickly rolled it on my hard cock. As she turned back around, she softly said, “I am so glad you’re here,” as she leaned forward passionately kissing me.
As Nicole leaned back, she tried to guide my cock, pushing it against her tight little hole as she sat back. I could feel the head of my cock starting to push into her and as I watched her face, I could tell it was hurting. Holding her by her hips, it felt there was some degree of pleasure too as my cock pressed into her.
She continued to slowly try to work my cock into her all the way in and as I reached out taking hold of her boobs now, I told her to relax. Nicole smiled and closing her eyes, she put her hands on my chest as she slowly let my cock slip into her ass.
I was in her all the way and as Nicole gradually started moving up and down, Nicole smiled and leaning forward we kissed briefly. It was so warm in her and as she continued to slowly move up and down again, I could see by her face, she was enjoying it too. I wanted me to cum and feeling Nicole’s hard cock laying on my stomach, I continued to feel on her boobs. I continued to watch her face, and as she leaned forward, my cock glided in and out of her ass more easily as she moved up and down on it.
I tried to thrust my hips up and down too, trying to concentrate on cumming, Nicole stopped. As she leaned forward and our eyes met, she kissed me and said, “I want to take off the condom so I can feel you in me, is that okay.”
I didn’t care right now, I wanted to cum and so I nodded my head in agreement. Nicole smiled and leaning forward again, she let my cock slipped out of her. Quickly pulling the condom off, she again guided my cock into her wet little hole. It went in easily this time and as she again started moving up and down on my cock, I went back to feeling on her tits, which made her smile.
As Nicole rocked back and forth and up and down, I could feel and see her cock bounced against my stomach, which made me even more excited. I want to cum as I tried to match her movements, but now and then she seemed to lean back on my cock relishing the feel of my cock way in her.
At one point, Nicole leaned forward again and kissing me said, “Cum in me, I want to feel you cum in me.”
She rocked back and forth on my cock faster now and as I grabbed her ass, I tried to keep her going as I fucked her. I was close now and as I moved my hands to caress her boobs again, I told her, “Don’t stop.”
Smiling as she kept moving up and down, I moved my hands back down to her ass. Trying to stop her now I tried to hold her down on my cock but just kept moving up and down. Out of breath I said, “I going to cum.
Breathing hard too, Nicole said, “Cum in me.”
As I held her, I pushed my hips up and as she leaned back forcing my cock deep in her ass, my cock started jerking as cum shot inside her. Grabbing her hips, I guided her to move her hips back and forth again. It was obvious that she felt the warmth of my cum inside her because as I looked up at her, Nicole was smiling, and then leaned forward to kiss me. I knew I had cum a lot, and as she leaned forward to kiss me, and I looking down at her cock, I could feel cum dribbling out of her ass.
Kissing her and putting my arms around her neck, my cock quickly went limp and slipped out of her. Nicole slowly lifted off of me and as she laid next to me on the bed, we pulled the covers over us as we continued to kiss and feel on each other.
Eventually she took hold of my cock and in turn I found myself grabbing hers. As I slowly started stroking it, she softly told me that it felt good and pausing, Nicole said, “I want to cum for you.”
As I kept stroking her hard cock, and we kissed, Nicole laid back. She then tried to push my head down obviously wanting me to suck her cock. As I looked up at her, she smiled and continued to push my head down. Hesitantly, I kissed her chest and eventually tonguing and sucking her nipples, trying to delay going down on her. I knew what she wanted, but nervous never having done it before, I looked up at her as I took her cock in my hand.
Nicole lifted the covers slightly and looking down at me she said, “Put it in your mouth, suck it.”
Nervously looking down at her cock, I wanted to try it, but again, no condom. Looking up at her again, Nicole smiled and continued to slowly guide me to suck her cock. As I got close, she stopped me and said, “Are you scared?”
Looking down at her cock, she reached up to her bag and grabbed another condom from her bag. Handing it to me, I quickly opened it, and placing it on the tip of her cock, I rolled it down until it covered her completely. As I started stroking her cock and eventually kissed and mouthed it. She then said, “Go ahead suck it,” as she took hold of it.
Closing my eyes, I took her cock into my mouth. Nicole took hold of my head with both hands and pushing my head down on her hard cock, she forced it into my mouth. I tried to continue to stroke her cock as I sucked her, wanting her to cum, and when she told me how good it felt, I was nervous knowing she was going to cum.
Nicole then pulled my head off her, telling me to stop. As her cock slipped out of my mouth, she took hold of it. Looking up at her, she smiled and asked, “Can I fuck you?”
Looking down at her hard cock, she again pulled me up saying, “I want to be in you.”
Smiling at her, Nicole sat up and as she got on her knees, I watched as she took her hard cock in her hand, stroking it. She then motioned for me to lie on my stomach. Rolling over so I was laying face down, she spread my legs and quickly positioned herself behind me. Rubbing my back and ass, she leaned against me, pressing her cock against my crack.
Leaning back up, Nicole spread my ass cheeks and when she touched my tight little hole, I tighten up and flinched. She told me to relax as she again spread my ass and then she leaned down and putting her face in my crack and pushed her tongue into my ass. It felt good but she soon stopping and leaning against me, she reached over for the KY.
Feeling her cock rubbing against my ass and legs, I nervously glanced back with mixed feeling never having done this before. I started to worry about being fucked, even though I had thought about it and used toys from time to time, I was still apprehensive. Nicole now positioned herself behind me, and hearing her flip open the tube of KY and hearing her squeeze some out in her hand and rubbing it on her cock, I tried to prepare myself.
I was scared as she spread my legs and told me to relax. Spread my ass and dabbed lube on my hole, I tried to relax as she gently pushed a finger in my ass. It made me pull away slightly but as she continued to finger my ass, she again told me to relax as she spread my legs a little more.
She now directed my to get on my knees, and as she help to raise me up on all fours, her cock pressed against me. Rubbing her cock in the crack of my ass, she asked if I was ready. Nodding my head, she leaned forward kissing me on the back. As she continued to rub her cock in my crack, she occasionally pushing the head of her cock against my hole. This caused me to tense up and pull away slightly, worried about her penetrating me.
I had to relax, I wanted to feel her in me and as Nicole pushed on my back telling me to lower myself, she again told me to relax. As I did this I could feel her again trying to push her cock into my ass, and as she started to enter my ass, it was okay t first, but as she pushed further in, it hurt and I rose up. Reaching back, I told her to stop as I pushed her away. Nicole’s cock slip out and she again rubbed my ass and told me to relax and said, “ It’ll only hurt for a little bit.”
I wanted this now and I realized that until her cock was all the way in it would hurt, so I nodded my head and as I put my head down, she again pushed my ass down, making me spread my legs more as she started to push her cock into me again.
The pain of her in me was excruciating and even though I desperately to relax, it caused me to pull away occasionally and when Nicole felt me try to pull away, she immediately held my close and told me to relax.
We didn’t move for a little bit and the pain did subside, but there was still a dull aching as she again pushed her cock in me further, until she was all the way in. Leaning forward, she asked if I was okay as she kissed me on the back. Nodding my head, she slowly started moving her cock in and out of me. It hurt and sometimes the pain made me pull away, but it was bearable and I continually tried to relax as she fucked me.
As she started to really pump my ass, it actually started to feel good, and when she guided me to move back and forth too, it felt so good my cock started to get hard as she fucked me.
I could tell she was going to cum and I wanted her to cum in me and hearing her she breathing becoming more labored as she fucked me, I knew she was close. Suddenly, I felt her stop and as I unknowingly tried to keep moving, she pulled me close and said, “Stop!”
Feeling her cock throbbing inside me as she held me close, I smiled knew she had cum in me. As she tried to fuck me again, out of breath she pushed me flat on my stomach and shoved her cock deep in me one last time. It hurt but then Nikki slowly pulled out and as she knelt behind me, she pulled to condom off, threw it aside and then milked the last few drops of cum out on my ass.
Nicole then leaned forward, pressing her cock against my ass as she rubbed my back. Leaning back up, she started rubbing my ass cheeks, gently spread them wanting to see my gapping hole. Smiling I shifted slightly as she gently pressed her finger against my hole. I could feel lube had started to seep out, and seeing this must have turned Nicole on, because she suddenly pushed her cock back in my ass.
It surprised me, “What is she doing,” I thought, as she leaned into me.
It felt good but she didn’t have the condom on anymore. I tried to turn but after pushing her cock deep in me one last time, she quickly took it out. As she laid on me, pressing her cock against me I was scared. Nicole kissed me on the back again and said whispered how glad she was that I came to see her. Turning onto my side as she lay next to me, I looked at her puzzled.
Eventually held each other, Nicole suggested that we take a shower. I continued to worry about what she had just done but let her lead me toward the shower. I desperately tried not to worry about it and as she bent over to turn on the shower, I grabbed her ass as she tested the temperature. She then reached around taking hold of my cock and turning, we kissed. It felt good to be with her and as she turned back around, and got into the shower, Nicole motioned for me to follow her. As soon as I got in, I immediately tried cleaning my ass, fingering it with soap and water, hoping it was okay.
Realizing there was nothing I could do now, I innocently leaned into her, pressing my cock against her and reaching around, I grabbed cock. Pushing her ass against me, I pulled her close as she leaned her head back into the water. Nicole then turned around and as she did, I then reached around her feeling her boobs and pushing my cock in the crack of her ass as she leaned into the water to get wet. We had fun soaping each other up and as we rinsed off, we started to make out in the shower, kissing and feeling each other’s cocks.
It wasn’t long before we were back in bed making out again. Having me laying on my back, she climbed on top of me and after kissing for a while, she turned until she was straddling me, facing away though. “What was she doing,” I thought, but as she back up, putting her ass in my face.
Seeing her little butt hole so close made me nervous, thinking she wanted me to tongue her ass, and not wanting her to sit on my face, I put my hands on the backs of her thighs. Nicole turned slightly and after smiling, she leaned forward sucking my cock. As she backup further, I realized she must want to be in a 69, and so I grab her flaccid little cock and tried to suck her too.
She moved back a little more allowing me to eventually take her cock in my mouth too. As I sucked her cock, I spread and rubbed her ass cheeks, and thought, “I want to fuck you again.”
It was getting late, and soon we ended up laying in bed together and as we held each other, we fell asleep.
The next few days, Nikki took me around, showing me a few sites but we always ended up back at my hotel room, in bed. We did end up having sex without condoms, which to this day still worries me but in the heat of the moment, it was so hot to not only feel her in me, but to be in her too.
I was only able to stay in the Philippines a few days and yea it was hard to leave, but I had a return ticket. The experience was more than I had expected and she did try to keep me from leaving.
Nicole was really pretty and I learned a lot. We continued to chat online, but I never did visit her again. We eventually lost contact, I don’t know why, but every time I see pictures of her, I ended up thinking about her, wanting to be with her again.
