Pool Tranny

I was visiting relatives on a weekend vacation a few months ago and because there were so many of us, some of us had to stay in hotels near by. After first checking in over at the house, I headed to the hotel where I had reservations. It was a modest hotel with two floors, a courtyard with a pool, and the rooms all had outside entrances, which I liked.

As I headed toward the office, I could see the pool, and immediately thought about taking a swim after checking in. After getting my room key, I decided to cut through the pool area. It was a large pool for a hotel, there were plenty of chairs, and it looked very clean and inviting.

Casually looking around, there were only a few people, and as I continued toward the other end where my room was, there was an attractive younger lady that caught my eye. She was laying on one of the loungers by the gate where I was headed and as I went by, it was hard to not check her out.

She had big boobs that seemed to almost spill out of her light blue bikini top, a few tattoos on her arms, and it looked like she had one on her hip. Catching myself staring as she leaned up on one of her elbows, I smiled, and as she looked over her sunglasses, she smiled back and then seductively, licked her lips.

It was obvious that she was teasing me, and feeling a little embarrassed, I inconspicuously looked away and reached for the gate. As I pushed it open, I curiously looked back as the gate closed. She had laid back again, and as I continued to check her out, she seemed to be smiling, which made me smile too.

She was definitely hot and immediately I told myself to go back down. As I convinced myself to go down to the pool, if for no other reason to see if she’d still be there, I told myself, “It had been a long drive and that I should go for a swim.”

Immediately putting on my swimsuit, I innocently headed to the pool for a swim. Yea, I hoped she’d still be there, but as I continued, I told myself it wasn’t likely. However, as I opened the gate and made my way into the pool area, there she was. She had moved over to sit by the steps in the shallow end, and as I threw my towel down on a chair, I quickly went over to the edge of the pool.

As we smiled at each other from across the pool, I immediately jumped in and swam around. Eventually, I made my way over to the shallow end where she was sitting, and not wanting to be too obvious that I was interested I tried not to look her way. However, as I put my arm over the edge of the pool, she suddenly said, “Hi.”

Turning and facing her, I smiled and as I lifted myself up, out of the pool slightly I simply replied, “Hi,” too.

She really was sexy looking and when we didn’t say anything for a moment, I casually said, “This is nice.”

As we continued to look at each other, she nodded, and then as she seductively looked over her sunglasses, she casually introduced herself saying, “I’m Eva.”

She had a slight accent that sounded like it was either Spanish or Asian, in either case, her broken English was intriguing. Smiling, I leaned over the edge of the pool toward her, and as I reached out to shake her hand, she smiled too. She was kind of tall and big for a woman, not fat, just big, and being she was very attractive, and had great boobs, it was easy to look past it.

She was still wearing the light blue bikini from before and as she leaned toward me, I couldn’t help but stare at her cleavage. Eva looked to be in her late twenties or early thirties, and even though she was wearing a lot of makeup and fake eyelashes, she was still very attractive. She had sandy blonde, shoulder length hair, a few tattoos, and she had great lips. As I continued to check her out while we chatted, I started to get a hard-on thinking about being with her, but at the same time I told myself that she’d never consider it, being I was much older than her.

Yea, she was attractive but, there was something about her that I just couldn’t put my finger on. As she stood up and moved back over to her lounge chair, I couldn’t help but look at her ass and legs, especially when she happened to reach around, pulling her bikini bottoms out of her ass.

She did have a big butt, not huge, and being she was kind of tall, her legs were big too. I really wanted to see more, and as I lifted up out of the water hoping to catch a glimpse of her crotch, I ended up staring intently as she sat down. I desperately looked as she swung her legs onto the lounger and laid back.

Shifting herself around as she got comfortable, I could see the front of her bikini bottoms pushed out a little. “Wow,” I thought, “ she’s got a plump little pussy.

Not wanting to get caught staring again, I immediately looked up as she crossed her legs. Seeing her smiling, I felt a little embarrassed and so I slipped back down into the water and blowing bubbles, I swam away.

We didn’t talk with each other the rest of the time, and feeling nothing was probably going to happen, I decided to leave. As I swam over to the ladder in the deep end, giving my hard-on a little time to subside, I eventually climbed out. Quickly grabbing my towel and wrapping it around my waist, I looked over at her. She smiled as she looked my way, and then as she laid back, she casually grabbed her tits, adjusting her bikini top.

Smiling as I walked around the pool to leave, I innocently said, “It was nice to meet you.”

Eva leaned over onto her one elbow and as she looked at me, she smiled and in her accent said, “Why don’t you come up to my room.”

This caused me to pause just as I was opening the gate to leave and as I looked over at her, Eva pointed and said, “I’m in room 204.”

Looking over to where she was pointing, she said, “If you want to,” which made me quickly look back at her.

She was smiling questioningly and as I nodded my head and closed the gate, I turned and headed back to my room. On my way, I curiously thought, “Maybe she is interested,” which made me seriously think about it.

I definitely wanted to be with her and the thought of it was exciting, especially since she was obviously much younger than me, but it made me nervous too.

In the shower, as I rinsed off, and the water beat down on me, I found myself closing my eyes and jerking off, as I thought about her. Immediately deciding to go see if she was truly interested, I stopped and quickly got out of the shower. Wanting it to be as casual as possible, I threw on a short sleeve button down shirt and a pair of shorts, all the time telling myself to have an open mind and to not expect anything to happen, but of course I hoped something might.

Nervously, I went over to her room, and as I knocked and looked around, she opened the door. Smiling at me as she opened the door wide, I couldn’t help but smile back. She looked great, which made me even more nervous but as we smiled at each other, she said, “Hi, come on in.”

She was wearing dark red lipstick, big hoop earrings and as I stepped inside, I couldn’t help but look down at her chest. She had on a long sleeve, white blouse that was so sheer it was see-through, and as I continued to stare, I could see her sheer white bra too. Her blouse draped down to her thighs, but I could see she was wearing some black leggings.

Eva was so attractive and as I looked back up, I could see she had caught me staring, but as we looked at each other her big smile made me enthusiastically smile back and say, “Hi.”

As I moved into the room and looked around she said, “Go ahead and have a seat.”

Casually making my way over to the bed, I sat on the end and as I looked over at her, she closed the door. Continuing to look at her as she walked toward me, I couldn’t help but look at her chest, wanting to see her tits, and as I continued to glance down, I could faintly see her nipple through her blouse and bra.

Realizing I was staring, I immediately looked back up. She smiled and said, “It’s nice to see you again,” and as she sat next to me, there was an awkward moment. I sensed we were both a little nervous and as we both search for what to say, Eva said, “You know, I was just about to go down to the lounge for a drink,” and then she suggested we could go down for drinks.

I couldn’t have agreed more, because with both of us feeling a little nervous and a few drinks would definitely help and as we both stood up and quickly left. We ended up chatting as we headed down to the bar. As we went in, it was kind of dark, there was some music playing, and there were some people sitting at the bar.

As we sat across from each other in one of the booths, I found myself looking around. It did feel that people were watching us and as we started talking, our waitress came over. As she took our order, she seemed to look at Eva questioningly, and then when she looked at me, she seemed to look at me a little confused. She then didn’t look at either of us directly and then after taking our order, she gave me a cautious smile and said she’d be right back.

Curiously looking at the waitress as she walked away, I eventually turned back when Eva asked if everything was okay. Smiling as I looked at her I nodded and as we started to talk, I forgot what had just transpired.

We ended up having a couple drinks, maybe it was three, I really can’t remember, but as the bar started to get more crowded, Eva reached across the table and as I took her hand, she suggested we go back to her room.

I was definitely feeling no pain, and not wanting to get too drunk, I felt it was probably a good idea. As we headed back to her room, we ended up joking with each other, and bumping against each other, eventually hugging, and then holding hands. I nervously thought about making a move, but as we got to her room and she started to open the door I said, “I had a good time.”

Turning as she opened the door, she looked at me and then taking my hand she asked, “Do you want to come in for a little bit?”

As I looked down at us holding hands, I suddenly started having second thoughts, but then seeing I was nervous, Eva said, “Come on,” pulling on my hand.

Looking up and smiling, we went inside, and as we moved over to the bed, the door slammed shut. I nervously stood there and then as I sat on the end of the bed, Eva stood in front of me. Looking up at her, she smiled and looking at each other, Eva suddenly leaned forward and gave me a kiss.

Smiling at each other, Eva then subtly pushed me onto my back and then laid on top of me. As we again kissed, I instinctively reached up, grabbing her boobs. They really were firm and as our tongues started to tangle, she pressed against me. She smelled great, but then suddenly, she leaned up, and smiling she asked, “Do you have a hard on?”

Shyly smiling at her, she reached down and as she felt on my cock, and rubbed it through my pants, she smiled. Eva then stood up and smiling said, “I’ll be right back.”

As she walked toward the bathroom and closed the door, I started to worry and thought, “What just happened?”

Sitting up as I waited impatiently for her to come back, I quickly adjusted my shorts, and then the bathroom door open. Turning as Eva walked over, I could see she had taken off her leggings, and as she stood in front of me, I immediately looked down at her chest. Her blouse was only button once about half way down and seeing she had taken off her bra, I looked up at her. As our eyes met, she smiled and asked, “What do you think?”

Smiling back, I immediately looked down at her tits, and seeing her little nipples, I instantly looked back up. I was starting to get hard and seeing that Eva had a big smile, I found myself looking back down again. I hoped I might see her pussy through her blouse, but seeing she was wearing lacy sheer white panties, I again looked back up at her.

Eva then leaned forward and as I looked down her blouse, she reached down and felt on my crotch. I was definitely starting to get hard and as we looked at each other she smiled and said, “I’m thinking you like it.”

Smiling, I again stared at her tits, and as she continued to feel on my cock, she immediately started to unbutton my shorts. As she started to pull them down, I got nervous, but when she stood back up and said, “I think I need to show you something,” I ended up looking at her, smiling curiously.

Eva casually unbuttoned her blouse and as she pulled it apart showing me her tits, I found myself reaching out to feel them. She had small nipples and as I looked closer, I could see a couple small scars under her tits, which I figured was from a boob job. As she let her blouse fall off her shoulder, she stepped back, letting it fall to the floor as we looked at each other.

Smiling, she now reached down and as she started to feel on her pussy, I instinctively looked down too. Eva had started feeling on her pussy, and as she pulled on her panties, I watched intently as she started to pull them to one side. Looking up at her briefly, she had a serious look and when I looked back down wanting to see her pussy, I couldn’t be it, she had a dick!

I was in shock and as I again looked up at her confused i thought,“Oh my god,”

She had a serious look and as I instinctively looked back down and seeing Eva contin I didn’t know what to say or do and when she asked, “Do you like it,” I found myself sheepishly smiling as I looked up at her.

Eva was still smiling, and when I curiously looked back down at her cock again she asked, “Have you ever been with a tranny?”

I never had and it was probably obvious I was a little scared and as I looked back at her again she asked, “You wanta try it?”

It was definitely a turn on and yea, I had thought about it before, and even though I was a little fucked up, her being really attractive, it still made me nervous. Eva then casually leaned down and as she felt on my crotch she said, “I’m thinking you like it,” and then seeing me smiling shyly she said, “Let’s give it a try.”

Eva then undid my shorts and as she started pulling them down, I smiled as I nervously lifted my ass up a little, letting her get them down a little further. As she got them over my feet and cast them aside, I watched as she reached in my boxers and pulled out my cock.

Looking up at me as she started rubbing it, I couldn’t believe what was happening, and as we looked at each other she asked, “How does that feel?”

It definitely did feel good and as I smiled sheepishly, she inched my boxers down a little more, and then she went down and took my cock in her mouth. Laying back and closing my eyes, I tried to not think about a guy sucking my cock, and instead tried to distance my thoughts. Suddenly, she stopped and after pulling my shorts down the rest of the way, and dropped them to the floor she looked at me and said, “Move up.”

Smiling, I moved up and as I laid in the middle of the bed, I watched as Eva pulled off her panties and then she climbed on the bed too. Moving up and kneeling next to me, she immediately started pulling and rubbing her cock. Curiously looking down at it, I could see she wasn’t hard and as I looked up at her she asked, “What do you think?”

Nervously looking up at her as she held her cock toward my face, I smiled. I wanted to but, I was scared. I had never done it before and as I continued to look at her, she leaned toward me and said, “Close your eyes.”

Nervously looking down at her cock, I smiled and closing my eyes, Eva said, “Open your mouth,” as she inched closer.

I was hesitant but when Eva touched the head of her cock against my lips, I apprehensively open my mouth. Putting her cock in my mouth as she leaned forward, I pulled away slightly. “What am I doing,” I thought.

I was scared about having a cook in my mouth, and when she put her other hand on the back of my head and pulled me closer, she told me to relax. Eva now tried to move her cock in and out of my mouth, as she moved my head back and forth. Opening my eyes, I started to worry that she might cum, but I didn’t know what to do. Eva then let go of my head and reaching down she started feeling my cock and fondling my balls. I had a hard-on and as she started stroking my cock, I laid back, letting her cock dropout of my mouth. Looking at each other Eva said, “I wanta fuck you.”

Letting her cock slip out of my mouth, I pulled away slightly and as I laid back, she reached down between my legs and touched my butt hole. Eva then suddenly turned me on the bed, and as I looked at her I thought, “What is she doing?”

Eva moved until she was kneeling in front of me, and as she lifted both my legs up toward my head and rocked them forward, I could see her looking at my butt hole. Moving down and grabbing my legs behind my knees, she went down and started licking my butt hole. “Oh my god,” I thought and as I grabbed my one leg, I could feel her trying to push her tongue into me.

It made me pull away and as she looked at me, Eva asking, “What’s wrong.”

It really just surprised me and as I looked at her, I couldn’t help but smile. Eva again held my legs up and after tonguing my butt hole again, she suddenly stopped and spitting on it. Looking down as she dabbed my hole and smeared her spit around, I immediately looked at her rock hard cock as she held it . It seemed to have a weird little bend in it and as I looked at her, she again leaned down.

As she put her hands behind my knees and pushed my legs forward, she again spit on my hole. Leaning back up, she started teasing the head of her cock against my tight little hole, as she held my legs up with her other hand. I tried to help her by grabbing my legs, feeling on my cock as I watched her guide her cock against my hole. Pushing into me now as she leaned forward Eva said, “I’m going to put my dick in you,” and then whispered, “Look at me.”

It didn’t hurt right away but as she pushed into me more the pain made me push on her stomach and ask her to stop. Eva leaned down and seductively said, “Relax.”

Leaning forward, we ended up kissing and as she slowly pushed into me some more, I couldn’t help but groan and moan. Eva then leaned back and again told me to look at her as she pushed into more.

She was in me now, it hurt and as I continued to push on her stomach, she leaned forward again, holding my legs forward with her elbows. As we kissed again, Eva started to slowly move her cock in Nd out of me, fucking me. I continued to moan slightly and as she leaned back and watched her cock going in and out of me, she suddenly pulled out and said, “I want you to fuck me.”

Telling me to sit up, Eva got on all fours next to me. Quickly getting behind her, Eva reached back, and as she spread her ass I thought, “I wanta fuck you.”

She only had a smattering of hair in her crack and as she continued to spread her ass for me, her hole started to gape. I couldn’t believe what I was seeing and as she put her head down on a pillow, she licked her hand and then fingered her ass. I was hesitant about doing it and when Eva told me to spit on it, I got really nervous, but did what she said.

Eva then reached back and pulling me closer, she grabbed my cock.watching her as she guided my cock against her hole, I pushed into her. Eva rocked backed and as my cock pushed into her, she put her head down on the pillow and said, “Oh shit!”

Pushing into her more, her ass seemed to swallow my cock, drawing it all the way, and as I started to fuck her, she leaned up, spreading her ass as she rocked back and forth. It felt good, and seeing my cock going in and out of her, I instinctively grabbed her hips and tried to focus, wanting to cum.

Eva suddenly now reached back and pushing me to stop, she pulled away. As my cock slipped out, and she rolled to her side, I was confused. Looking at each other as Eva got on her knees she said, “I wanta fuck you.”

Immediately, Eva made me lay on my back again and quickly positioned herself in front of me. Smiling, she told me to relax and as she spread my legs and pushed my feet toward me, I instinctively grabbed my legs. Eva now took one of the pillows and as she pushed my legs up more, she tucked it under my ass.

Watching her as she looked down at my butt hole as she continued to hold my legs up, she smiled and again leaned down and spit on my butt hole.

I knew what was coming and as she smeared it around a little, I laid back. However, when Eva grabbed another pillow and pushed my legs forward again, I looked up as she shoved it under me.

Letting my legs go now, she smiled and as she toyed with my hole for a second, she spit on her hand and started rubbing her cock. Eva now told me to relax and as we looked at each other, I nodded as she leaning forward. Again holding my feet and pushing them forward, she spit on my butt hole and immediately started rubbed her cock against my tight little hole.

In anticipation of her trying to fuck me again, I laid back and as she used her arm to hold my legs up by her elbows, I tried to relax. Eva immediately started to push her cock against my hole, and then leaning into me, she said, “Oh fuck yea.”

It really hurt and pushing her to stop, I leaned up trying to pull away. Looking at me, Eva leaned forward and simply said, “Relax.”

Nodding my head, I again laid back, desperately trying to relax as she pushed her cock in me. It still hurt, but she was in me and as I instinctively reached up and pushed on her stomach, I asked her to go slow. Eva then leaned forward and as she let go of my legs, she smiled and then kissed me as she gradually started fucking me.

Eva then leaned back and as she said, “Oh, Shit!” I glanced down.

She was watching her cock going in and out of me, and then leaning forward again, we again kissed. It started to feel good as she moved her cock in and out of me, and when we kissed again Eva said, Oh, Fuck, I’m going to cum.”

Laying back now, trying to relax as she fucked me a little faster, she suddenly pushed deep into me. It hurt and pulling away, I reached up and pushed her to stop. Eva then told to me stop and as she held me still, I felt her cock jerking inside me. Eva was breathing hard and as she started to move her cock in and out of me, I knew she had cum inside me.

Eva now pulled out and as I watched, she continued to jerk off, obviously enjoying the feeling. Seeing her squeeze out the last little of cum on my thigh, I suddenly feeling of concern came over me, realizing I had just let her cum in me.

Smiling, Eva let her cock lay on my stomach and as she sat back on her knees, she reached down, tapping my wet little hole. Eva then said, “Push it out,” as she tried to coax my ass to relax. Embarrassed, I tried to clinch my cheeks, but she wanted to see her cum oozing out of me, and as she continued, cum eventually did start to seep out of me.

Leaning toward me smiling, we kissed and then as she laid next to me, she took hold of my cock and started to try to jerk me off. Looking at me as I layer back, she asked, “Do you want to cum?”

Yea, I wanted to cum, but I was nervous too, and as I naively nodded and smiled, I laid back. Closing my eyes as she continued to jerk me off, I concentrated.

Bucking my hips as I tried to cum, she leaned toward me and said, “Cum for me.”

Reaching down, I took hold of my cock and as I took over, Eva started feeling on my chest and rubbing my stomach. Closing my eyes, trying to focus on cumming as I jerked a little faster, I said, “I’m going to cum.”

Breathing hard as I continued to stroke my cock, I stopped and as I pushed my hips up and cum shot onto my stomach, Eva kissed my chest. It felt good to cum, and when Eva grabbed my cock and milked the last little bit out, she leaned down and licked the head of my cock.

Eva then let go and as we laid there, she pulled the pillow out from under me and as we laid together for a little bit, I could feel cum sliding down my side. Feeling a little uneasy about what just happened, I said, “I think I need to get going.”

Grabbing one of the pillows that was under me and wiping the cum off my stomach, Eva tried to get me to stay. I explained that I had to go over to a relatives. Eventually I got dressed and as I left, we hugged and after a kiss at the door, I left.

I continued to think about her and worry about what happened as I walked back to my room, but there was nothing I could do about it now. Immediately as I went inside, I took off my clothes and heading straight to the bathroom, I sat on the toilet and tried to push out whatever cum was still in me.

I felt so ashamed, “What had I done,” I thought, “why did I do it?”

I eventually realized I need to get over to party, and as I took a quick shower, I finger my ass as I washed up. I was so freaked out but I need to get going to my cousin’s house. I continued to think about what had happened and as I mingled, I felt people knew what I had done, and eventually made up an excuse so I could leave.

Back at my hotel, I hoped I might run into Eva and as I passed through the lobby and looked into the lounge area, there she was. Seeing her made me smile, but she was with another guy and it seemed she was having a good time. As I continued to look her way, Eva eventually turned and when our eyes met, she enthusiastically smiled and gave me a wave. However, her smile soon turned to a looked of concern, realizing I had come looking for her.

I felt so dejected and as she looked away and redirected her attention to this other guy, I turned and left. The rest of the night, I worried about what had happened, thinking that she might have given me a disease, but it was to late now.

The next morning as I left, I went by the pool, hoping Eva might be there. I hoped I could get her number. I wanted to keep in contact with her, but seeing she wasn’t there I found myself looking over to where her rooming the second floor. I thought about going over and knocking, but realized she was probably still with the guy I saw her with at the bar.

I was torn about what to do, I wanted to be with her again, but eventually ended up leaving. Even though I never saw her again, I continue to think about her, wanting to be with her, wanting to feel her in me again.

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