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Introduction:

A true story about my first shemale
My First Shemale

I was living on Maui and had just ended a relationship. I had been surfing a couple of Internet dating sites, when this add popped up. A Hawaiian lady wanted to spend a couple of days on Maui and was looking for someone to show her around. She was visiting her family in Honolulu, although she lived in Los Vegas, and wanted a change in scenery. Everything sounded interesting until the last sentence of her post – “I am a transsexual.” Wow! Did I mention that the first time I saw a shemale on the Internet, my cock almost ripped my pants! I pounded out a response and prayed. Shemales are at the top of my fantasy list.

After a couple of back and fourths, we agreed to meet. There was no missing her when she stepped out of the airport. A full head of shiny black Hawaiian hair, nice face, bronze skin, a tube top jutting out in front with evident nipples and a skirt that went about a third of the way down her thighs. She extruded sexuality! My initial impression was that I had hit the jackpot! Well, I had made some plans to show her around – maybe visit a waterfall and skinny dip in its pool or drive up Haleakala for the view or some off the beaten path excursions that tourists rarely visit. We had hardly gotten into my car when she asked if I knew how to get to Baby Beach. I caught my breath. Baby Beach! I’ll have to tell you readers about Baby Beach. On the south side of the island and east of Kehei is one of the most fabulous beaches in the world – Big Beach. It stretches for nearly a mile with twenty to thirty yards of glistening white sand between palm trees and the ocean. No development mars its setting. There is a nice shore break that is good for body surfing although Big Beach is not a spot for true surfing.

However on the west side is a small cliff with a path winding up and over. If you follow the path and climb over the cliff, you drop into a small secluded beach which we call Baby Beach. Baby Beach is small, much more intimate and backed by brush and small trees. There is also a decent surf break when the swell works its way around. The kicker is that this the only public nude beach on the island.

Well, we made our way down, undressed and put our clothes into my pack and started strolling along the waterline. Only a few persons were visible, some walking around or playing in the water. Outside there was a fairly nice surf break – with six or seven surfers living up to the command “surf naked.”

In spite of all the attractions, my attention didn’t wander much from my companion. She was incredible – Barbarella type boobs at least 38D jutting out without any sag at all and large nipples. Her hips were full and rounded. Of course the piece de resistance was this cock sticking out. It wasn’t huge – maybe four inches in its flaccid state – fairly thin at the tip thickening nicely towards the base. No pubic hair at all! Did we get some reactions! Mostly dropped mouths and gawks. One couple turned away. I saw at least two quick erections on guys, one of which received a hard whack from his partner. We found a slightly private spot and laid out our mats. She immediately got out the suntan lotion. I had worked the lotion into her back, legs, ass, when she rolled onto her back. Those two beautiful breasts had to be protected! I began rubbing the lotion around the outer edges. They were very firm – obviously implants, but no scars or anything out of proportion. As I worked up to the nipple on one side, she began to moan softly. The nipple stiffened nicely. I wanted to put my mouth on it, but saw a nearby couple watching us so just continued to work in the lotion. After both sides were nicely oiled, I moved down to her stomach and legs which also were firm but smooth. Thinking I was finished, I handed her the lotion with the idea that she would do me. “You missed something that if it gets sunburned will stop a lot of fun and games,” she whispered. Although I had never before touched a cock other than my own, I didn’t need much more direction to retrieve the lotion and slather some on her penis and balls. I tell you, the cock was fully functional! It stood at full attention. It seemed to swell more at the base than the tip. Definitely a sight for the neighbors. I realized I was doing something that could get me arrested in most places, but couldn’t stop myself. Finally I gave her the lotion and rolled over for my treatment which was nice and sensual, but she only rubbed my cock enough for the start of an erection. She looked at me and said “we’ll spend some more time on this later.” ‘OK with me,” I thought.

We sun bathed for a while and then body surfed some moderate waves. Deciding we had had enough sun, we moved up into the trees and chatted for a while. I asked her about her family’s reaction to her and learned that transsexuals are not uncommon in Hawaiian culture. They even had some spiritual authority with their pre-contact life. Her family had accepted her without reservation once she made it known that life as a boy was miserable. She had lived as a female for seven years and was happy with the transformation. I asked if she would go further and undertake a sex change operation. She had thought about it, but was undecided. She said that she loved her current sex life and wasn’t sure if she wanted to give it up. She was about sixty percent Hawaiian with both Japanese and Chinese ancestry. I also learned that she had flown to Honolulu for a transsexual beauty pageant. Out of some sixty participants, she had received an honorable mention – somewhere between fourth and tenth. I agreed that she was a beauty.

After a nice seafood dinner in Kehei, I drove to her hotel where she invited me in. We weren’t in the room for three minutes when she said “I like looking at you without clothes better than with those shorts.” I didn’t need any further convincing and stepped out of my shorts. She was still wearing the top and a pair of beach shorts. I worked the top over her head and pulled down the shorts. “Are you up for this?” Wordlessly, I just kneeled down and took her cock in my mouth. This was my intro to cock sucking. It immediately seemed to be a most natural action. I thought that my lips were designed for this. But, after a while, she pulled up and said “let me show you a couple of tricks.” She took my cock and rolled her mouth around the head, with her tongue slivering all over the head. Then she would slide her lips down to the base and suck hard as she pulled back. The one that just about sent me over the edge was when she circled around the tip of my cock, working her tongue around the ridges. She smiled up at me and told me to try again. I kind of copied her – not as smoothly as she did, but I got the idea. Her cock stiffened even harder. The she said “do you want to go further?” I knew what she was asking – did I want it in my ass? I took about three seconds to nod yes. She pulled my rear end around to her head, in a somewhat of a sixty-nine position and started rubbing my asshole. She lubed a finger, swirled it between the ass and perineum and then gently pushed it in. Oh yea, it felt nice. Two fingers and then three. No pain whatsoever. She worked her fingers in and out, while caressing my cock with her other hand. I thought that this could go on forever, but she had other things in mind.

She had me roll over on my back with my ass at the edge of the bed. Holding my legs in the air, she stepped up. I felt a pressure against my asshole, and then it slipped in a bit. As her cock was thin at its end, it was easy for the initial penetration. She pushed in further when it began to hurt. She said “take it easy now,” and just held there. The pain receded. She pushed more – the pain would come and then dissolve. It had become a conflict between pain and pleasure, with the pleasure starting to win. She pushed some more and told me to push back. I thought I would force her out when I pushed, but the reverse happened! Her cock suddenly slipped in until I could feel her stomach on my butt. “My God, you have a tight asshole,” she exclaimed, as she began to shove it in and out. The pain had gone and a sensual feeling of pure pleasure had replaced it. “My God,” I thought, “I’ve been missing this all my life!” She would slide in and out slowly, then pull out all the way and shove it in to the hilt. “How do you like being fucked,” she asked. “Don’t stop!” I sounded just like many of the women to whom I had done the same. As she worked away, she spread some lube on my cock and slid her hand up and down. Wow, pleasure at both ends. I felt her cock pressing against my prostrate and wondered if that would make me cum. I could see drops of precum forming on the tip,

“Let’s try another position,” she said as she pulled out and had me turn over and lie on my stomach with my ass in the air. Her cock slipped easily in. It seemed to penetrate further and filled me up. But I missed the prostrate sensation and I missed seeing her smiling face and wonderful breasts bobbing away as she worked away. So she sat on the bed and had me sit on her lap, facing her and lowering myself onto her cock. This position was fun, as we could kiss and I could suck her nipples. I had to do most of the work though, mostly pivoting my ass and tightening or relaxing my sphincter as I moved around. She said again “you’ve really got the tightest ass I have fucked in a long time. Can I take you home?” It sounded like a good idea.

“Now for your next experience,” she said as she pushed me off. She removed the condom and said “try sucking now.” I took her cock in my mouth, but before I had moved up and down three times, I felt it pulse and a spurt of something hit the back of my throat. Another pulse and another spurt. It was filling up in my mouth so I swallowed. It was a bit sour, but not bad – the first cum in my mouth. I milked her cock until it started to shrink.

We lay there for a while, recovering from all that work! “Now it’s your turn,” she said as she bent oven to my waist and started licking the bottom of my cock. It didn’t take long for it to spring into action. She showed me that she still had a couple of tricks to play. The nicest new one was a flutter of her tongue on the top and head of my cock, while she blew out or breathed in. Soon she pulled a condom over me and we changed positions. I lubed her asshole and pushed my cock in. It slid in until my balls were pressed against her. I was a bit disappointed that it was so loose, as I have had anal experience with other women. I guess this wasn’t her first time! I could tell that I probably wouldn’t come, so pulled out. She finished me off with a nice hand job, with my cum splattering each of us.

Before I put her on her plane back to Honolulu the next day, my tight asshole got two more work-outs. Those two days were two of the most sensual of my life. I have been with a couple of shemale escorts, but neither was even close to that first time.
8 comments

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