After the exciting story “FIrst Time Sex,” where a good friend told me how he was sucked off for the first time by a trans woman, I asked him if anything else might have happened that he wanted to share. As the bottom of the bottle came into view, I jotted down the following story. The hot trans in the photo is Daniela. I suck her off at any time.


After Siem Reap (Cambodia) we crossed the border into Thailand, where my girlfriend and I spent a week on the paradise island of ‘Ko Chang’. I hadn’t told you yet that my girlfriend and I have a fairly open relationship, not that we slept with others, but we did find it horny sometimes to talk openly about our fantasies and she knew I was attracted to trans women. When she asked me if I sometimes fantasized about having sex with them, I colored red and she laughed.

A girl made it clear to us that we could undress.

This led to our next adventure, a blowjob vacation. We had already taken a few fun trips around the island and were looking for something new. Strolling around town we came across signs advertising an ‘Oil massage’ and my friend wanted to try it. Of course I did not say no.
We entered one of those signs, and after agreeing on the price, we were taken to a room with two massage tables.

A girl made it clear to us that we could undress and demurely, with a towel over our bodies, we each laid down on one of the separate massage tables. After a few minutes, a girl came in with a bottle of oil in her hand. The girl at the front desk also came in and explained in stony English that there was a problem; after all, there was only one more girl available.

Unless we wouldn’t mind a ‘girl of the third sex’ massaging my friend, she added somewhat sheepishly. My friend laughed and looked at me with a big grin. ‘Of course not,’ she replied. Slightly later, another girl stepped into the room, looking menacing.

Both girls were beautiful and very slender, the first girl was very small and petite, but had very nice breasts under her top. The trans girl was very feminine, a lot taller than the other girl, but also petite in build. Her breasts, compared to the other girl, were also a lot bigger.

This is my trans sister.

This is my sister,’ said one of the girls about the trans girl. The trans girl was very shy and spoke little or no English. They must have both been around twenty.

The trans girl went to work on my friend, the girl came up behind me and poured oil on my chest. When I looked at my friend, I saw that the trans girl gestured my friend to remove the towel from her breasts.

My friend did not look at me, but without shame pulled the fabric down and released her breasts. My girlfriend had quite large and firm breasts and the trans girl looked on approvingly and then poured oil between her tits, got behind her head and began to slowly massage her.

I closed my eyes, and let the girl do the same to me. The wonderfully warm oil and the gentle kneading of my muscles, even caused me to doze off for a moment. I was awakened from my doze by soft moans. I looked at my girlfriend and saw that the trans girl was massaging my girlfriend’s nice breasts, which she apparently didn’t mind at all; I saw that she was enjoying herself with her eyes closed.

Apparently the ladyboy was also paying abundant attention to her nipples, because they too were standing up stiff and hard. This trans girl may not have spoken English, but she knew what she was doing, because the moans were getting louder and louder. My friend didn’t seem embarrassed by her pleasure.

‘My’ girl now gestured me to turn around on my stomach, and now from my feet up started massaging my legs. I found this quite exciting, especially as I now felt her delicate hands had now advanced to my buttocks and into my groin, right next to my balls… I was getting hornier by the minute.

The trans girl had taken off her top.

I turned my head and saw that my girlfriend was also lying on her stomach, and that her towel was just lying on the floor. She was lying completely naked on the table, and the trans girl had apparently taken off her top as well.

She was really nicely built and had a light skin, for a Thai girl. Her beautiful, large breasts looked natural and swayed to the rhythm of the massage.

I am distracted for a moment by the swaying of those large breasts, then I see that she is now also massaging my friend’s legs, AND that my friend’s thighs were now spread slightly in front of her. The trans girl standing at the foot of the table now had to have a very nice view of my girlfriend’s bare pussy, it occurred to me.

I was getting awfully horny at the thought of my girlfriend just showing her wet slit to a shemale. I could also see that she was reacting, because through the thin fabric of her buttoned-up sarong I could see that she too was getting an erection. The trans woman now openly began to massage her further and higher, up to close to her pussy.

Give me transcock

Meanwhile, the girl now also removed my towel and poured oil on my buttocks. It dripped down along my balls tickling. She started massaging my buttocks, sliding her fingers on either side of my balls all the time. I had to shift because now my own hard pole was getting in the way.

As she stood next to me, she saw that I had a stiff pole. ‘This is nice,’ she whispered in my ear. I nodded and felt her one hand now slide between my buttocks, searching my anus, while with the other she massaged my balls.

I too now felt a finger in my ass.

I looked to the side again and saw that the trans girl was doing the same to my friend. With one hand she was now fingering her from behind her pussy, while with another finger she slowly slid into her anus.

I too now felt a finger in my ass, which had very quickly found my prostate. It made me very excited and I pushed my buttocks up. This gave her room to reach my cock, and she now began to slowly pull me off from between my thighs. My girlfriend too apparently found all this very horny, because I say to her as I push her ass up, so that an oiled finger of the trans girl slid deeper and deeper into her most intimate opening.

I now watched as my blonde friend spread her thighs even further. The trans girl was clearly not unaffected, because her stiff cock had now slid out of her sarong, and my friend was lying there looking at it. A rather large, circumcised cock. My friend lowered her arm a little and turned her head towards me, looking at me.

Then she took the Ladyboys cock in her hand and began to jerk her off. I turned on my back so she could see that I too had a stiff pole. She smiled at me and asked, “Does she like it? I could only nod.

Meanwhile, the girl continued to masturbate me.

My friend meanwhile went even further and unbuttoned the trans’s sarong so that the trans girl was now standing naked next to her. She pulled her up by her cock, to her head and took the trans girl’s penis into her mouth.

She immediately sucked her deep and with slow strokes, watching as I was jerked off by the girl. After a few minutes of enjoying sucking her sex, she stopped and said to the trans girl something I never dreamed she would say. ‘Come inside and fuck me’.

Still lying on her stomach, the Ladyboy climbed onto the table behind her. She leaned on her arms and slid between her thighs. Through the oil, her beautiful cock slid in effortlessly; she began to fuck my friend. My friend, meanwhile, pushed her beautiful buttocks up and kept looking at my cock and the girl’s hand around it. The Thai girl herself watched mesmerized as my friend was fucked by her trans friend.

I was almost there when the young trans and my friend climaxed almost simultaneously. My girlfriend’s orgasm announced itself by moaning louder and louder, meanwhile urging the young trans to fuck her deeper with that cock. Just as she was moaning, the trans also withdrew, put her cock between my girlfriend’s buttocks and in four, five powerful jets she spurted her seed over my girlfriend’s curved back.

This picture became too much for me and I too forcefully squirted my seed straight up, onto my belly and over the hands of the girl who was jerking me off. She rubbed my cum, mixed with oil out over my belly, then smelled it on her hand. Then she turned around and rubbed the trans girl’s seed out over my friend’s back and buttocks.

The trans girl climbed off the table.

The trans girl climbed off the table. Her cock was still stiff and the other girl took her friend’s trunk in her hand and now began to jerk it off in turn. ‘Why don’t you sit down next to it,’ asked my friend who had long since realized what was turning me on that afternoon.

The trans girl was indeed very attractive and now for the first time I had a nice view of her beautiful penis, not too big, but at least about 16 cm long and quite thick. As if in a trance, I sat down on my knees next to the girl, with the trans girl’s tightly erect erection in front of me. ‘Now, it is your time to pay her back,’ the Thai girl said, and she aimed her hard pole at my mouth.

I didn’t know what hit me, but in front of the other two ladies, I gently began to lick under the glans, first tasting my friend. The trans girl leaned back against the table, eyes closed. Then I tasted a pole for the first time and felt her lose moisture.

My girlfriend knelt beside me and said, I too want to thank her, and began to lick the trans girl on the other side of her pole, her erection now between both our mouths.

After some time, with my friend tickling her between her balls and anus, the trans girl began to moan and make thrusting motions in my mouth. Her sister, meanwhile, encouraged her and I tasted everything. It felt so natural, sucking this pole, so delicious, I never expected this on a blowjob vacation.

So intimate, so close, the moans were getting louder, the thrusts were getting faster and I knew what to expect. I felt her balls contract and a full load of fresh seed found its way deep into my throat. She tasted delicious. My own cock was hard again now too.

The girl closed her lips around my sex.

Meanwhile, the Thai girl had also dropped her sarong and all four of us were standing naked in the sweltering heat of the room. She had small breasts, and was super slim, with boyish buttocks. She smilingly grabbed me by my erection and said ‘now, it is my time to suck’. Then she also took me deep into her mouth.

The girl closed her lips around my sex and licked vigorously at my pleasure rod. She put her hand under my belly and an oiled finger slid deep into my anus. As her finger kneaded my prostate, I let myself go and in turn squirted for the second time, this time deep into her little mouth. The little girl swallowed it all.

After recovering for a moment, the two took us to the shower next door, where my friend was lathered and washed by the girl, while the trans girl did the same to me. She pressed herself nicely against me, got a stiff pole again, but I decided to leave it at that. After paying them for a fantastic afternoon of sex, we happily went hand in hand to one of the many bars for a beer.

Thailand was also a very diverse country, that much was now clear.

Love, Hans.
Looking forward to your reactions.

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