While on holiday in Thailand just last week with my wife and our friends, I had three massages.
Each massage was a double one in a bamboo hut on the beach with my wife less than two feet away also having a massage.
There were several massage therapy facilities along our two-kilometer stretch of beach, most of which were connected to hotels or bars. We decided on the one that was the furthest from our hotel because it appeared a little more private and had a nice bar and BBQ nearby.
We decided on a basic Thai massage for the first treatment, which would last an hour. My wife had a boy who was in training and appeared to be around eighteen, and I had a woman in her mid-twenties as my masseur.
I wore shorts over my trunks and was instructed to dispense with the shorts my wife wore in a bikini.
For the first half hour, we both had to lie on our stomachs. The masseuse used Thai to communicate with each other, and it appeared like she was giving the man directions, but I could not understand Thai, so it was only a guess.
Although the shack had a thatched roof, the sides were completely open, and after the wonderful full body massage, we were told to flip over onto our backs for thirty minutes. Before they continued, they draped a light muslin cloth over our faces to help us rest and shield our eyes from the sun.
As she massaged my thighs, the masseuse began on my feet and worked her way up my legs to my groin, rolling each side of my trunks up even higher, even though they were already short.
A small stroke on my cock occurred as she was doing it, and I assumed it was a slip of the hand rather than a grope until it occurred a few more times. Then I felt a finger inside my trunks moving along the side of my cock, causing him to quiver once again. I accepted it as an error of judgement, let it go, and relished the moment.
I told my wife about it later, and she told me that she had gone through a similar thing where her partner touched her nipples a couple of times and inserted a finger or two inside her bikini bra.
As two oldies, we were flattered and joked about it, hoping they had a little fun.
We went for a beer and some lunch, and since it was such a beautiful day, we decided to have another massage even though the first one was not scheduled. This time, I was only wearing loose-fitting swim shorts and no trunks.
We decided to have a Thai oil massage this time, and since we were in the same shack, we were a foot or so away. This time, we had a different masseuse than the last time; I had a slightly older woman, and my wife had the same woman who had massaged me the first time.
Although the back massage was unremarkable, the oils were beautiful and provided us with a nice feeling. This time, I was worried that my cock would slide out of one of my shorts' legs because there was only a mesh liner to prevent it.
It became a little cheeky after I flipped onto my back. The masseuse moved past my calves and feet to work her way up onto my thighs, rolling the loose legs of my shorts all the way up into my groin before working on my thigh muscles.
The muslin cloth covered my face once more, but this time I moved it to see underneath it and observe what was happening; my wife had done the same.
Both women laughed a little as the woman gave my cock a noticeable stroke as she rolled up the cloth of my shorts, making me jump.
There was a lot of conversation and laughter between them until they finished exactly on the hour mark. As the massage continued, I felt the woman's fingers repeatedly encroach on my shorts and stroke and squeeze my cock and balls, causing them to thicken and swell and creating a bulge in my shorts.
My wife acknowledged that she witnessed everything and was excited and turned on by it when we talked about the massage later. This was followed by some frantic making love in our hotel suite.
My wife acknowledged that she was wet during her massage because a finger had been put into her pussy and slipped into her trousers. Even though it was the first time she had ever been fingered by a woman, she still found it enjoyable.
We went for the third time the day before our flight home; this time, it was my 65th birthday, and our friends joined us for the vacation.
We waited until nearly dusk before scheduling our massage because we had already had a long day of drinking.
Since we were the only two couples there, we were given separate shacks at either end of the six shacks to provide total solitude.
We were being led to our cabin and getting our feet washed when I noticed John, our friend, talking to the woman who seemed to be in charge. After some money was exchanged, they both turned to face us with broad smiles.
A mature woman in her fifties and another attractive woman in her mid-twenties took the place of the women who had just bathed our feet, who would typically be the ones to provide the massage.
After washing and drying our feet, we were instructed to lie on our stomachs and gaze out at the sea and the setting sun while I wore the same swimming shorts as before and my wife another bikini.
I was assuming my role. I watched the older woman start to take off my wife's bikini top; she was lying on it, so her breasts were hidden.
In contrast to earlier days when the masseur began with my feet and worked her way up, the younger woman began with my shoulders.
This woman was amazing. As with prior visits, she used the warming oils to proceed down my body, relieving the stress from my neck, shoulders, and back with her kind yet effective hands.
She urged me to lift my rear as she got to my waist, and I obeyed. Perhaps it was the drink or curiosity, but I let her take my swimming shorts down. My wife did not discover until later that my shorts were entirely taken off and laid out on a chair next to the shack, face down
My cock was underneath me when I lowered myself again, but I was not sure if the masseuse could see it.
I was requested to turn over after she spent a long time focusing on my thoughts and ass before moving on to my calves and feet.
This was going to be challenging. I was given a very thin towel—more like a flannel—that barely covered my groin; I spread it across my pubic region and turned over at the same moment as my wife. I was not erect, but I was not limp either.
After giving me a quick smile and mouthing the words "Happy Birthday", my wife lay down with a muslin cloth covering her face.
The younger masseuse returned to my wife, whose bikini top was now back in place, after the masseurs had switched places.
After a little tweaking, I was able to see my masseuse hands and the bulge in the flannel covering my developing cock through the muslin cloth that had been covering my face.
She began by gently sliding my feet and ankles up my legs towards my trouble spot, which kept getting bigger. The woman was constantly talking and laughing while I laid still, wondering what they might have planned.
Her palms or knuckles were constantly prodding my cock as she worked on my thighs; each touch or nudge caused him to grow somewhat further, rendering the flannel nearly useless because I could see the majority of my cock. I was aware that the woman's perspective was likely superior.
He pointed up at the sky, my cock rising like a flagpole with a white flannel on top.
It took me a bit to understand that she was actually cupping and massaging my balls because I was so focused on watching my cock rise.
I was nude with a Thai masseuse, holding my balls in one hand and my cock in the other, and the warming oils made the situation quite pleasurable. There was more laughter and talking, and then there was a gasp as the flannel was whipped off.
I turned to face my wife, who was so at ease and content that she was unaware of what was happening. I thought I heard a faint grunt as she slept during her massage.
While the elder woman worked on my wife, there was another shift in roles, with the younger woman swiftly taking up her predecessor's hands.
I wanted to see what was happening to me, so I yanked the muslin away from my face. My masseuse had stretched her legs wide apart to take up her position, and she was kneeling between them.
Her lubricated palm glided smoothly up and down my entire length, which was now nine inches long, as she continued to work on my thigh, balls, and fully erect cock, wanking it tenderly.
Her expression was one of pure satisfaction as she relished her authority over me and I was left with no choice but to savour my gift.
My wife was startled awake by my nudge, which caused her muslin to come loose. She looked down to see the woman between my legs lower her head and begin licking up and down my shaft while still wanking me and cupping my balls.
My wife gave me a big smile in return, but there was a look in her eyes that told me something was not quite right.
At that moment, I began to believe that I was either extremely fortunate or that I was being set up. The sun was rapidly lowering, and the fairy lights beneath the shack's roof came on, adding to the scene's beauty and sensuality.
I could not imagine how delighted my wife would be to watch another lady licking my cock, which was already sticky with pre-cum, making the tip sparkle. My mind was racing.
It was an amazing experience as she licked off the sticky sperm, but it was only made better when she put her lips around my pole and began to suck me in a way that had never been done before.
My world started to fall apart as I looked down at this woman with a gorgeous smile and a perfect pert set of tits, my cock in her mouth and an erection nearly as large as mine between her legs while I poured my fluids down her or his throat. The blowjob was amazing, and the sensation was almost making me want to shoot my load.
She or he took every drop while my wife sat up laughing uncontrollably and our guests arrived laughing uncontrollably. There was nothing I could do to halt what was happening. Our buddies had been observing from a distance, and I was not even bothered that they saw my cock for the first time and saw me get a blowjob.
I was the target of mockery. I should have had a suspicion when I noticed the money transaction, but this was not what I anticipated.
After giving me my shorts, the masseuse grinned and left, receiving praise from my buddies.
Despite being embarrassed, I was quite pleased with the quality of the massage and blowjob, even though it was performed by a crossdresser with a large cock. I hastily put on my shorts.
Although I could see the humorous side of the situation, I felt a little ashamed that I had fallen for such a simple setup. I was eager to return to the hotel, take a shower, and get my cock, and the idea of a crossdresser licking it out of my head.
As we walked back to our hotel my buddy's wife walked with me and in a calm voice commented on the size of my cock and said that she would love to have me use it in her.
I was shocked at her comments but she assured me she would give me a blowjob to remember if we had some time alone.