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Introduction:

From strap-on dildo to shemale sex. My introduction to anal sex.

My journey into the delights of anal sex began a decade ago. I fantasised about my then wife and I having a threesome with another woman. My wife just thought I wanted to fuck someone else. She couldn’t understand I wanted to see HER with another woman. I even bought a strapon dildo for her to use but she wasn’t interested at all. The toy got filed in a drawer. Sometime later we were making out on the bed when she said she had to go to the toilet. Several minutes later she came back naked wearing the strap-on. “Strip” she demanded. Then I got in the doggy position and had my first anal experience.

I am not embarrassed to say I enjoyed it. She did it once more. I loved being pegged. She was less impressed, mainly because I hadn’t discovered “flushing” so the result was, shall we say, rather messy. After the divorce a couple of years later I discovered a shemale website. I was fascinated by the sight of chicks with dicks. Some looking really attractive. Of course, being porn, these shemales had large cocks which also got my lust working in overdrive. Finally I decided to at least try it. So began my journey for real.

I had worked in Thailand and having returned home I was visiting twice a year to catch up with friends. I was in a place called Nana Plaza and noticed a bar with Ladyboys (Shemales). One looked very fetching. I won’t use names, I will call her “A”. I had done my research and learned about douching (I do it regularly now). Saved the mess experienced after my strap-on adventure. I went back the hotel and flushed the pipes and returned. She was there wearing just a bikini and heels. She grabbed me and asked me to buy her a drink. We went into the bar and sat down. I had a drink in one hand and she pushed the other hand into her crotch. She was already hard and I was too. After our drinks she suggested we go to a short-time hotel in the Plaza. I said I had never. But I suspect she already knew that. “Don’t worry darling I will teach you” she whispered.

I paid the bar fine (B500) and the drinks and off we went. The short-time hotel was B340. The room had a large bed and a bathroom attached. She undressed and so did I. I took in the sight. Obviously enhanced boobs and a rock hard cock about 6”. She sat on the bed against the head board and said “suck my cock”. Always the gentleman I did as she asked. I must have done it right as she not only moaned but complimented me on my technique. She then got me to get on hands and knees while she oiled up her cock. She then pegged me bare back. It was amazing, much better than my previous experience with the strapon. Just before she came she pulled out and jerked off spraying cum on my back.

I thought it was a great experience but it turned out she wasn’t finished. I was on my back and she masturbated me until I unloaded. By this time she was hard again. I was so surprised how quickly she got hard again. She told me to roll over, this time lying flat. She put on a condom this time and again greased up and pegged me. It took longer for her to cum this time and I didn’t mind a bit. She started to really pound me and I realised she was not just doing it for the money but she was enjoying it. She came and told me she didn’t want to stop. Her cock finally went limp and she pulled out. She showered but the bathroom looked less than hygienic so I passed. I paid her B1,500 and we went our separate ways. I did try to find her again but she had apparently left the bar.

Having experienced anal sex with a Ladyboy I was eager for more. With “A” missing I checked a couple of sites on the internet and found one. Looking through I discovered a woman (and yes, I see them as women) named “P”. A little more expensive but no bar fine or drinks bill. I contacted her and arranged for her to visit at my hotel. Much better. She arrived right on time and knocked. I opened the door and was surprised. Her profile had said she was tall. Turned out she was 180cm (I am 183). Slim and very attractive. I invited her in and we had a coke. She said she wanted to have a shower. I had already had mine earlier.

“P” came back wearing just a towel. I had already stripped off and was also just wearing a towel. We finished drinks and she got amorous. Suddenly she stood up, knelt on the couch we were sitting on, dropped the towel and demanded I suck her cock. Her profile had said “equipment large”. It didn’t lie as 7+” waved in my face. Again, always the gentleman, I sucked her rod. She moaned and urged me on. Finally she stepped back, grabbed my hand and led me towards the bed. Just as we got there she knelt down and started to suck me. I was tempted to grab her head and push deeper but one doesn’t touch another person’s head in Thailand. So I rested my hands on her shoulders. I didn’t need to grab her head as she was an expert and got me close. She stopped and said “bed”.

I had put a towel on the bed and she had me put a pillow under it. With my bum on the pillow and my legs in the air I gave her maximum access. She put on a condom then some KY and pegged me. We looked in each’s eyes both obviously enjoying it. Yes, she was a professional, but I have learned that they love sex if treated with respect. “P” got more excited and by the time she came she was pounding me like a machine. She had grabbed my legs for leverage and I was masturbating. It would have been a toss-up who was moaning the loudest. Finally she came and I did a second or so after. We lay on the bed puffing and panting. It was so good. I paid B2,500 and she gave me her phone number before she left and said she wanted to see me again, soon. I knew I wanted her again.

Several days later I rang her. I remembered her profile lasted several other Ladyboys she did threesomes with. I asked about that. She said one friend was available the next night. Funnily enough this friend, I will call her “M”, had a western name which was the same as my ex-wife. I thought that would be funny so I told “P” to bring her. But that is for Chapter 2.

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