First time sex experience with a real shemale escort

My first experience with a real shemale escort, was everything I had dreamed it to be and more.  It took so much planning on my part, I wanted the shemale escort experience to be something I wouldn’t regret , and obviously I already had some apprehensions about it.

Real shemale sexy webcam chat

When I found the T girl I was looking for, after looking all through various escort sites , I was very excited. At first I had to mail a few, I needed to make sure the one I ended up with was interactive and communicating on my level. Strangely I actually also wanted one who had English as a primary language , her mother tongue if possible . Which is kind of novel for me as I’ve always been quite turned on for many of the T girls from Thailand, many of whom do not speak perfect English , but usually if it’s good enough for them to convey to me they’re having a good time, and to direct me and take my directions, then I’m good to go . I’ve had a lot of hot webcam experiences with Shemales from Thailand, and other countries. A couple of really sexy T-girls from Brazil. Both had perfect English to be honest , but this time, I wanted a local accent. At least a British one. I think maybe because it was my first time with a transgender lady . Actually my first time paying for sex in real life at all, that I felt it could make me feel more comfortable, hearing an accent I was over familiar with , and I believe it was a good call . In hindsight for the first T girl sex, it was a good call, but for future, I think now I’m well and truly broken in ahaha, and I don’t need anymore cushioning, I would be more than happy to go for some of those sexy trans ladies from abroad . The Shemale I chose was on a webcam site , which made it hotter, as we had some pretty horny webcam sex before we arranged to meet live. I think for now I will keep this a criteria , and stick to escorts who I know work on webcam , as it does make it so much sexier, being able to have some build up , through text chat, then webcam chat , and then finalising in meeting and fucking . Something about that makes the whole experience so much sexier, and so much more organic feeling. We had really got to know each other over the course of a few days before we ended up in the same room with her . This helped, because although I was quite cocky on cam , excuse the pun , when it came to meeting her, I was pretty nervous, which isn’t like me , I’m a multi million pound international business manager, so feeling embarrassed or nervous, is usually when I’m out of my depth ,and it’s quite a unique one for me, luckily she was already aware of my concerns, and did everything she could to stomp them out , which worked.

Live shemales webcam sex

When I turned up at her hotel , ( you will find most t girl escorts, well maybe not just the shemales, maybe most escorts, but having never been with any others, I can’t comment , will not meet you in your own house , some will offer at a push to come to your hotel room , but I was nervous about that , as I didn’t want to get thrown out of a hotel booked in my name, I stayed quite locally , and like I say , I’m a well respected member in my community , many , if not most , will prefer that you go to their house/apartment, again an option I wasn’t keen on , I just didn’t feel entirely safe , meeting somewhere that gave them so much an of an upper hand, and then there’s the last option , which is to go to their hotel room , a few offer this, less than those who will let you go to their flat , but more than those who would come to your house, in hindsight, probably preferable, as I don’t know how keen I am on a stranger , meeting through this world , having my home address , although I’m sure there would be nothing wrong with it , it’s better to be safe than sorry , I suppose) And so I went to her hotel room . She assured me it would be a hotel with little to no reception activity , so I would not be questioned on my way in . I expected a low rate hotel , and expected something dingy . I don’t know why , maybe I’ve watched too many movies, maybe I’ve watched the wrong type of movies, anyway , it definitely wasn’t either, it was a beautiful hotel , and she was right, when I got there, there was no one manning reception,there was a bell you could ring for attention, but as attention was the last thing I needed, I walked straight on by , and up to the room number I had been provided with . She opened the door right away . She looked even better in person than she did on the photos, something else I was not expecting. I think he feminine aura, and her personality and warmth , framed her physical beauty , and in reality just seemed so much more alluring. She also smelled divine . She ushered me in, to a room she had obviously added some feminine touches to . There were roses on the side. Some bottles of her perfume and make up on the dresser. Some of her underwear lay on the chair by the bed, and a few outfit changes hung close by . She herself was dressed in a short black dress, high stockings , which the tops of could be seen , if she bent over- of which she did, a lot . High black heels , and a pair of beautiful diamond ear rings, her black hair hung loosely and free over he shoulders. She looked like a very classy high end business woman , off on a work night out . I was really surprised. I was expecting her to answer the door in something more promiscuous . Don’t get me wrong, it was sexy as fuck , but given the context of our meeting, I was thinking more PVC dress and plexi glass stripper shoes, I was very delighted with what I actually got . Having never met a shemale in real life, and only on webcam , it’s hard for me to compare, but she was a 10/10 . She laughed gently at me, and told me not to be nervous . Asked me if I’d like a drink . As she bent down to the mini bar, that black dress slid up her thighs, and I glimpsed her stocking tops, and almost her panties . She grabbed a bottle of beer , and asked me if I’d like a glass . Normally I’d have declined, but this shemale seemed so classy , I felt like in the presence of a lady , I should take a glass, so I did . She didn’t take the same approach , and cracked open a beer, which she preceded to drink from the bottle . It amused me a little and lightened me up , not the fact she was drinking from the bottle, just about everyone I know would do that , including myself, but my own preconceived and over thinking notion, that I should not in front of her . It also loosened me up , and I realised there was nothing to be nervous about . Well not regarding the fact she was a shemale anyway . But maybe about her long sexy shemale legs , her feminine body , her long eyes lashes and feminine face, She was a beauty – and the sex was just as amazing. First time sex with a shemale from a webcam meeting.

Sexy big dick shemale for webcam sex

Pretty shemale for webcam sex

Gorgeous webcam shemale for sex chat

So all in all, what do I think , amazing .  Would I do it again ?   You bet I would .  I’m already researching who I would like to next spend some time with .   I would go back to the same girl, but she’s away on holiday , and I’m not sure I can wait , although I’m sure I will be back to see her again , probably as soon as she is back .  Nothing stopping me from checking out who else is on offer before then though , as there’re quite a few I’ve been chatting to on these webcam sites, and quite a few on escort sites who are keen to meet me .   Usually when you become a member , you get to see more dick pics, or any dick pics for that matter. A lot of the girls keep their dick pics hidden , until you join as a member, so it’s worth doing, at least for me . Not that everything is about the dick , of course  , especially with trans women , it’s about so much more, but it is nice to see a big dick prior to booking , well if that’s what you’re looking for, but who of us doesn’t love a sexy chick with a big dick haha 😀   Until next time.