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Old 02-18-2008
capablanca capablanca is offline
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Default Recent wonderful experience with a shemale - my first taste of cum

In my first post here I described my first encounter with a shemale - an amazing experience. One thing I've been looking for since that first experience is a shemale who would cum in my mouth. Now one might think that this wouldn't be too hard to find, but in fact it is a bit difficult. First of all, the only shemales I've been with have all been escorts (I've seen five different ones so far, all in Toronto). I'll mention by the way that I really wish I'd gotten into escorts when I was younger -I'm well over 40 now, and I don't think I could get a shemale for free to save my life. Sad, but true. Anyways, escorts don't like to orgasm with a customer until their last of the night - they have to keep themselves a state of arousal through the evening. And I'm not a late-night person. So when you add all this together, I was having no luck at all in my ambition - until this Saturday.

I was allegedly at the office working - in fact, I did come in and do some work. But I foolishly logged on to the web, and surfed through the Red Zone, Eros and so on, looking at various shemales. The urge hit me, and in no time I was on my cell phone, looking to see who was available. I made an appoint with A___ (I won't give her name here). And off I went to downtown Toronto for some fun.

A___ was a bit different from other shemales I'd been with. All the others had implants, and quite nice ones. A___ had none, and whatever hormonal therapy she had had not created much in the breast department. But she was very petite, very feminine. Barely over five feet, and she could not have weighed more than 100 pounds - was probably more like 90. She was also something that I don't encounter with escorts all that often, whether shemale or female - she was really into kissing, and was a wonderful kisser. So we made out on her couch for the longest time, and after a while, she undid my pants, and pulled them down along with my underwear, freeing my raging hardon. I'm exactly 6 inches, but she fussed over it like I was long John Silver or something. She had no problem at all taking me right to the root, and she kept me on the edge forever without letting me cum. I loved the way she maintained eye contact while she slowly moved her head up and down.

After a blow job (not to completion) that went on forever, she got up and undressed. Her cock was about 5 inches. This is a good thing for me, because I have trouble handling anything larger with my mouth - just can't get it all in.

Now one interesting thing about the session was the change in her personality as things progressed. I wouldn't describe her as passive at the start - not at all. But certainly I was the one in charge, at least at first. But as things went on, a role reversal gradually took place. It started when she told me to suck her cock - didn't ask, or invite. She just told me to stand up, and then she sat on her couch, spread her legs, and said, "Suck me - i'ts my turn." Her tone was still feminine and sweet, but a bit peremptory. I liked that a lot, and I started to work on her right away, kneeling between her legs and taking all of her semi-hard dick into my mouth. I wasn't nearly as good as she was at giving oral, but I must have been ok, because she got hard really quick, and I was really relieved that I was able to handle her. She started to instruct me on what to do, telling me to use this or that technique - licking around the head of her cock like a lollipop, using my hand to pump up and down while I suck her, spitting on her cock for more lubrication, and so on.

After a while it was pretty clear that she was in charge. Then she took my head in her hands, and asked me what kind of fantasies I had. I was really comfortable with her, so I told her right away. I explained that I've always wanted someone to cum in my mouth and on my face, and to be made to eat it all up. I added that I'd like it even more if while I was doing this, she was to make a video using my cell phone.

A___ was pretty cool about this. She had no customer booked after me, and said she could do it, but would charge extra, because she'd be out of commission for a little while afterwards. I agreed with no hesitation at all. It was great that she was agreeable to the camera thing, too.

"But I'm afraid you might try to back out of this," she said to me. "Some guys think they want to swallow my cum, they chicken out when I start to orgasm, and it's a real turn off for me when I'm expecting to cum in a guy's mouth and he changes his mind."

I promised her that I wouldn't change my mind - I was really eager to give this a go.

"Let's just make sure, shall we? I'll be right back." She stepped out of the room for a minute to her bedroom, and came back with a goddamn pair of cuffs. She told me to get onto the couch in a kneeling position, and after she did so, I didn't say a word when she cuffed my leg to one of the iron handles of the futon couch in the living room. Looking back now, I have two thoughts about this. It was incredibly stupid of me, but on the other hand, just thinking about it makes me rock-hard.

Without asking me, A____ got my cell phone out of my jacket pocket, and in no time figured out how to get the video going. She started filming me, while at the same time gently stroking my cock with her other hand. She started asking me questions like it was some kind of interview or something. She asked me my name, which really scared me - what if she released the video? When she saw my hesitation, she squeezed my balls slightly - not enough to hurt, but enough to make sure I knew that it could be painful if she wanted it to.

"Your wallet's in your jacket, too, so if I want your name I'll just go get it. But I'll give you another chance to tell me."

And so I gave her my name, my goddamn address and answered any other questions she asked. Up to this point the phone camera had been pointed only at my face. But then she pointed it down at my swelling hard-on, which she had been stroking continuously as she asked me questions.

"You're pretty excited, I see. Now what are you here for today?"

"I'm here to give you a blow job," I replied.

"Anything else?"

"And to swallow your cum," I added.

And we got started. She lay on the couch, her body inclined upwards somewhat, her head on a pillow. She was quite comfortable and able to video me as I stretched out and started to work on her. In no time she was really hard again, and soon I was in the rhythm, my head going up and down on her cock. She was giving me instruction again just like before, but this time it was all on tape, with me obediently following every instruction. Every now and again when a bit of precum leaked out of her, she pulled out of me, and got me to lap up the fluid, making sure she got a good shot of it each time.

After a while she was starting to lose control, her hips bucking as I continued to suck and lick her. Finally she stood up on the couch, and had me raised myself to my knees before her. She started down at me, the camera still going. She took hold of my hair, and shoved her cock back in my mouth, fucking me while pushing my head forward in time to her thrusts.

"Oh fuck fuck I'm cumming I'm cumming!" Aside from moaning about the load she was about to make me swallow, she was using my name too, first and last name, so that there was no doubt at all to anyone watching the video about who I was. No deniability for me whatsoever if the video got into the wrong hands. Or, god forbid, was posted onto the web. And so when she suddenly pulled my head back, and said "SWALLOW! ALL of it!", I knew I had no choice.

The first jet of cum went straight into my waiting mouth, which I'd kept wide open at her order. The second followed the first. I barely had time to notice the taste before she shot two more loads onto my face - this was something I hadn't been expecting - I'd imagined that it would go straight into my mouth. One blast hit me in the eye and I jerked my head back from surprise, but she grabbed my head, and forced me forward again. She gave a few more smaller blasts, these spurting forward onto my nose and lips, some of it falling back onto her still-hard cock. She let go of me for a minute while she lay back again, and then told me to lick up every drop of her cum from her body. And I did. All of it. I licked her cock and balls clean. As I did so, she collected each of the remnants of her spurts off of my face with her fingers, and put her fingers in my mouth for me to suck clean. She kept her cock in my mouth, and I continued to suck and swallow the small leakage of cum than came from her as her cock gradually shrunk.

It took quite a while, but eventually I'd satisfied her. To my great relief, she gave me my cell phone back. I don't know what I would have done if she'd copied it to her computer first. She uncuffed me, and then treated me to a fabulous blow job, inserting her finger up my ass to massage my prostate as I came violently in her mouth. She let my cum dribble out of her onto my cock, and then lapped it back up. She did this several times before finally swallowing.

It's been two days now since this experience, and I just can't stop thinking about it. I put the video on my computer, and no, don't bother asking me to post it. I'm probably going to erase it, because I'd hate to have my computer stolen or something and then find out that the video's all over the web.

So that was my first experience swallowing cum. Scary at times, but no harm done, and lots of fun. Tasty, too. Can't wait till next time.
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Old 02-18-2008
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tlover tlover is offline
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Ooooh that was scary and very horny all at the same time, thanks for taking the time to wight and tell us all about it.
ive had similar fantasies of swallowing ladyboy cum for a long time now and i saw myself in that story, it was very scary i could easy imagine something like that happening to me, getting carried away in the excitement and doing something very silly, with a lovely tgirl.
Yes very scary but very horny and you told it so well i felt i was there experiencing it great stuff.
thanks again cap.
Tlover Give it a go, you never know.
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Old 02-18-2008
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TSLuva TSLuva is offline
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Yes like tlover says I don't think will be many reading that & not imagining themselves there instead of you capablanca
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Old 02-18-2008
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ila ila is offline
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Great story. Made me wish I was there, except for the handcuffs and video part. A sounds absolutely delightful and sensuous.
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Old 02-18-2008
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SSL SSL is offline
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that's surely a great and very horny story capablanca. As for the video, let me suggest you to edit it and crop out the parts with your face in and mute the sound where she calls out your name. In other words, erase all evidence that it was you and then remove the original file. Something tell me you will not regret it
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Old 02-20-2008
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stephen54 stephen54 is offline
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Fabulous and very erotic, braver guy than me though, but the risk paid off, made me rise reading it.
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Old 08-08-2009
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bobbo_11 bobbo_11 is offline
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great experience
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Old 08-08-2009
dami dami is online now
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I almost came reading this. Great story
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Old 08-08-2009
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MxKanAmrKan MxKanAmrKan is offline
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great story thanks for sharing.
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Old 08-21-2009
tamutamu tamutamu is offline
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Iswear Im gonna have atranny cum in my mouth sometime!!! Imma lube this hard on of mine for now!!!
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Old 11-26-2009
funboyto67 funboyto67 is offline
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Hey. Toronto guy here.. would love to play with her too.. are to point me towards her site or number? she sounds hot!!!!
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Old 02-19-2010
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bernybudmon bernybudmon is offline
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Default hi

dam good experience got me rock hard and pulsing want to releases my load
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Old 02-21-2010
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Demonic shemale licker Demonic shemale licker is offline
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What a fabulous story, i would love cum in my mouth and face!
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Old 02-23-2010
Alanz Alanz is offline
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Simply awesome account. My first encounter with the beautiful Gizel, resulted in her riding my cock whilst she shot her load up my chest! I"m seeing her on Monday and I know what to ask for now. thanks Capablanca!!!! I can"t wait for my first taste of Shemale cum. Ecstacy here I cum!
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Old 02-25-2010
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What a story man I have say I have wanted to try something like that but just not the video part.
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Old 02-26-2010
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merelypink merelypink is offline
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great story thanks for posting!!
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Old 04-28-2011
boby6 boby6 is offline
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that was a hot story. could u link me her page im in Toronto too
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Old 05-11-2011
ssell10 ssell10 is offline
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Default Tonite!

Im off to meet a trans escort in glasgow very soon. Shes a sexy dom and has been sendin me txt messages that have left me hard all day. She says she wants me to taste her cum, should i swallow? What are the risks?
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Old 09-02-2013
john90640 john90640 is offline
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Default My fantasy too!

This is very much like my fantasy. I want to marry a (shemale) T-girl that has the same desires. I also want to transition and become like her. I want to become a TS leather wearing life style dominatrix switch. Where is the blow job emoticon?
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Old 09-04-2013
ydffggh ydffggh is offline
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Great story. I love the taste of pre cum but have never gone the whole way
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Old 12-02-2013
LovinThaTSLadiez LovinThaTSLadiez is offline
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Great story!
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Old 12-02-2013
horny4sex horny4sex is offline
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That was a great story I was so horny reading it I cumed 4 times. Im still hard and horny I think im going to read it again amd jerk off and eat my cum again. I love this story.
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