![1451067954049[1].jpg](https://i.imgur.com/5Uz44lN.jpg "1451067954049[1].jpg")
I lost my TS/Shemale/Futa virginity yesterday evening - I've always had a femdom fetish and that coupled wit years on 5chins turned me onto a chick with a dick fetish. I've been working myself up to it for about 3 years and decided "fuck it, just do it". Met pic related in London for about 1.5 hours yesterday, cost 200GBP.
>emailed Isabella a couple of days before and arrived the date of Christmas eve as this was her last day working for a while
>had a couple of vodka and oranges as I was nervous, came a bit early and phoned her to say I was there, she said no problem and to just come up
>she opened the door to her place and holy shit she was really hot - very feminine, very voluptuous, and 100% passed
>I had been worried before that she wouldn't be totally passable and I'd have to say "sorry, I'm not into this", but she just looked like a very attractive woman
>she kissed me on the lips and told me to come in
>bit of small talk and I gave her the envelope with her money in it
>she told me to sit on the sofa in the living room and went into the kitchen to get us both drinks (and count the money, I assume)
>she comes back with two glasses of red wine and sits next to me, close enough that her leg is touching mine
>I'm getting stiff already
>we chit-chat a bit and she's touching the inside of my leg
>she tells me she's mostly a top and doesn't usually bottom in her personal life, but is happy to do so for me "if it goes that way"
>she gets close and starts deep-kissing me
>I'm diamond hard now
>we break off kissing, she smiles, takes me hand and move it to the inside of her dress guiding my hand to her cock
>her cock is literally 2 thirds of the way down her thigh, rock hard, and insanely thick - its shape is poking through her dress
>I just said "oh wow"
>her ad said she was 24cm, which is 9.5" - I had assumed she was greatly exaggerating but nope
>she hikes her dress up and her monster cock is exposed, already glistening with precum at the tip
>she gives me another kiss on the lips and says "on your knees", I do as she says and she puts her hand behind my head and guides it to her cock
>I suck her off for about 10 minutes
>she tells me to stop as she doesn't want to cum yet
>she leads me to the bed room and playfully pushes me onto the bed
>she sits on my stomach straddling me and puts her tits in my face, smothering me for a few seconds then put her nipple in my mouth and tells to suck it gently
>I do this for a while and she changes breast, she seems to like it a lot
>I can feel her cock on my stomach and chest, I can feel her pulse through her cock
>she tells me that she is going to fuck me hard and I just nod
>I was quite nervous about it as I've never really practised and didn't expect her to be as big as she is
>she puts a condom on and takes lube off the bedside cabinet and lubes both her cock and puts a lubed finger in my butt crack
>"So you're really an anal virgin then . . . you know this is going to hurt a lot?" I just nod. She grins and says, "I really mean it. And once I start fucking your ass I'm not going to stop, even if you cry about it" This turned me on a lot
>She told me to turn onto my stomach
>she straddled me just on the mid-upper thighs
>she put the head of her cock on my hole and swirled the head around, pushing into me, it took her about five minutes to get the head past the sphincter
>she told me "this is going to hurt, but you're doing it for me, ok?"
>she pushed my cheeks apart and lowered her hips into it, not fast but with a constant force
>I was shaking a bit as it hurt like a motherfucker - still hurts, actually
>she laid on top of me and I could feel her tits squishing up on my back, she kissed me on the neck and after about a minute started to slowly withdraw and then go back in, she did this for about five minutes and spoke to me reassuringly
>I could feel her cock push hard against my prostate - it felt like she was up against my belly button
>>25245229
OP is a faggot baka desu
>she asked "Just gentle or harder?" I said "whatever you prefer"
>she speeds up gradually until she is fucking me like a pornstar - this was hot but 90% pain and 10% pleasure
>I ask to switch position so she tells me to lay on my side, she gets behind me, puts the head of her cock against me and pushes in while pulling my hips towards her
>I gasp as it was not nearly as gentle as before
>she kisses my shoulder and bites it a little, starts pumping hard again
>she reaches around and starts jerking me off
>I don't really want to cum yet as I wanted to fuck her too, but she gave an amazing handjob + the pressure on my prostate meant I came in about two minutes
>I shot my load in three spurts - I don't think I've ever came so hard
>she slows down a lot and whispers that she's just edging but that I'm "not done yet"
>she pulls out, tells me to get on my back
>she takes off the condom, straddles my chest and puts about 3 inches of her cock in my mouth, I fondle her tits while sucking her
>after a couple of minutes she takes my head in her hands and begins to pump her hips
>I gag a little as her head is entering my throat in and out
>she withdraws a little and shoots a really big load over my tongue, she says "be good boy and swallow it", and I do and she giggles a little
>she hugs up next to me and snuggles for a while
>>25245256
Thanks, senpai. Love you too.
Son, you paid someone to fuck you
When that sinks in, it's gonna fuck you up.
>>25245439
I'm not even bothered, m8E.
>24cm
no fucking way
What're you fuckin' gay?
>>25245278
Sounds nice. If you do it again get her to ride you maybe, or try anal orgasm.
> tfw straight but erect.
Intriguing stuff, man.
>>25245229
My dude, kill yourself
>>25245594
Link her profile pls
>>25245550
>24cm
>no fucking way
That was my reaction to her ad - assumed she'd be about 7" maybe 8" at the most. My dick is about 6.25" when totally hard - hers was at least 150% of my length and probably nearly double my girth.
>>25245691
http://profiles.birchplace.com/bigcock24cm
sounds hot OP. did she really charged only 200 gbp for all that? she was the one enjoying it the most I guess but still RLD whores are able to charge you extra for changing positions not speaking about kisses and other stuff.
>>25245928
>did she really charged only 200 gbp for all that?
Yup. She's an escort, not a brothel/RLD girl - you pay a flat rate for her time and can do whatever is on her "likes list". I paid 200 GBP (pounds, not good boy points) for an hour but stayed about 90 minutes from stepping into her apartment to stepping out.
Why didn't you buttplug beforehand
>>25246011
well lucky you, just reading that stuff made me rock hard. too bad I live so far away from UK. maybe one day... btw any word on STDs? that is pretty much the only thing bugging me about this kind of leisure activities.
>>25246057
>Why didn't you buttplug beforehand
It didn't cross my mind, to be honest.
>>25246129
>btw any word on STDs?
Wear a condom? She told me she's Greek/Spanish, so not Latin American where I guess STDs are more common.
Very believable 8/8 OP. If you took 24 cm without preparing, there would be smeared shit all over her sheets right now.
>>25245229
You should have practised first with a buttplug to get you loosened up a bit.
Also there's no such thing as chicks with dicks, only guys with tits.
>>25246224
>Very believable 8/8 OP. If you took 24 cm without preparing, there would be smeared shit all over her sheets right now.
I had a soap/warm water enema beforehand, I've just never had more than a finger up my butt before her.
>>25246202
>Wear a condom? She told me she's Greek/Spanish, so not Latin American where I guess STDs are more common.
She also said she only tops in her personal life, so that makes getting anything less likely. And I believe her based on her performance.
>>25246202
yes but still kissing or sucking dick can give you some nasty surprise like herpes or chlamydia. but maybe I am just way to anxious about this stuff.
>>25246236
>You should have practised first with a buttplug to get you loosened up a bit.
In retrospect, i agree.
>>25246254
>soap
>enema
Nice b8 m8.
>>25246316
>yes but still kissing or sucking dick can give you some nasty surprise like herpes or chlamydia. but maybe I am just way to anxious about this stuff.
And crossing the street ca get you hit by a bus. You're probably more likely to get an STD from eating/going down on some roastie from a bar - a pro escort giving people STDs would be getting terrible reviews online and would essentially be out of clients.
>>25246348
>Nice b8 m8
Huh? Bought a disposable enema, filled with warm water and a bit of hand soap. What's the issue?
>likes to top
>becomes trans
what is the point man?
>>25246361
>You're probably more likely to get an STD from eating/going down on some roastie from a bar
I see your point.
>>25246395
>what is the point man?
People are strange and complex creatures . . . no fucking clue, haha.
>All of this for 200 bucks
Goddamn what a steal. I really hope you're not lying OP, sounds like you had the night of a lifetime.
>>25246709
>All of this for 200 bucks
That's British Pounds - about $300 USD.
>>25245439
>Son, you paid someone to fuck you
I'd be more ashamed of being a tripfag on /r9k/ tbqh senpai, you fucking faggot.
>>25245229
Hot as fuck OP. Any more pics or link to her escort page?
>>25245255
>>25245278
> I've never really practised
> this was hot but 90% pain and 10% pleasure
if theres any pain at all, you're doing it wrong. absolute idiot for getting assfucked with no prior practice
>>25246316
> maybe I am just way to anxious about this stuff
you're not, thats basic precaution. this is a literal whore we're talking about
>>25246394
shouldn't put anything in ass you wouldn't in mouth. why the fuck would you put soap up there, you really are an idiot
if you don't learn basic shit like in this post you're gonna fuck ur shit up at some point in your life. its not about 1 event, its about a lifetime of poor choices that catch up to you. have fun with your future broken ass/std's..etc
>tfw it was only a one-night whore thing
>tfw no shemale gf that does this every day as well as having a relationship with
;____;
>>25247082
I agree that soap in the ass is bad idea. even water from tube is not the best idea since it contains some basic disinfection which may kill the good bacteria that process your shit.
>>25247082
as a guy whos gf is trans who fucks him i'll say this.
Anal Sex does hurt if you do not do it reguarly. If you do it reguarly its fine but if not, it can and will hurt a lot.
>>25247127
>tfw actually have a shemale gf
never been happier lads
>>25245278
after you came did you regret it and lose your attraction to her? when i cum i instantly regret fapping to shemales
>>25247249
no gf at all but I play with my ass from time to time and it only hurts if I have hemorrhoids. but it is true that I never tried dildo as huge as OPs trans.
>>25247373
I know that feel. the moment of clarity that reveals all her manly features.
