We first made contact about three years ago, on one of those dirty dating sites. I was showing my tranny profile, Velvet, at the time, and was being hit on by a bunch of dirty old men, when this “Mariah” person said, “Hi.” I was in a pretty sarcastic mood at the time, and was slightly peed off, as the guys I had been chatting to were only interested in one thing, getting their rocks-off.
Anyway, Mariah said she liked what she saw, just loved sexy trannies, enjoyed reading my profile, and decided to contact me. I was very skeptical to begin with, as her profile was almost non-existent and she didn’t show any photos at all, so I put two and two together, and guessed she was some tattoo chubster from some god-forsaken place, probably a size 30, with an IQ level similar to that of a banana! (I know, very rude of me!)
She even suggested she could e-mail me a photo, to see if I was interested. If I liked what I saw, terrific, if not, no harm done! Not my thing at all really. It would mean me giving her my e-mail address, and I’m very conscious about my privacy and security. Some terrifying thoughts of a stalking tranny-chaser entered my mind. I’m not sure what it was though, but she was really polite and kind, by showing a real interest in me and asking some fabulous questions, and as she seemed genuinely interested, I took a risk and gave her my e-mail address.
Well, fuck me, what a surprise! She was awesome! A “yummy mummy”—a MILF. I was lost for words, shocked even and very, very pleased! (Marks out of two? I’ll give her “one”!) She was about the same height as me, perhaps nine or ten years younger. She had dark, shoulder-length hair, was slim-ish (I would say about a size 14-16) and had a pronounced cleavage, curvy hips, fabulous legs, and a smile to die for. Perfect!
We chatted for hours, got to know one another and exchanged loads of photos, all of mine in transvestite mode of course. As days went by, we learned more and more about each other, about our pasts, what we had done, what we liked, disliked, and eventually, what turned us on. We just seemed to click with each other straight away. Nothing was taboo, nothing was hidden. Oral, anal, peeing—anything was asked, and yes everything was told. She was really turned on when I mentioned my bi-curious side, and loved the notion that I adored tranny cock, just as I was equally turned on when she mentioned she had taken more than one girl to bed with her. Mmm, I just adore lezzie sex; don’t you?
Things got even better during the second week when, during one very horny early morning chat, she asked me to masturbate for her. Oh fuck, I just loved doing that, especially when she talked dirty to me, and she loved it when I spunked. She had gotten pretty turned on too, and told me she had done a two-fingered quick-step on her clit as well. Fabby!
Soon, though, she asked about arranging a “meet”. We had gotten to know one another on a very intimate level, and she felt pretty comfortable with the idea of hooking up and having a night out, and perhaps booking a hotel room. I was okay with the “meet” thing, but a little concerned about the hotel idea as I was extremely worried with the prospect of her seeing me as a man. She had only ever seen me as Velvet, and I thought she would probably run a mile after she had seen the photo of me in “man-mode”, and never contact me again.
I am not unattractive, but I am quite shy, and a little introverted, and I always appear to be at least ten years younger when dressed as Velvet. I feel much more confident and outgoing with my Velvet side, and wasn’t keen at all on showing her me! She told me not to be so silly, and send her a man-photo. I took a deep breath, said what the fuck, and pressed “send”.
Heavens to Betsy, I damn near shat myself when I received her answer back. It was, “Phwoar!”
Things, believe it or not, got even hornier between us over the next few days (go figure!) Texts were now pervertedly dirty, and very explicit and some very raunchy and sexy photos were exchanged. Perversion was always at the top of the list, and I gave up counting the amount of times I wanked for her. I asked her where she would like to go when we met up, and she suggested either a BDSM club, or a well known Tranny club, both located in the Minories area near Tower Bridge. I thought the BDSM idea would be fun, and Mariah suggested we make a full night of it and book a hotel room somewhere. We could have a fabulous night out, enjoy some weird and wonderful entertainment, and if we’re both really horny when we get back to the hotel, we could participate in a bit of “Off piste fucking”, by me skiing down the old pink run! Oh, my god, give me a season’s pass… now!
Mariah arranged for us to meet in a hotel near Tower Bridge, and told me to text her when I arrived.
The journey there was thrilling, as I was dressed en-femme as we say. It was so much fun driving through London on a warm summer’s day. I was wearing black pedal pushers, three inch heels, a corset, a black tank top, a pink, calf-length chiffon cardigan, dark hair, loads of cheap jewellery and, of course, full make-up. I thought I looked okay. Maybe passable, but you’re never too sure, are you? Most of my friends say I look pretty convincing, and could maybe pass off as a woman… at a distance of a hundred meters or so!
I arrived at the hotel early evening, and walked past the doorman. He didn’t even give me a second look. Phew! I texted Mariah, and made my way to her room. She had left the door slightly ajar, and when I entered, I was greeted by the most delicious sight I had ever seen.
There she was, naked, except for a pair of black stilettos and a pink feather boa around her neck. She was lying back on a wide double bed, sucking one finger and massaging her clit with another! She asked me if I liked her look. I think I just dribbled!
She said I looked gorgeous and as sexy as fuck, and told me to drop my things, get my cock out, pour myself a glass of Pinot, and come over to the bed and eat out her pussy.
My girl cock was now so erect and hard, it had started to throb. Mariah leant over, gently inserted a strawberry into her cunny, looked at me with the dirtiest look on her face, and asked me if I fancied eating it! Do fish fuck in water?
My tongue was between her thighs quicker than you can say, “Usain’s bolt.” As I spread her thighs further apart, I lowered my tongue onto her gorgeous, sopping wet, shaven pussy, and just licked and sucked her cunt from clit to arsehole. A strawberry had never tasted better. I licked her fingers whilst she masturbated, and she loved how I could make her cum with my fingers and thumb as well. I sucked on finger after finger, even after she had inserted one or two into her bum hole. Oh my, I just loved her taste. Both holes. So yummy.
I made her cum again and again. She loved it and she screamed (probably more for my benefit than for the people next door!). She drove me crazy mad, and really turned me on with her moans, her cries of joy and screams of pleasure, and her ability to use such profane language. Her ex-husband never liked giving her oral pleasure. I was making up for it big time, and her juices just flowed and flowed.
One thing though—I know it’s crude, and so do forgive me for bragging a little—but the main reason why I’m called Velvet, it’s ’cause I know how to use my tongue! (I had a really good teacher!)
After what seemed like hours of oral pleasure (okay, okay; probably about thirty minutes) she pulled me up to her, slid her tongue into my mouth, gave me the wettest no-holds-barred, deepest tonsil-hockey kiss ever (damn, that girl can kiss!). Then she looked deep into my eyes and, in a very sultry sexy voice, told me to grab my cock, and wank over her titties for her (just think of a Southern Yankee voice, and say, “Oooooh… don’cha just loveeee doing that!”).
My cock is shaved smooth, cut, and fairly big. Not massive, but a good size, and I tend to be a shooter, not a dribbler. I am thankfully, a heavy cummer too, so loads of jizz to play with.
As I knelt between her thighs, she continued to play with her clit. I started to stroke my now aching cock. She teased me with her feather boa, and her fingers brushed against my mushroom shaped cock head. Every now and then, she would lean forward and suck my girl cock to give it plenty of lube, and then wrap her fingers around my shaft and wank it also. She could see how much I enjoyed it—see that I was going to burst any second. She told me to enjoy it, ’cause from now on, she told me, I would only be allowed to wank with her permission. She knew I was a dirty little wanker, and loved wanking when ever I could. Now she would control me. She was gonna make me her wank slut.
She asked me if I let guys wank me, when I was dressed as a girl, if I let other TV’s wank me, if I let anyone wank me. “Yes, yes, yes,” is all I could say!
“Mmm,” she replied, “We’ll see!” I noticed the little smile on her face.
As she teased and goaded me, I could feel the heat increasing in my swollen balls. I longed for release, ached for relief, begged her to let me cum. I was wanking like a mad tranny, my hand moving at a thousand miles an hour, building to a huge climax. I had reached the point of ecstasy, my mind blown, my hand just a blur. I was about to explode and all of a sudden, I did.
My cock erupted. A huge dollop of spunk splashed onto her tits, followed by another, then another and another.
“Yes!” she said, “You dirty little wank slut… more!”
Oh, god! She made me spunk n’ spunk. She eased a lubed finger into my arse, and she finger fucked me as she squeezed my cock to force out every last drop of cum.
When my cock had finished twitching and spunking, she pulled my head down to her tits, and rubbed my mouth and lips against her so I could suck up every drop. She took one big glob of jizz, and used it as lube on her cunny, as she fingered herself again for me.
After I had licked her clean, she leant back, reached into her overnight bag and pulled out a strap-on and laid it on the bed. She told me that it was for later, when we returned after our night out.
Mariah asked me if I wanted her to use it on me. I said I didn’t know. I wasn’t sure what to say. She asked if I wanted to be fucked in my arse with it. I said nothing. Too afraid to say. Too ashamed to say yes!
She grabbed me round the neck and pulled me to her, her face an inch from mine, and said that I would learn to love it, learn to beg for it and would succumb to her every request, her every need. I would be her wank slut, and she my wank Mistress. If I resisted, I would be punished, but if I complied, the rewards would be mind blowing. She looked into my eyes, and asked me if I wanted this.
I couldn’t believe it. It was what I wanted. I fell to my knees, kissed her feet, and I was now hers.
She told me that when we left the BDSM club, she would take me to an after-hours club, just off Commercial Road. It’s frequented by trannies, transsexuals, gays, tranny-chasers, and one or two bi-girls, amongst others. There, she would introduce me to a few of her friends. Have me play with one or two “cute boys” she knows, and let some yummy, little, cross-dressing slut suck on my cock, and let me spunk into her mouth. It’s a den of iniquity, she told me, and she knew I would love it. I couldn’t wait to get there!