Fantasy

Well, firstly I have very few taboos with women, mistresses or subs. So there’s not much I won’t do to please or take pleasure from any of them. Having said that I’ve never been with a man, not into macho dicks as I was abused when I was younger.

However, my companion was disappointed that I am not bisexual because we had so much fun with crossdressing and a strap on, she wanted me to experience feeling a penis throbbing and coming deep inside me. I could tell she really wanted this, the idea of watching me get screwed by a man made her extremely wet and I am truly someone that wants to fulfill her every fantasy. But this would be a huge leap for me and I once said jokingly that I’d need to be tied up and forced to submit to this or even sucking a cock. She seemed to accept that and the topic changed.

A few weeks later while playing, she’d fully and beautifully feminized me with full make up and nails, the works. I was dressed in new lingerie, stockings and heals, the look completed with a new black cocktail dress (My companion is a lady of means). I loved the way she’d made me over as she usually doesn’t go to such lengths but she too was dressed to the nines and seemed very excited, so was I. We both looked absolutely gorgeous and I though we might be going out. That too would be a first for me as I’ve never cross-dressed in public, but I looked very passable and was confident no one would recognize me. I was so wrong.

She led me to the spare room, as we entered I saw what she’d been up to, there was an ottoman, a tv and a few pillows, and arrangement of toys and lube and other things. She had me sit on the edge of the ottoman where she blindfolded me, it was padded and I could see nothing, then had me bend over and placed me into a humbler with my wrists shackled to the sides, made me kneel and tied down on the ottoman so that I could barely move.

She then lifted my dress and proceeded to play with my cock and balls while slowly stretching and lubing my butt hole before calling a friend to come over. She hadn’t mentioned she’d be having someone else over. The idea of serving two mistresses has always aroused me. Now she’s got a couple of fingers in there and I am really looking forward to her girlfriend arriving. She now has her strap on poking my ring and slowly pushing the tip in and out, going a little deeper each time, taking her time, distracting me, telling me her friend will be here shortly and I’d better make it worth while.

After a nice long pegging, giving her multiple orgasms and causing lots of messy drippings from yours truly, there’s a soft knock at the door, it opens and she says giggling, “oh you’re here, don’t say a word, get yourself ready and enjoy the show”.
I hear the rustling of clothes being taken off as she gets undressed and I wonder which of her friends she’s told of our games. I know them all and many are very attractive, it’s turns me on that now, someone will know what has been, until now, a very closely guarded secret and I won’t know which of her friends it is. She’s very quiet, they must have had this planned.

My rock hard dick is banging against the ottoman I’ve been tied to, I’m so turned on by not knowing which of her friends is going to join in and fuck me. She giggles and says, “I see you like what you’re watching, time for me to watch, trade places with me”. Nothing else is said. She moves out of the way and I sigh in anticipation. Then I feel the hard, lubed tip as I’m slowly penetrated. I gasp as it’s bigger than I’m used to, she must have brought a new one with her as although it’s big and hard, it feels soft and forming. My companion is now sitting with my face between her thighs, pushing her wet pussy onto my mouth for me to eat and holding my shoulders down with her silky thighs, calves and heels curled to my sides, holding my arms still while her friend starts to fuck me. It feels so good. I am completely at their mercy, cannot move except where she lets me. I’m in heaven, I have my butt filled by her unknown friend’s strap-on and my mouth is full of my companion’s juices. I have never felt this way, I’m getting everything I’ve ever dreamed of, my companion is coming in gushes, so I know what ever she’s watching is giving me the most delicious mouthfuls.

Then she says, “OK Garry, put your back into it and come in Tamsin’s ass”. I’m so surprised I buck, but I can’t move, her friend Garry isn’t holding back, now he’s grabbed my hips with a powerful grip and goes balls deep. He’s huge, his balls banging against mine that are restrained in the humbler. I can feel him getting bigger and building up. “I’m close he tells her. “Me too! I’m going to drown you Tamsin, make sure you drink it all” she says.

I can’t help myself; I cannot stop my erection. I feel myself building to orgasm too, there’s a guys cock in my arse and I cannot help but love it. I hate myself for liking it, but I love it and my companion loves it, I start to rock onto his cock as best I can until I feel him throbbing inside me. ‘I’m coming”, he shouts. “Me too” she screams. My orgasm explodes from me, I’ve never orgasmed from anal penetration, and I shoot my load down the side of the ottoman as we all cum together. He keeps pumping, keeps pounding me and all I can do is rock back and forth onto the still hard cock. My companion is quivering, orgasming over and over, drenching my face with her juices as she watches her slut of a slave reveling in the first real butt fucking of his life.

I thought she was about done with orgasming, she’d already cum more than I’d known her too before. But she’s watching Gary and he says, “I have another load for your sluts ass”. I can feel him building up again, my companion starts bucking on my mouth watching him ride me even harder than before. She starts to quiver and I can’t help but to start dripping as he pulls out and shoots his load up along my back. My companion, seeing this, exclaims, “you shot right over him onto me”. She starts squirting into my mouth and all over my face. “Oh my fucking god, that’s so fucking hot!”, she gasps while gushing more and more. Then grabs my blindfolded head and puts my mouth over where his juice had landed on her lower belly. “Lick this up my little slut”, powerless to refuse and not knowing what it was, I start cleaning her as she started squirting again watching me eat another man’s load. He grabs his clothes and leaves with a slap on my quivering ass.

“Well Tamsin, now you’ve been tied down and fucked by a man, the only way it could ever happen the first time, how did that feel? I told you there’s nothing that compares to a man coming in your ass” she croons, and the unexpected cum eating was the icing on the cake. I had put you in black to mourn the end of your straight life and believe me, this is going to happen regularly, I absolute love seeing you being fucked and I see you thoroughly enjoyed the experience too.”

She took off my blindfold, “I had set up a couple of Camcorders so you can watch the video of your de-flowering, now that Garry has gone, while I fuck the cum out of your ass and we discuss you learning to suck cock too; I’ll enjoy watching you swallowing cum from the source, and from todays experience I’m going to make sure you get a lot of practice and learn to love it too”, she said grinning wildly. I knew that she was right and that it will not be a ‘one off’ occurrence. “Yes mistress, what ever you desire mistress”, I whisper, totally exhausted and satisfied. “You called me Mistress; I like that! From now on that’s how you’ll address me when you bottom. Not that I think you’ll ever top again now, that was too much fun for me”.

I watch her, bleary eyed as she pulls out the biggest strap-on I’d ever seen, and I watch her put it on. “You took Garry easily, I consider him to be pretty well endowed, but now it’s time to stretch you for bigger things”. She looks down, and sees the mess on the ottoman. “Well, we’ll”’ she said. “That’s a huge load you squirted there. As you came by being fucked in the ass without being stroked, which reminds me…”,

She goes to the bag in the corner and takes something out and comes back. She removes the humbler and starts to put what feels like a ring around my balls and limp dick, she then adds something that feels like a tube and I hear a click. I think in future that you will only cum that way and we can lock that thing up. After today I don’t need it, I was completely satisfied today without that messy thing in me. It’s time for chastity and full time feminization. From now on you will be in chastity 24/7 Tamsin. Your transformation starts today.” Then, as if to re-enforce her decision, she starts to thrust her monster strap-on into me, I buck and protest, to no avail, I’m as tightly bound as I was when this started. She gets the head into my cum filled hole and I yelp. “Now, now, stop you’re whining, that was the hard part’, she giggled, “well maybe not, it gets thicker and you’re slick and well lubed”. She proceeds to push it ever deeper while she has the video of my cherry popping playing on the tv to watch as she breaks me in. Soon I’ll have you sucking huge cocks and taking them balls deep, because that’s what you were born to do for me, and if I want a cock, you can fluff it for me and clean up the mess after I’ve been filled with another man’s cum. How do you feel about that? I utter and almost inaudible, “yes Mistress”. “Good” she says. “I’ll make a few calls tomorrow to make appointments for breast implants and a few other refinement surgeries. With hormones you’ll look perfect in a few a few months”. I gulp, deep inside I feel the truth of what’s happening, and to be honest with myself, it’s what I always wanted…