All the Way (Part 1) - Sex Stories

All the Way (Part 1)

... very well lubed and so was the dildo, when Kathy drove it into me it stretched and hurt me more than ever. I whimpered as the initial shock of being so roughly entered registered in my brain. “Take it slut! You know you love my big, hard cock fucking your tight fucking pussy! Say it, Brenda! Tell me how much you love it!” “Ooohh, I love your cock in my pussy! I want to feel you cum inside me! Fuck me! Oh fuck my pussy hard!” Kathy fucked me like never before, driving her hard cock into me faster and faster. When she hit bottom it hurt as well as feeling so absolutely wonderful. Over and over she hammered into me until I felt my own little dick spilling its seed which quickly filled my hand. As always I licked my hand clean while she continued to pump in and out of my ass. Then something entirely different washed over me, a feeling that had no comparison. This feeling was so much better than my orgasm had been and it seemed to go on forever and ever. Totally lost in my new, wondrous feeling, I was brought back to earth when I felt Kathy tense and then slam her cock into my as deeply as she could. Seconds later I could feel the fake sperm blasting into me and that sent me spinning completely out of control. “Yesss! Yesss!” “Take it all, you fucking little whore!” After a few more strokes Kathy pushed forward and we collapsed on the bed in a heap of satisfied flesh. Even though I always came when Kathy fucked me, nothing could even come close to the way I had cum tonight. When ...

... Kathy and I went out the next Friday night I was both thrilled and scared. She chose a very calm and quiet bar and grill not too far from home. This was my first time out in public dressed as a woman, not counting the walk I'd had earlier in the week. Tonight I would be interacting with the waitress and then we'd see if I could pull this masquerade off. I needn't have been so worried because everything went off without a hitch. The voice training discs Kathy had purchased had done their job quite well. We had a couple of drinks, a very nice meal, and then a couple of more drinks, one of which was paid for by a man at the bar. That was the first time a man had ever bought me a drink, but something told me it wouldn't be the last. Almost a year passed after that and our excursions grew more and more frequent. Not just out for a drink and a meal, but shopping as well. My wardrobe increased as did Kathy's, both of which included numerous very sexy dresses and more heels than I could shake a stick at. One thing I did notice was that my masturbating frequency had dwindled down to maybe once every couple of months, unless she wanted me to jack off in front of her, but that was cool. I didn't miss jacking off a bit mainly because Kathy demanded sex of some sort almost every night, except when she was having her period. When she was on her period she decided that I needed to have one also, as in wearing a tampon in my ass pussy and changing it daily. Kathy also decided that I should be ...