My First Time Dressed as a Girl (PT 2) (Aftermath) - Sex Stories

My First Time Dressed as a Girl (PT 2) (Aftermath)

... cum. Eventually I swallowed reflexively and it must have been too soon. Gunther told me I was a very bad girl and must be punished again, pulling me across his lap and spanking me. It wasn’t as brutal as before and I thoroughly enjoyed it with the vibrator humming away inside me while he worked my tender ass with his bare hand. After my ass was pink and tender again, he stood up and I could see that the spanking had gotten him as excited as me as his cock was rock hard. I begged him to let me suck it and he consented but only for a moment. After a few minutes he pulled his cock away from me and told me it was time, leading me to the middle of the room he instructed me to get on all fours, doggystyle. He eased the vibrator from my ass and I felt a little pop as it came out; I squirmed and wiggled my ass a bit missing the feeling of it inside me. “Don’t worry slut, I’ve got something even better than that for you.” He paused for a moment to put on a condom and I idly wondered where he found condoms big enough to fit him. He must have guessed what I was thinking and he told me they were special order from a company in Europe. Then he applied more desensitizing lube to my hole and started working his fingers into me using them to stretch and widen his target. I was moaning in pleasure from this when he asked if was ready. I knew what he wanted from me so I wiggled my ass invitingly abegged him to fuck me like a good little whore. I felt the head press up against my waiting hole ...

... and he started to push it in. Even with the desensitizing cream and having been stretched by the vibrator and his fingers it was a tight fit and the pain was pretty intense he paused for a moment with just a few inches inside me to let me get used to his girth. Then slowly and inexorably he began working it deeper inside me with slow back and forth strokes, pushing it a little deeper each time. Despite his gentleness I gasped in pain a few times and was tearing up a bit. Tracey suggested to Gunther that he pull out for a moment and let me catch my breath as it had seemed to work earlier. He did so and after a couple of minutes the throbbing pain inside me subsided and I wiggled my ass suggestively begging him to put it back in me. It went in much easier this time and he slid further into me getting about seven inches deep before coming up against stiff resistance from the muscles deep inside me. I pushed back against him and he grabbed me by the hips and pushed forward harder, I could feel the clenched muscles starting to yield when all of a sudden I felt a sharp tearing pop and he thrust all the way inside me to the hilt. The pain made me cry out and he stopped just resting there with his huge cock buried in my ass and let me get used to the pain while my body adjusted to the intruder inside of it. After a bit he pulled back some and began thrusting back and forth slowly moaning as he did so. “ Gottdam your pussy is so tight Bobbi, it’s the tightest pussy I’ve ever had.” He ...