First part: Here
I had Sally make the change permanent after my second night with Rob. It was clear that even without the little surprises Sally had left in my psyche that I was just more comfortable as a woman. I’m sure it helped being a sexy blonde, but that’s beside the point. It was an adjustment, of course. For one: Rob and I didn’t have sex for literally over a month. Now, we weren’t celibate. I was sucking his cock at least once per day, and almost always more. I get such thunderous orgasms from milking his meat with my lips that it wasn’t necessary to do anything else. Of course, I started to get curious. After 40 straight days (I counted) it was time to let Rob have my virginity. And what better way to do that than to surprise him at work? He had a nice, big office to make my first time memorable.
I was jittery all the way to Rob’s work. I was excited to finally indulge my feminine self, to do something that would have been impossible as a man. I wore a slutty office outfit to really complete the afternoon. I enjoyed dressing like this anyway, the attention was so arousing. Rob was surprised to see me, but he caught my drift when I locked his office door. “Sir, I’ll do anything to save my job,” I said to tease him. He grinned and beckoned me over. “It’s my first time,” I tried to play innocent, suppressing a giggle. I stripped to my underwear, kneeling in front of him. I could tell Rob was confused. “You’re really big, baby, let me get you good and wet first. When you’re ready just force me where you want me. Take me, baby.”
I slipped his cock in my mouth, the familiar heat once again making me cream myself. Everything about sucking cock turned me on, especially Rob’s monster. I moaned as his hard flesh passed between my lips and down my throat. It felt so good. I couldn’t be too loud with his coworkers close by but it was exciting to be doing this somewhere besides our place. He held me down, enjoying my mouth so much I thought he wouldn’t make me do anything else.
After a few minutes of slobbering and gagging on Rob’s excellent he cock he picked me up. I giggled as he turned me around and set me by his desk, bodying up beside me and picking my leg up to expose my quivering womanhood. He tore my panties free, now only wearing my shirt bunched underneath my tits and my pantyhose. He pushed his swollen cock head between my legs, teasing my waiting pussy. It dragged over my wet lips and I prepared myself to be finally be penetrated. I moaned softly for him, meeting his gaze. He pushed forward and I felt him prod my entrance, but he slipped back a little and I felt his dripping head tease my backdoor. Rob thought he was lined up and before I could say anything he shoved his hips forward and immediately went balls deep in my asshole.
“Fuck!” I shouted as the hole stretched for Rob’s giant cock. He moaned, realizing his mistake, but he didn’t seem concerned. He bulged between my cheeks, a heaving mass of lust, wet from my mouth. The sensation was odd and alien to me and naturally a little painful. Rob was holding me tight and I went limp in his arms. I kept waiting for him to pull out but he didn’t. “Sorry, baby,” he whispered, squeezing one of my generous breasts. He wasn’t apologizing for the accident, I was soon to learn, but for what would come next. He started fucking me, stretching my little asshole with hard, rhythmic thrusts. It was unlike anything I’d ever experienced. He knew I couldn’t stop him and that seemed to make him more bold. His hips slapped loudly against my ass as he started to fuck me harder and harder. He was insane with lust. I felt it reverberate in my ass as he grunted with effort. He shoved me on his desk and kept going, holding my shaking legs for balance.
The look on Rob’s face was pure ecstasy, driving his cock into my ass harder and harder. I felt like I was going numb, wishing I had just sticked to sucking him off. I was trying to be a woman and pleasure him the way only a woman can but instead I was being butt fucked on his desk. It was hard to breathe, the heaviness of his manhood inside my ass the only thing I could focus on. Our eyes met for a moment and the absolute pleasure in his face turned me on a little. It was almost like when I sucked him off, the same heat but directed at a different part of me. He was watching his cock impale my asshole, clearly enraptured by it. As I watched him I felt a peace settle over me. This was okay. Rob was my boyfriend. He provided for all my needs. I should return the favor, even if he needed my asshole. “Does it feel good, baby?” I moaned for him. It was all for him. “Fuck yes!” He grunted. “Are you going to cum in my slutty little asshole?” I said in between breaths. It felt like he was expanding inside me. “No,” he stuttered, “your face.... walk out with it.. I knew what he meant. “Give it to me, baby,” I moaned, “I said I’d do anything.”
It wasn’t much longer. He stumbled backwards, popping free from my now-gaping asshole. My guts felt like they had been scrambled. I dropped obediently to my knees, ready to suck him off. He aimed his cock at me and came, the sticky load exploding against my plump lips. The thick load dripped down onto my naked tits as the last ropes of his orgasm landed on my face.
We were silent for a moment. Rob was struggling to catch his breath, still rock hard in my hand. “Do I get to keep my job?” I teased with a smile. “If you don’t wipe that off until you get home,” he said mischievously. I got dressed as best I could and blew him a kiss goodbye. His coworkers pretended they didn’t notice me so I knew they were totally aware of what we were doing. I wasn’t ashamed of the cum on my face. It was a little weird to walk after having a giant cock shoved up my ass so hard but I managed. If this is what it took to make Rob happy I would do it. He was going to have to cum in my mouth a whole hell of a lot to make up for this little accident. And he was going to fuck my pussy real soon.