Dressed as a Girl

Published on May 6, 2012

Transgender

I'm Jimmy James and this is a story of cross dressing and sexual submission at the hands of my girlfriends father.

============================ Afternoon Delight

Once Bob caught his breath, he pulled out stood up and pulled up his pants without a word. He had a big smile as he stood over me.

"God you're a good fuck. Now go get me some coffee." he barked.

I cheerfully did as he asked. While I walked to the kitchen, my pussy was so squishy and wet. I could feel cum oozing down my legs. After seeing how good I looked in all the pictures. It gave me an unbelievably warm, rich feeling deep in my belly.

When I got to the kitchen, I wiped up the extra cum with a big smile. This was so good. I loved all the attention I was getting as a girl. The sex was great and I was getting more than I ever thought possible. Feeling cum run down my leg had turned into the greatest feeling in the world. It let me know I had done my job as a woman. I had spread my legs and given him the hot juicy pussy that he needed. No questions asked.

I walked back in with a big smile as I handed him his coffee. He had me get on my hands and knees in front of him again so he could admire my freshly used ass while he drank his coffee. I took my position and listened to him talk about how hot it was to see me with all those men. How happy it made him to be able to supply me with as many men as I could handle. How hard he got while watching me use them to get what I needed. What I always needed. Hot sex and stiff cocks.

I could feel my pussy twitching as I listened to him and watched my pictures flash by with comments about how much I need/loved cock. Then he slowed it down again to play and a short video of me at Milo's started to play.

"You gotta watch this. This is the sexiest thing I've ever seen." he said excitedly.

There was a close-up of my face as I greedily sucked cock under the bar. It pulled back to show a bar full of people. Bob was standing with a big smile as he talked to a guy next to him. I was sitting under the bar with my legs spread wide. My half hard cock, clearly visible. Then the guy groaned and began pumping his hips against the bar.

My cock got rock hard instantly. Cum drooled out and dripped from my balls. He continued to hump against the bar while groaning loudly. When he was done, he smiled at Bob and told him how good it was. While he finished what he was doing in my mouth, you could see my cock get soft again. When he stepped away, I had a big smile as cum dripped from my chin. Then it ended.

The whole time it played he talked non stop about how sexy it was to see how much I enjoyed myself. How hot it was to watch my cock get hard while I swallowed cum. How much he enjoyed it when I did it for him. How hard it made him to know how much I enjoyed doing it. How good it made him feel to give me a mouthful of cum or fuck me. How much it made him want to be with me when he saw how happy it made me to have sex with all those men. How much he wished he could be hard all the time so I could suck his cock and give him sex 24/7.

Hearing all the praise while watching myself in action was such a turn on. I could feel cum leaking out my cock and making my pussy sloppy wet again.

As soon as it was over, Bob grabbed the remote and started the real time video of the photo shoot. I watched for a second as I walked in. Stripped nude in a room full of fully dressed people. Was introduced as the model and said hello to everybody like it was an everyday thing.

My pussy was wet again and I knew I wanted more sex. I turned to look at Bob with a smile. Pulled out his cock and began sucking it while looking up at him. He just sipped his coffee and smiled while he watched.

"That's my girl. That's what makes you the best pussy in town. You're always ready for more." he said as he smiled down at me.

I giggled and started sucking his soft cock harder and faster.

"I know how much you need sex. So I called for back up while you were getting coffee. I hope you don't mind." he chuckled.

The image of me sucking Buddy's cock while he watched flashed through my head.

"Not at all." I responded cheerfully.

"Good girl. He should be here any time now." he smiled.

Just as I started sucking his cock again, the doorbell rang.

"Perfect timing. Go let him in." Bob told me with a smile.

I cheerfully pranced over to the door expecting that when I opened it I would see Buddy standing there. I was shocked when I opened the door and saw Jake smiling back at me. I stood dumbfounded for a second and was acutely aware of my nudity. My confidence was bolstered when I looked down at myself and saw a nude woman.

"Hi. I'm Kitty. You must be Jake. Come on in." I said with a smile as I shook his hand.

By the time he stepped in, Bob was already standing next to me.

"Hi Jake. Good to see you again. Glad you could make it." he said as he shook his hand.

"Me too. I can't tell you how happy I was to get your call." Jake told him enthusiastically.

"Well good. Like I said on the phone. Jimmy took care of everything. For the next two hours. She's all yours. Her favorite position is missionary. She loves to swallow and she can't get pregnant so don't be shy about cumming inside her. She loves that too. You kids have fun." Bob chuckled as he walked out.

I blushed as I looked at him. I took him by the hand and led him to the bedroom. Once inside, I told him to strip while I put in some porn. When I was done I turned to see him laying nude on the bed. There was a brass ring around his cock and balls. I sauntered over, sat next to him and began stroking his already hard cock.

I was so turned on, I could hardly breathe. It felt so good and I had wanted it so badly. It was hard to believe, I was finally getting my chance. I was actually sitting next to my best friend stroking his cock without him knowing. This was perfect.

"What's this for?" I asked as I played with the brass ring.

"That keeps me hard for as long as I want." he told me.

"Cool." I giggled as I started sucking.

I sucked him long and slow while he sat back and watched with a smile. I forced him down my throat. I luxuriated in the way it made me feel to have his balls pressed tight against my chin while his fat cock was deep in my throat. I began bobbing on his cock. His balls bouncing against my chin every time.

The feeling of my best friends cock driving down my throat like that drove me wild. I wanted to swallow his cum worse than anything. I sucked his cock hard and fast. I kept it up until I felt his cock throb hard and my mouth filled with cum. I quickly swallowed while looking up to see his face while feeding me his family seed. I watched him the whole time he twitched and groaned while swallowing everything he could pump into my mouth. Seeing what I was doing for him made me so hot, I was about to cum.

The instant he relaxed, I straddled his lap and sat on his cock. I groaned with pleasure as I felt him drive deep inside me. I thought about all the times he had told me at the office how sexy he thought the pictures were. How bad he wanted to fuck me because of them. The workout his wife was getting because of it. How hot it made me to hear about it. How good it made me feel to know I was giving him something we both wanted so badly. The whole thing was such a turn on, I felt a small orgasm ripple through me.

I squeaked and jerked through my orgasm, while squeezing my tits. Then I began riding his cock like I was on the last dash for the triple crown. I drove his cock into me as hard and fast as I could. I couldn't help but to smile as I listened to the loud wet slapping noise every time I drove him deep inside me. Feeling my tits bouncing wildly while I rode him hard was giving me the thrill of a lifetime. I couldn't even imagine anything making me feel as good as I felt right now.

I was so thankful I had decided to do this. Playing the part of the girl was easy. I knew exactly what men wanted from me. Giving it to them got me all the sex I could handle. Being able to dress up and do this for so many men without them knowing was fun. Doing it for my best friend was the ultimate sexual thrill. My purpose was so clear and the sex was so good. I loved everything about it. Bob was right. This was exactly what I needed.

I was riding Jake as hard as I could. He began to drive his hips up to meet my downward thrusts. It felt so good I squealed with delight. We did that hard and fast for about five more minutes. We were both so worked up his cock popped out. I was so close to orgasm, I just about freaked out trying to get it back in. I wanted it inside me so bad, I couldn't get it in fast enough. The instant it was back where it belonged, I resumed my frenzied ride on his cock.

Not long after that, he began to twitch and groan under me. I was so close to my own orgasm, I barely noticed. I drove my ass down relentlessly until my orgasm finally overtook me. I jumped and squealed like a mad woman. My sweaty nubile body convulsed with pleasure while he watched with a smile. By the time it was over, I was so exhausted, I rolled off him and tried to catch my breath.

"That was fucking amazing! I wish my wife could fuck like that!" he laughed as he watched me panting desperately.

"Thanks... Jimmy said you were his best friend, so I should give you all I have. I hope it was as good for you as it was for me." I giggled brightly.

"It sure was. Is missionary really your favorite position?" he asked as he began to finger me.

"Yeah" I smiled while spreading my legs.

"Good.... You don't mind if I drive for a while do you?" he asked as he climbed on top of me.

"Not at all. I'm all yours." I told him as I anxiously watched him stuff his cock back in.

He got comfortable on top of me. Then began pumping into my over heated pussy slow and easy. My pussy was twitching wildly as I thought about how good this was. My best friend was on top of me. Inside me. Fucking me like a girl. I had fantasized about it a million times but the reality was much better than the fantasy. I had wanted his cock so bad and now I had it inside me. This was so good.

"For the next two hours you are. Is it true Jimmy took care of everything? How much did it cost?" he asked.

"He sure did. It's free. I volunteered." I told him with a smile as I wrapped my arms around his shoulders and my legs around his waist.

"No kidding?" he asked incredulously as he continued fucking me.

I giggled and blushed.

"Well yeah. Any friend of Jimmy's is a friend of mine. Besides, he told me how hot you were for me a million times. That you've been visiting the restaurant all week with your friends. That you liked it so much you were planning on visiting all next week too. Plus he told me how you've been sexually abusing your poor wife because you want to fuck me so bad. After hearing all that, I begged him to set us up. If anyone deserves to get a free sample of the best pussy in town. It's you. All I ask is that you tell all your friends. I'll be at the restaurant for lunch all week and at the club every night until Saturday." I told him cheerfully.

"I sure will." he groaned as he began fucking me hard and fast.

For the next half hour he fucked me silly. I was so turned on by being fucked by my best friend, I came three times. It was incredible. By the time he finally emptied his balls inside me again, we were both exhausted. We laid side by side on the bed panting and breathless. I couldn't help but to notice his cock was still hard after all that and couldn't take my eyes off it. It was hard to believe that after all we had done, he was still hard. It gave me a new appreciation for the cock ring he was wearing. I knew I had to get one before Cindy got home. I reached over and stroked his cock playfully while I admired it.

"Do you want a coffee, beer, or juice or something to drink." I asked while I continued to stare at his cock.

"Yeah, a beer would be great." he told me.

"Cool" I giggled as we both got up and headed to the kitchen.

He sat at the table while I got the beer. I handed him one and smiled as I openly admired his still hard cock.

"Let me take care of that for you. I would hate for that thing to get cold." I said as I straddled is lap, positioned his cock and sat on it.

We talked about the weather, how much we like sex and a bunch of nothing while drinking our beer. I was grinding his cock into my pussy the whole time. It was so relaxed to be just sitting and talking while we did this. The best part was that it felt so incredibly hard inside me. I couldn't have asked for anything better. As we were finishing our beers, I asked if he wanted another. He smiled and squeezed my tits.

"No, I only have 2 hours. I want to fuck you some more." he said as he laid me back on the table and spread my legs wide.

We both watched as he stuffed his cock back in. He watched my tits jiggle and bounce as he fucked me hard. I squealed loudly as he brought me to two more orgasms. When he was almost ready to cum, he pulled out and shot his load all over my belly. He watched closely as I scooped it up and licked it from my fingers. When I was done, he grabbed two more beers and suggested we head back to the bedroom. I agreed and admired how hard his cock was as we walked.

When we got to the bedroom, I had him get comfortable on the bed. I climbed on top of him and sat on his cock again. I ground on it hard while he watched porn. As soon as he was ready, he fucked me missionary style again. Then I rode his cock some more. We spent pretty much the entire two hours with his cock stuffed deep in my pussy. It was the best two hours I had ever spent.

I admired his cock as he got dressed. I commented on how much I liked what the cock ring did for him. How lucky his wife was to have someone that could fuck for two hours straight. How I understood now why she was so worn out from all the attention. He chuckled while pulling out $200 and dropping it on the night stand.

"No, No.... I already told you. It's on the house." I said as I tried to give him his money back.

"Consider it a tip then. You were great and I really want you to have it." he said as he put it back on the night stand.

"Thanks" I giggled as I blushed brightly.

I had such a warm feeling of accomplishment as I laid there. I couldn't have imagined a better way to spend an afternoon at home. Just as I was getting out of bed, we heard Bob at the front door.

"Times up!" he yelled.

I giggled, grabbed Jake by the hand and led him to the door. Bob had a big smile as he watched us walk in. It wasn't until I noticed him looking at my pussy that I felt cum running down my legs. When I looked down, I watched as cum dripped from my pussy lips. A big chill ran down my spine as I thought about what my best friend had just done to me. It was proof of how successful I had been at playing the part of the girl for him. It made me feel so good, I made no effort to hide how happy I was about it.

"How was she?" Bob asked pointedly.

"Oh God... She was great. She's a sexual dynamo. Thank you so much for setting this up for me." Jake beamed as he shook Bobs hand.

"Don't thank me. Thank Jimmy. If it weren't for him, none of this would have happened." Bob responded as he gave me a sly grin.

"I sure will. Thank you just the same. And thank you Kitty. You were great." Jake told us with a smile as he headed out the door.

I was so thrilled about what I had just done, that I could feel my pussy twitching as my cock strained to get hard.

"Did you have fun?" he chuckled.

"Fuck Yeah. I had a great time. I wasn't sure about it at first, but once we got going, I had a great time." I tittered excitedly.

"That's my girl. Now march that hot little ass back to the bedroom, so I can fuck the shit out of you while you tell me all about it." he ordered.

"Gladly." I said with a smile as I headed back to the bedroom.

Bob followed close behind while telling me how sexy I looked with fresh cum running down my legs. How much he enjoyed fucking a freshly used pussy. What a turn on it was to spread my legs and see nothing but a little pink meat hole waiting for him. That I looked, felt and acted so much like a girl that there was no way to tell the difference.

How glad he was that he had turned me into a girl so we could do this. He said the biggest thrill for him was to see that I enjoyed it as much as he did. He told me how he loved seeing me get fucked by so many men. That he had made it his mission to make sure I got fucked by as many men as possible before the girls got home. That he was going to do his best to make sure all my sexual fantasies came true while he did it.

Hearing all that made me want his cock so bad. As soon as we were in the bedroom, I laid on the bed with my legs spread. I watched silently as he stripped while staring at my pussy. I had a big smile as I watched his hard cock swing around while he got on top of me. We both watched anxiously as he easily stuffed it balls deep into me.

"Oh god.... You wouldn't believe how good this feels. You are such a hot little pussy." he whispered passionately.

"I'm the best pussy in town." I whispered back as he got comfortable.

"Good Girl... Now tell me all about what you and Jake did while I was gone." he groaned as he began pumping into me.

I began by telling him how glad I was that he had invited him to stop by. I told him about the cock ring and that he had been hard the whole time. I talked about sucking his cock. How exciting it was to know that I was sucking my best friends cock. How exciting it was to know that my best friend was watching me suck his cock. How good it made me feel to do it for him. What a thrill it was for me to watch his face while he came in my mouth. How much I enjoyed swallowing for him. How much I was looking forward to hearing about it when I went back to the office.

Every time I said what turned me on about my time with Jake, Bob would whisper 'good girl' in my ear and fuck me a little harder. I always laid it on thick about what I liked best about it.

As I continued my story I told him everything we did in explicit detail. How good my orgasms were. What a turn on it was to be able to let my best friend fuck me without him knowing. How sexy it made me feel. How much I enjoyed the sex. How much I enjoyed being able to do it for so many men. How much I was looking forward to seeing how many men I could be with before Cindy got home.

Bob called me a 'good girl' at least 50 times. Plus he fucked me so hard, I came two more times. It made me feel so good, I could hardly stand it. By the time he dumped his load inside me, I was so exhausted, it only took a couple of minutes for me to drift off to sleep.

Next: Chapter 31


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