I'm Jimmy James and this is a story of cross dressing and sexual submission at the hands of my girlfriends father.
============================ Tuesday
All night, I dreamed about what my friends cocks looked like as they stuck them through the hole. How good it felt when they came in my mouth. How good their cum tasted and the satisfaction I got from swallowing for them. Mostly I dreamed about the look on their faces while I laid on my back with my legs spread. How good it made me feel to have them on top of me while they fucked me. When I woke up, my pussy was soaking wet and my cock was straining to get out of it's prison. I needed to cum so bad, that I wished there was a man there to fuck me.
With no other options, I spread my legs wide, rubbed my pussy frantically and fingered myself hard, while I fantasized that my friends were there. Taking turns at giving me what I needed, while the others watched. When I finally came, I basked in the warm glow of my fantasies. I reflected on how sexy it made me feel to have all five of them fuck me in one night. How much I enjoyed spreading my legs and letting my best friends fuck me like a girl. How good it made me feel to wrap my legs around them while they laid on top of me, grunted in my ear and filled my pussy with cum.
When I started to get turned on again, I blushed, got a quick douche, and went to make coffee. I opened the curtains and got the coffee maker ready. No sooner did I turn it on and get my cup out than I heard a light tapping at the door. I turned to see Ed standing there with his robe open. I giggled, admired his swinging meat and slid the door open to let him in.
"Good Morning, Come on in." I said with a bright chipper smile while stroking his cock.
"Good morning. Don't mind if I do." he said as he reached down and caressed my pussy.
He walked in, took a seat, spread his legs and opened his robe with a big smile. I smiled back, got to my knees and started sucking. After everything that had happened yesterday. Having a thick piece of man meat in my mouth was making me hot. I could feel my pussy twitching with excitement. Without thinking, I reached down and began to finger myself again.
I sucked his cock slow and easy. I eased it down my throat, pressed his balls against my chin and looked up at him. He had such a big smile as I eased the head in and out of my throat while stroking the shaft with my tongue. Seeing the look in his eye made me feel so good. I continued to suck it slow and easy. Luxuriating in the way it made me feel to look up and see a man that appreciated what I was doing for him. It made me think of Jake and the guys telling me how much they enjoyed my services at the hole.
Without thinking, I began to suck his cock faster while rubbing my pussy harder. I began to think about how much I enjoyed sucking his half hard cock. How good it felt in my mouth. How effortless it was to slide it down my throat. It made it easy for me to work the whole shaft instead of just the head.
It didn't take Ed long to respond to what I was doing either. After only a couple of minutes of that, he groaned with pleasure and filled my mouth with cum. I deep throated for him as quick as I could. I looked up at him again while his cock throbbed in my mouth and throat. Between the look on his face and feeling cum shooting down my throat, I felt a small orgasm ripple through me. My pussy squeezed, pulled and sucked at my fingers. It was amazing.
I sucked the head for a little while longer while I watched him relax and smile down at me. Then I got up and poured us both a cup of coffee with a big smile. When I was done, I sat down and made a show of squeezing and massaging my tits for him. He smiled back and watched me closely the whole time.
"Wow.... This really is fun for you isn't it?" he asked as he reached out and began playing with my tits.
"It sure is. This is the best thing I've ever done. It really makes my day to know that I can have so much fun, making so many men feel so good." I said as I pushed out my chest for him.
"Well I'm happy hear it. It makes my day to know that you enjoy being here to make me feel this good every morning." he said as he sat back, raised his cup to me and took a sip.
I blushed brightly, looked down at his cock then looked back at him and raised my cup to him. "Thanks"
He chuckled at my reaction. "So.... Tell me what you did yesterday. Did you do anything fun?"
I smiled brightly and began my tale. I told him how excited I was after he fucked me yesterday. How it made me want to go to work as soon as he left. How when I did finally get to work, Jimmies friends were there waiting for me to start my shift at the hole. That they had flashed their ID's through the hole before letting me suck it for them. What a turn on it was for me to know who's cock I was sucking. How good it made me feel to swallow for them.
I told him about going to the club and getting fucked by Buddy first thing. Then waiting tables in the nude. How excited I was to be nude in a room full of horny men. How good it was for business and how much I made in tips.
When I saw his cock begin to get stiff again, I reached out and began to stroke it gently. I stared at it mesmerized by the way it looked and felt in my hand. As I told him about Bob stopping by with Jimmies friends after work. He put a hand on my head and began gently pulling me toward his cock. By the time I finished telling him how sexy it made me feel to know that all five of them wanted to fuck me. I was on my knees sucking his cock while he whispered about how good it felt. I was so encouraged by hearing it, I cheerfully sucked his cock hard and fast until he blew his load a second time.
"God, that was good. It's hard to believe such a pretty girl could have so much fun sucking my cock." he said with a grin as he watched me suck the head.
"Thanks. Want some more coffee?" I giggled as I stood in front of him nude.
"No, I need to take my wife out shopping." he said as he got up and stood by the door.
"Ok. Have a nice day." I giggled.
"Well, thanks to you, it's off to a good start." he chuckled as he walked out.
I blushed as I felt that warm satisfied feeling wash through me and went to take a shower. Becoming a girl was the most sexually satisfying thing I had ever done and making men cum was the best part of being a girl. While I showered, I thought about how good I felt about myself as a girl. How natural it had become for me to let men use me like a girl. How much fun it was to be able to have sex with so many men without them knowing. How sexy it made me feel to have sex with the men I knew from work. How special it made me feel to be able to provide those services to my best friends and my neighbor. How happy I was to be getting along with Bob because of it.
I squealed with delight and watched my tits bounce wildly while I jumped around. I luxuriated in how good it felt to have tits and how feminine they made me feel. I soaped up and caressed my pussy lovingly while thinking about how much fun it was to have a pussy. The satisfaction I got from letting men use me like a girl. How good it made me feel to spread my legs and provide them with the pleasures of being with a girl. I shuttered, jerked my hips and almost fell over when an orgasm swept through me. I had a big smile as I pictured my friends faces while I sucked their cocks at the glory hole.
When my orgasm ended, I cheerfully finished my shower thinking of Ed, Bob, Buddy, Jake, the guys from work and all the things I had done for them.
While I dried off in front of the mirror, I blushed at how happy it made me to do it. How sexy it made me feel to be able to do it. How much I enjoyed being a girl because of it. How satisfying it was for me to let them use me like that. How anxious I was to get to work so I could do it again.
Thinking about it made my pussy so wet, I had to do something. I quickly headed to the dressing room. Strapped in the hula vibe. Turned it on high. Put in the video of me at Milo's bar.
I sat on the arm of the sofa and began grinding my pussy against it. I watched how hard I got while sucking cock under the bar. I watched while I was strapped into the buffet table. I watched as men lined up to fuck me. But the real turn on was watching the biker 'girl' pull out her cock and start fucking me. No sooner had it started than I came so hard, I almost blacked out. My whole world lit up with pleasure. Next thing I knew, I was on the floor kicking and squealing about how good it felt. It had to be the best orgasm I ever had.
After that, I put the hula vibe on random. Drank coffee and cleaned the house with a big smile. I couldn't wait to get to work so I could suck my friends cocks again. The thought of them and all of the other guys at the restaurant sticking their cocks through a hole in the wall so I could suck on them was electrifying. I had never imagined giving men that kind of pleasure could be so satisfying for me, but it was. In fact, giving men sex is what made dressing like a girl so much fun. While I got dressed for work, I couldn't help but to think about how much I was going to miss it when Cindy and her mom got back.
On the way to work, I turned the hula vibe on high and smiled as I thought of the days I had ahead of me. What a turn on it was to feel my tits bouncing all the time. How much fun it was to flash my pussy and spread my legs for horny men. How many times I was going to get fucked. How many cocks I was going to suck. The gallons of cum I was going to swallow. Being a girl was so much fun, I didn't want it to end.
When I got to work, I strutted in with a big smile. Bob met me at the door and ushered me over to a table. He stood me in front of my friends while I stood quietly and blushed. He stood behind me, pulled up my skirt and exposed my pussy to my smiling friends.
"Kitty, Jimmies friends want to thank you personally for seeing them last night and tell you how much they enjoyed it." Bob said.
They all mumbled their agreement and said how good I was. I could feel my pussy twitching while the hula vibe was dancing inside me. I just smiled and gratefully soaked in the praise.
"Well, Thank you. I enjoyed it too. I can't tell you how glad I was that you stopped by. It was just what I needed." I replied graciously while pulling up my top and shaking my tits at them.
They all chuckled and thanked me again. I giggled, pulled my top back into place while Bob chuckled and let go of my skirt. While we walked away, Bob pulled up the back of my skirt and smiled at me.
"I can see why you like doing that. It was fun. I wish I could be there when they tell Jimmy what you did." Bob chuckled.
I giggled and blushed. "I know. I can't wait."
"Good Girl. Now get to work." Bob said as he watched me go into the ladies room.
I waited for the girl at the hole to finish. I quickly stripped down and took my place at the hole, eagerly sucking cock. Jake and the guys showed their company ID's. So did a bunch of other guys. I recognized all of them and eagerly swallowed for all of them. Once again about half the guys that used the hole were guys from the office. It was such a turn on for me to suck their cocks. That between that and the hula vibe. I came four times. It was awesome.
When I was done with my shift. I quickly cleaned up the hula vibe. Put it in my purse. Fixed my makeup. Went to the club and begged Buddy to fuck me before I got started. He of course, eagerly agreed and fucked the hell out of me. I had so much fun giving lap dances and getting fucked in the back rooms. That the whole afternoon just flew by. Next thing I knew I was nude at the hole under the stage, happily sucking cock like there was no tomorrow. I began to think about how nice it was of Bob to help me satisfy my new found need for cock now that I was a girl. The special thrill I got from sucking his cock and giving him sex.
Just like the rest of the day. The two hours I spent sucking cock at the hole was over before I knew it. No sooner had I gotten into a good rhythm, than Gloria was there to take my place. She was wearing a short skirt. Lace panties. A form fitting floral top and 3 inch heels. Her face still looked vaguely masculine, but all in all, she was quite sexy. I continued to suck cock while watching her get undressed. Once she was nude, she was all woman. She wasn't very pretty, but her tits and pussy looked so real. It was amazing. She watched closely as the cock I was sucking throbbed in my mouth while I gulped down the cum.
When I was done, we said hello. I told her how nice she looked and asked why she was walking funny. She smiled at me and blushed brightly.
"Well, I got here early so Buddy took me to a room and now my pussy is sore." she explained.
"Yeah, he does that. You'll get used to it. He's great isn't he?" I giggled back.
"He sure is. He says you and I are his special snake handlers. He says good pussies are hard to find and it's not often you find girls that can handle a cock the way we do." she said with a big bright smile.
"Yeah, we're quite the pair." I giggled.
Just then, a cock poked through the hole. Gloria smiled, put in the soft tooth guards and eagerly started sucking. I watched her closely while I got dressed. I watched her tits bouncing wildly as she greedily sucked cock. She was obviously enjoying what she was doing. It was hard to believe that I knew a guy that liked being a girl as much as I did.
I walked behind her and looked closely at her pussy. It was sloppy wet and I could see cum drooling out of it. I reached out and stuck two fingers deep inside her. It was so tight, juicy and velvety soft that I wished I had a cock so I could fuck her and find out if it was as good as real pussy. It was the first time since Cindy left that I missed having a cock.
On the way out, Buddy flagged me down and told me Bob was at my house waiting for me. I smiled, thanked him and cheerfully headed home. When I got home, Bob was sitting on the couch watching my videos and greeted me warmly. I stripped nude, put all my clothes and the hula vibe away. By the time I was done, Bob had his cock out and smiled at me. I smiled back, got to my knees and started sucking.
"Good Girl. I see you wore the hula vibe to work today. Did you like it?" he asked.
I groaned to the affirmative around his cock and smiled up at him.
"Good, I'm glad. That's Mary's favorite toy. She gave it to Cindy for Christmas. It's good to see you're putting it to good use." he said as he smiled back.
I was sucking his cock hard and fast when he grabbed my head and began fucking my mouth. He forced his cock down my throat with every thrust. After only a few seconds, he mashed my face against his belly and blew his load deep in my throat while groaning about what a good girl I was. Once his cock stopped throbbing, he let go of my head and breathed heavily while smiling down at me. I continued to look up at him and suck his cock slowly while it softened in my mouth.
"God, you're good at that. You were always good, but all the practice you got sucking cock at the hole really paid off. Having you at the hole has been really good for business. Plus I'm getting the best blowjobs I've ever had." he said while caressing my cheek gently.
I licked and kissed the head of his cock playfully while blushing brightly. It was hard to believe that hearing how much he liked the blowjobs I was giving him could mean so much to me. But it was the most rewarding thing he had ever said to me.
"That's why I'm the best pussy in town." I giggled while licking his balls.
"It sure is. Now go take off the wig, makeup and tits. We've got things to do." he chuckled back.
I sprang up, did as he asked and walked back in wearing nothing but my pussy panties. Bob snapped a picture and smile real big at me. Then he had me turn around, bend over and smile. When I did, he snapped another picture.
"Perfect. There's some stuff sitting on your bed. Go put it on. We're going out." he boomed.
I went to my bedroom and on my bed was a full Scottish outfit. Kilt, shirt, sash, knee high socks, shoes. Everything. I quickly put it on and walked back to the living room. Bob had me walk around a little and pull up my kilt to flash my pussy. Which I did without question. He cheerfully snapped a few pictures while I did.
Then he ushered me out the door and we were off to town. We went to dinner where he took a few upskirt/upkilt pictures while at the table. He took a few of me with my legs spread and kilt pulled up. A few more at the bar flashing my pussy while people stood behind me unaware of what was going on.
Then we walked around town and he took pictures of me flashing my pussy on the street. In the park. On the bus. Always making sure there were people in the background. He had me spread my legs or bend over while people looked at my pussy and fingered me in public. Then he talked me into sucking a guys cock in an alley while he took pictures. Always making sure that my pussy was in plain sight while I did it. He took me to the library and had me pose for him wearing nothing but shoes and socks. When a guy stumbled onto us, Bob talked him into taking pictures while Bob and I fucked. Then I gave the guy a blowjob for helping us and we went back home.
On the way home, we talked about how much fun we had. Bob told me he had always pictured me as a guy with a pussy and doing all the things we had just done. He also told me how hot it was to see it for real and thanked me for helping to make one of his fantasies come true. I giggled and told him it was my pleasure. After all he had made a good many of my fantasies come true.
Bob told me since I had been such a good girl, that when we got back to my house I was to take off the pussy and put on a suit like a real man. That Buddy and Gloria were going to stop by and he was going to let me help the two of them get her broken in as a girl. That way she could make some extra money at the club. I just about squealed with excitement and eagerly agreed. The thought of fucking her and finding out how good my pussy was, made my pussy wet.
The instant we got to my house, I ran to the changing room, stripped nude and took off my pussy like I was told. Bob had me strut around in the nude while asking if I was going to be ready to fuck 'Glory Hole Gloria'. He watched my cock get hard while I told him how anxious I was to fuck a girl like me so I could find out how good my pussy was. Bob laughed, looked at my cock, called me a good girl and told me to put on a suit. I smiled ran to the bedroom and got dressed as quick as I could.
When I walked back into the living room, Bob was putting in a new video of me called 'My Best Friends Girl'. It started with Jimmy standing nude in the changing room. Putting on everything I needed to become Kitty. Then getting dressed and walking into the restaurant. Then Jake pulling his cock out while standing in front of a hole in he wall. Then a side by side of me kneeling in front of the hole with a smile. Him standing in front of me separated by a thin black line. It was cut so well it looked like there was nothing between us. He pressed tight against the thin black line. He poked a business card at me, I took it, smiled real big and started sucking his cock furiously. I continued sucking until his cock began to throb in my mouth while he groaned and humped at the thin black line. Then I watched as he smiled down at me, put his cock away and walked off.
Watching it made me so hard, I could hardly stand it. It was the first time I had sucked his cock and it was an amazing thing to watch. It looked like Kitty was kneeling in front of him sucking his cock and swallowing his cum with nothing between them. When she was done sucking his cock, the look on his face is what really got me going. In the whole time I've known him, I had never seen him look so happy. It was incredible.
Next came the same side by side scene of me sucking his cock at the club. There was a girl dancing over my head. Grinding her pussy into his face while I sucked his cock. Just about the time his cock started to throb in my mouth, there was a knock at the door and in walked Buddy and Gloria. Bob introduced us, told her to strip and get us some beer from the kitchen. Without question, she stripped nude while the three of us watched. Then he had me follow her and show her where everything was.
While we walked I examined everything about the way she looked. The way she walked and talked. The way her tits and ass jiggled while she walked. How nice her pussy looked. When she bent over to get the beer, I began fingering her from behind. Then I asked if she enjoyed working at the club. I could feel her pussy start to twitch as she told me how much fun she was having. She said Buddy only let her work the hole for now but that she loved doing it. As far as she was concerned, it was the best job she ever had. I just smiled as I took the beer and followed her back to the living room.
When we got back, Bob and Buddy were sitting on the couch smiling at us. They took their beers and had me sit between them. Then they told Gloria to suck my cock. I watched as she smiled, got to her knees, pulled my pants down and started sucking. It was hard to believe, but she was almost as good at sucking cock as Cindy was. When I looked up at the TV, there was Kitty sucking cock at the hole while Jake pulled his pants down and started fucking her from behind.
I watched him fuck the hell out of me while I sucked cock. I thought about how good it felt while he was doing me like that. What a turn on it was when Bob told me that I had sucked off and been fucked by my best friend. While that was going on, Gloria was giving me a great blowjob and I blew my load in no time. I pumped my cock into her mouth and groaned about how good it felt while she faithfully gulped down my cum. When I was done, I smiled down at her while she smiled back and sucked the head of my cock.
"Good Girl.... You should be proud of yourself." I told her.
"Thanks." she said as she smiled up at me.
Then Bob had me strip nude while Buddy had Gloria get on her back so he could fuck her. I watched in fascination as he got on top of her and fucked the hell out of her while Bob and I watched. When he was done dumping his load deep inside her, she laid there with her legs spread and a big smile while cum drooled out of her pussy. Then it was Bobs turn. He got on top of her and fucked the hell out of her while telling her what a good whore she was. By the time he was done I was rock hard and on her in a heartbeat.
When I stuffed my cock into her, it was so tight and juicy, that it was hard to believe it wasn't real pussy. I instantly began to fantasize that I was her and that this is how good it felt while Jake and the guys fucked me. I dreamed about how good it felt while they fucked me. How good it made me feel to know that I was giving them pussy that was this good. It's no wonder they thought I was a girl when they were done fucking me. I looked, felt, sucked cock and had a pussy just like a real girl. Thinking about it was such a turn on, that I blew my load after only a minute or so.
"Holy Fuck! That's good pussy." I groaned as I collapsed on top of her.
Bob and Buddy laughed while Gloria giggled.
"You're not done yet ass wipe. Lick that pussy clean." Bob boomed.
I smiled and watched as cum drooled out as my cock pulled out of her pussy. Then eagerly began licking it clean. I licked and slurped at her pussy as I gulped down as much cum as I could. I could feel the tip of her cock poking out of the pee hole of her pussy and I licked and sucked on it extra hard. When she came, I slurped up and swallowed her cum too.
Bob and Buddy couldn't seem to get enough of watching us. No sooner had she started to relax then Bob grabbed my ass and started fucking me hard. Then I heard Buddy tell Gloria to get out of the way while he grabbed my ears and started fucking my mouth. He hammered his cock down my throat while Bob slapped my ass and told me what a cock loving faggot I was. Gloria gasped and giggled when she saw my cock getting hard while they abused my mouth and ass in tandem.
When they were done, Bob told me I was the biggest faggot/pussy he had ever seen. Then he told me to get changed so Kitty could suck his cock before he went home. I smiled and headed for the changing room. Buddy told Gloria to follow me and give me a hand. When we got to the changing room, I was still rock hard. Without a word, Gloria got to her knees and started sucking it furiously. While I watched her, I thought about how good she was at sucking cock and how good it must have felt for Jake and the guys when they watched Kitty suck their cocks. Again it was such a turn on for me that I blew my load in no time.
While I got changed, Gloria and I talked about how much fun we were having as girls. She told me she had been sucking cock off and on since she was 15 but hardly ever got the chance as a guy. Now that she could get dressed up and suck cock at the glory hole every night. She was in heaven.
I told her that I started sucking my own cock at 13. I told her how, until I was 18, I would jerk off until I was about to cum. Then bend over, suck the head to finish myself off, then swallow, but had never sucked anybody else's until last week. I also told her about Steve Carver. How he used to let all the guys in the neighborhood fuck him and how I always wondered why he did it. Then I told her about finding the pussy panties. Getting dressed like a girl. Bob catching me. Fucking me until I could hardly walk. Taking me to the restaurant, then the club and me going wild for cock.
We both giggled about how well things had turned out for both of us. When I was done getting changed, we looked in the mirror at the two nude girls and smiled. When we walked back into the living room, Bob and Buddy both smiled at us.
"Well it's about time! Why don't you bitches get over here and make yourselves useful?" Bob barked as he and Buddy pulled out their cocks and smiled at us.
Gloria and I smiled at each other. Got to our knees and started sucking. As soon as we were done, Buddy told Gloria to get dressed and off they went.
"Did you have fun?" Bob asked.
"I had a great time. Thank you." I giggled.
"Good Girl, I'm glad you liked it." he smiled warmly.
Then he handed me a video disc that had "Jimmy Joins The Chain Gang" written on it and went home. I smiled went to my bedroom, put in the disc and drifted off to sleep while watching Jimmy getting fucked by the prison gang.