Double Played by Jimmy James
I'm Jimmy James, I had been cross dressing for a little while and enjoyed it. One day, my friend Bob and a few others hypnotized me and learned my secret.
(cd, M/M+)
=========================== Double Played
My wife and I had been married about six years. I worked hard, while she sat home. I got quite annoyed that she was so lazy and didn't feel any need to work or contribute in any way. One day while we were arguing, I told her she was the next best thing to a hooker.
"Must be nice to just spread your legs and have a someone give you clothes, food, shelter and everything else you might need." I said angrily.
She of course threatened to leave.
"What? A hooker get off the gravy train? GET REAL!!" was my response.
She packed a small bag and left that day. When I asked about when she would pick up the rest of her stuff, she got quite angry.
"I'm not a hooker!! It's all yours!! You bought it! Do whatever you want to with it!!" she said as she stormed out.
I left everything exactly as she left it.
==============1=============
That was about two years ago and we are of course, divorced. But her stuff was still there and seemingly undisturbed.
I say seemingly, because I had been dressing in her stuff since shortly after she left.
When I was 13, I had secretly dressed in my sisters clothes a few times and loved the way they fit. I was far from being a muscle bound jock. I was thin, short, I had a big ass and a smooth rounded face. So her clothes fit me way better than mine did. Quite often, I would wear her jeans because they fit better. If my mom or sister caught me in them. I would tell them I had just grabbed the first pair I saw and hadn't noticed.
I progressed to wearing more and more of her clothes. I didn't get any sexual thrill from it, but everything she had fit me perfectly and felt great. Even at the time, I had to admit that when I dressed from head to toe in her clothes, except for the short hair, I really did look like a girl
Since I was trying to define myself as a man at that age. It made me uncomfortable to know how much I looked like a girl.
So I stopped.
At 30, I still have the same build I did as a kid. When my wife moved out, all the cross dressing urges resurfaced with a vengeance. I had a house full of women's clothes, lots of spare time and I dressed in her stuff as often as possible.
This time, my cross dressing was very sexual. It was a real turn on and I worked quite hard to be good at it. I found a way to pull my cock and balls around so if I had tight panties on, it looked like I had a nice camel toe. I had bought realistic glue on breast forms, grown my hair long. It all looked and felt good, but my ass is what made me convincing as a girl. It looked great peeking out from under my skirt. It was the first time in my life, my big ass had come in handy.
I would play with my wife's dildos and would picture myself as a woman as I sucked on, deep throated and fucked myself silly with them. It was a shame that I couldn't make them cum. I always wondered what it would be like to have them cum inside me or swallow a big mouthful.
One of my favorite things to do was to dress in sexy lingerie, stick a vibrator up my ass and do housework.
The vibrator was one of those egg shaped remote control things. I wasn't sure about it when I bought it, but once I tried it. I thought it was the best thing ever invented.
It was a simple cylinder, rounded on both ends, 2 inches across, 6 inches long and each end vibrated separately. It was long enough and fat enough that when I stuffed the whole thing in, it was a real snug fit.
The remote was attached by a thin wire about two feet long. It had a range of speeds and settings for each end. Random was my favorite. While I did the house work, it would go on, off, speed up, slow down whenever it felt like it.
I would dress up in whatever lingerie I chose. Stick the vibrator in. Pull my cock back. Clip the remote to the side of my panties. Set it on random and do my housework. Except for the wire sticking out of the back of my panties and the remote. You couldn't tell it was in there.
It was great! It felt great every time it went off too!
I would be vacuuming or doing the dishes or something when it would go off and it drove me wild every time. The best part was, I could have really intense orgasms too. Lots of them!
When I discovered that, all my dildos got extra duty. My cock didn't get hard and only a few drops of cum came out, but it felt great. Plus: They weren't as satisfying as when I stroked my cock, but there were lots of them. It was an excellent trade off.
============2==============
Since I was divorced, I had more free space, so 5 of my friends would come to my house Sunday mornings. We would hang out, pack our coolers and drink a few beers before heading to the golf course.
One day just before we were about to leave, Bob was talking about how he had been studying hypnotism. Everybody thought that it was cool. I was the only person that thought it was a hoax. No different than any other magic trick.
When he said he could hypnotize me, I just scoffed. He challenged me to try it. I of course agreed. He stood me in the middle of the room. Went through some relaxation exercises. The next thing you know, I was out like a light.
Everyone thought I was pulling their leg, so Bob had me do a bunch of silly things which I did without question. They still weren't convinced so Bob thought for a minute. Then he smiled at everybody.
"Drop your pants." he said loudly.
I of course did it without question. Everyone, including Bob gasped when I did. There was no question about weather I was really hypnotized now. My legs were shaved and I was wearing a tight pair of white cotton bikini panties that were pulled deep into my camel toe.
"Why are you wearing those panties?" Bob asked in shock.
"Because they make my camel toe look so real." I told him flatly.
"Wow! They sure do!" Bob said absently.
I smiled while everyone stared at it.
"Do you dress like this often? Tell me all about it." he said as he smiled at me.
"All the time" I said.
I then proceeded to tell them all about dressing up as a kid and what I thought of it. I told them I had been dressing up like a woman since my wife left. That I liked to dress in lingerie when I did house work. How convincing I was and how sexy I felt doing it. The guys just listened and stared at my camel toe.
"What do you think guys? Wanna see what Jimmy looks like as a girl?" he asked with a smile.
The answer was a resounding "YES!!" they were all for it.
Bob chuckled "You heard 'em...... Go put on something sexy. Like you're getting ready to do some housework."
I pulled up my pants, and they followed me to the bathroom. They watched dumbfounded as I stripped nude and rinsed out my ass with water real good They followed me to my bedroom and watched as I picked out some lingerie and collected the stuff I would need.
I returned to the bathroom. Glued on my tits. Put on white thigh high stockings. White bustier that left my tits exposed. White five inch heels. Did my makeup and nails. I had my hair in a braid and when I shook it lose, I had long curly red hair cascading over my bare shoulders. The last thing I did was to put on my panties and the guys were shocked when they saw what happened while I did that.
They had only asked about dressing up. They didn't know anything about the vibrator. I pulled my white lace thong half way up. Dug my vibrator out of the bag. Put a little lube on it then stuffed it deep inside my ass. I pulled my cock back. Finished pulling up my panties. Arranged my cock and balls so I had a nice camel toe on display. Clipped the remote to the side of my panties and I was done.
Nobody could believe what they had just seen. Bob looked at everybody in shocked disbelief.
"Anybody want to see her do housework?" he asked.
Again, the answer was a resounding "YES!!"
Bob stood in front of me and issued instructions. "When I snap my fingers, you'll be awake and refreshed. You will think you're alone and ready to do some housework. You won't notice us and will do like you do on any other day. But from now on, when I say "EEM KUF" you will be back in this hypnotic state. Understand?"
"Yes" I nodded.
He smiled at everyone and snapped his fingers.
==============3=============
I turned the vibrators on high and giggled at the sensation. You could clearly hear the humming noise. I smiled at myself in the mirror while I watched my belly flutter with the vibrations just above my pussy. I loved doing housework like this.
I left the vibrators on high and went to the laundry room. I had a big smile as I did the laundry and enjoyed the way I looked and felt. Mostly I enjoyed the way my vibrator felt going wild in my ass. No sooner had I separated the clothes and put the first load in, than I came.
"Oh god! Oh Fuck! Uh Uh Uh" I squealed as I danced around and held onto the wash machine for support.
I shuddered and shook through my orgasm, desperately clinging to the wash machine. As I regained my senses, I smiled real big and put the remote on random. Then I began vacuuming the house. Every time the vibrator switched on, I squealed and danced around because it felt so good. Before I was done, I came. I put the vacuum away, did some dishes, came again. By the time I came for the fourth time, Bob couldn't take any more.
"EEM KUFF" he said loudly and I was out.
"Have you ever fantasized about sucking five cocks then pulling a train?" he asked while smiling at the guys.
"All the time" I responded.
"When I snap my fingers, you're going to walk back into your room then back to the living room. When you walk back out of your room, you will be awake and refreshed. You will think that we stopped by to play golf, but you hypnotized us instead. Now you're going to live out your fantasy. When we're done. You will send us home thinking that we played golf all day with no memory of what we really did. You will spend the rest of the day doing whatever you want. In the morning, you won't remember that I hypnotized you or that I know hypnotism. You will think that we spent the day golfing and that hypnotizing us was a sex dream. Understand?" he asked.
"Yes" I replied.
Bob smiled at everybody and snapped his fingers again. I turned and walked to my room while they stood in the living room with their eyes closed.
When I stepped out of my room, I had a huge smile and couldn't believe my luck. I curled my hips as I felt my vibrator going off inside me. I was finally going to be able to play with a real cock while dressed in lingerie. Not just one, I had five cocks to play with all afternoon. I had hypnotized five of my friends and now I was going to live out some of my deepest darkest fantasies.
When I walked back into the living room, I looked at my friends and smiled again at what was about to happen.
"Open your eyes, strip naked and form a line right here." I said in a commanding voice.
While they stripped, I could see that all of them were hard and I couldn't help but to smile. I had five hard cocks in a row, waiting for me to take care of them. I walked down the line with a smile as I did an inspection. I stroked all their cocks to make sure they were good and hard. I loved the way their stiff cocks felt in my hand.
Then I went back to Bob at the beginning of the line. I gave him a big hug and watched as my naked tits mashed against his hairy chest. I listened to him moan as I ground my belly against his hard cock. I turned around, backed up to him and playfully swung my ass back and forth.
Having a stiff cock brushing against the smooth round globes of my ass was driving me wild with excitement. When my vibrator went off, I just about freaked out and groaned loudly. I stroked his cock a few times then did the same to the next guy. I moved down the line and did the same to all the guys. By the time I was done, I was so turned on, I could hardly stand it. I had no idea playing with a real cock would feel so good or be so much fun.
I knelt in front of Bob and stroked his cock only inches from my face. I could see that his cock was dripping pre cum and eagerly licked it up. I smiled at how good it tasted and sucked his cock in until my face was pressed against his belly. I heard him grunt as it plunged down my throat. His cock tasted and felt so good in my mouth, I couldn't get enough. I sucked the whole length of his cock slow and easy to soak in the sensation.
It was incredible!! If this was what it was like for women, I didn't understand why they didn't pay to suck our dicks. The best part was when his balls exploded into my mouth. His cock throbbed forcefully. My mouth was flooded with cum and I swallowed as fast as he could feed it to me. It was the most incredible feeling and it was over far too soon for my tastes.
The next guy I sucked off the same way only faster. When he got off, I swallowed for him and moved to the next guy. Every time I moved to the next guy, I sucked his cock harder and faster. Each guy seemed to get off faster than the last. When I got to the last guy in line, I put his hands on the sides of my head and looked up at him.
"I want you to fuck my mouth like it was a pussy. Then I want you to cum as deep in my throat as you can get." I told him.
I wasn't sure how things were gonna go, but I wasn't disappointed. He grabbed the back of my head and throat fucked me hard. When he came he mashed my face against his belly and came hard while grunting and groaning. If I live to be a million, I will never forget the way it felt to have a guy cum in my mouth or throat for the first time. It was baffling to think that there were women out there who didn't want to do this.
Having a fat, stiff cock going off in my mouth was the thrill of a lifetime. The vibrator going off randomly in my ass made it an even more unforgettable experience. I had three orgasms before I was done sucking off all five of them. It was so much fun, I couldn't wait to see what it was like to have them fuck me.
=============4=============
"Everybody go to the kitchen. Grab a chair and meet me in my bedroom." I told them.
I went to my bedroom. Took off my panties. Pulled out the vibrator and laid on the bed. I watched with a smile as they walked in with their chairs Four of the five of them were already hard again.
"Sit in a line right over there." I told them pointing to the foot of the bed.
They set up their chairs and stroked their cocks with a smile.
"No stroking! I always wanted to get fucked missionary style while pulling a train. As soon as one guy gets off, I want to feel the next guy on top of me as quick as possible. I want you to fuck me hard, cum inside me and make room for the next guy. Understood?" I asked.
They all smiled and said yes. I spread my legs wide while smiling at Bob.
"The train is now ready for boarding at the rear of the station. Please present your boarding pass, take your seat and enjoy the ride." I said with a smile as Bob climbed on top of me.
I heard him groan with pleasure as he stuffed himself balls deep into my cock hungry ass.
"God that feels good in there. How is it for you?" I asked expectantly.
"Holy Fuck This Feels Good!" He assured me.
I giggled "Tell them about it."
He looked over at them "Wait till you try this. She's an awesome piece of ass!"
They just smiled.
"You guys are my cheering section. If you see something you like. Let's hear it. And don't be afraid to tell me if it feels good." I said waving my hand and patting Bob on the back.
The guys erupted into boisterous cheers while making choo choo noises. The train is now leaving the station. I heard one of the guys say as Bob began to pound his cock into me hard and fast.
In no time, I was jumping and squealing about how much I loved cock. Bob was groaning about what a good fuck I was. The guys were cheering about what a hot ass I had. How hot it was to watch me suck cock and get fucked like a whore.
After about ten minutes, I erupted into a mind blowing orgasm. Everybody watched and cheered as I flopped around like a fish out of water while screaming for Bob to fuck me harder.
All the action must have set Bob off, because he pumped deep inside me and I felt his cock start to throb. He grunted in my ear about how good it felt to cum inside me. I thrust my hips up, smiled real big and told him I thought it felt great. It was way better than good. It was great and he could do me like this any time he was hard.
Just like I had instructed, the instant he was done, he climbed off and the next guy took his place. We smiled at each other as he forced his cock in.
"Enjoy your ride" I giggled.
"I sure will. You're a hot piece of ass!" he smiled.
The guys heard that and began cheering immediately. Bob told them what a good fuck I was and that it would be the best ride of their lives. All four began to make the chug a chug a chug a..... choo choo noises in unison I couldn't help but to laugh and join in. When they got to the choo choo part I put my hands and feet as high as they could go. Instead of saying choo choo though, I would squeal Fuuuuck Meeee!!
Everybody thought that was great and we all busted out laughing. Bob and the others continued with the Choo Choo sounds while the guy on top of me fucked the living shit out of me. I loved it too! He was really good!! I squealed and groaned the whole time. I even came again. That of course got a huge response from the cheering section.
He got off inside me and made room for the next guy, just like they all did. By the time the five of them were done with me, I had cum seven times I was exhausted.
"For the next hour, you can do what every you want to me." I said waving my hand.
They talked about it for a little while, got their boarding passes straightened out and rode the train again.
When they were done, I had them put their chairs away and get dressed. I told them that the instant they started their car, they would be awake and refreshed. They would forget what happened and think they were on the way home after a hard day of golf. I had a huge smile as I watched them jump in their cars and drive off.
I had such an elated feeling. I had sucked off my five best friends while the others watched. Then I had pulled a train for them twice and they would never know. I began to stroke my cock while I thought about it. It was such a turn on, my cum flew half way across the room.
I giggled, thought about how my wife had always bitched about sleeping in the wet spot. I jumped back in bed and rolled around in the wet spot until my whole mid section was covered with a thick coat of cum.
I spent the rest of the night dressed as a girl while fucking myself hard with my dildos.
=============5==============
When I got up in the morning, my ass and belly were covered with something sticky. But I didn't care because I had such a great day yesterday. I had spent all afternoon playing golf. I spent all night fucking myself with my dildos. To top it off, I had a really erotic sex dream.
My friends had stopped by for golf, but I hypnotized them instead. Then I sucked them all off while the others watched. I pulled a train for them twice while they cheered about what a hot piece of ass I was. How sexy it was to watch me suck cock and be fucked like a whore.
It had to be the most vivid and erotic sex dream I ever had.