My name is Jimmy James and this is a story of cross dressing and drunken lust.
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It was 4pm Saturday afternoon. It was cloudy, dark and the snow was coming down pretty hard. The weather reports said it was going to be -10 and a near blizzard. "Perfect" I smiled "Nobody will be out and I've got all night." I jumped up and eagerly started to dig out the stuff I wanted for the night........
As a young boy, I read an article that said men could have orgasms just from having something pumped up their ass. After some experimentation, I discovered that I could have HUGE MIND BLOWING ORGASMS without even touching my cock. That was the first step of my journey.
The second happened about a year and a half ago. My friend Bob and I had been out drinking pretty hard and went to sleep it off at his house. We went in and I sat in the living room to watch tv. Bob stumbled around mumbling to himself. Then went into his bedroom and came out a second later wrapped in a blanket. He then came out and laid on the floor between me and the tv and was soon passed out cold.
I got bored and began to look through his porn collection. I found a title I didn't recognize and quickly put it in. I was amazed to see that it was a she-male tape. As I watched, I became more and more enamoured with it. Bob tossed and turned on the floor. Eventually he rolled onto his back and laid there with no blanket. He was dressed in only a t-shirt and socks! His half hard cock laying on his belly. "Holy Shit!" I thought. As I watched the tape, I couldn't help myself, I kept switching from watching the screen to staring at his cock.
While staring at his cock and listening to the enraptured sounds from the tv. I walked over, straddled his knees and started to stroke his cock. I leaned forward and started to suck it. I thought about the best bj I ever got and did the same to him. I was soon rewarded when his cock throbbed and my mouth was filled with cum while he moaned in his sleep. I swallowed eagerly and continued to suck his cock until it went soft. The next day we got up and went about our business with Bob being none the wiser. I thought about it constantly though and it wasn't long before I was collecting everything I needed to dress as a girl.
Which brings us to tonight; It was early, nobody was going to stop by, I had all night to dress up and play with my dildos. I quickly assembled an outfit and was dressed to kill. I had on a wig, makeup, fake nails with white polish, tiny white thong, realistic fake tits in a see thru white bra, black high heeled boots, black stockings, black corset like clincher to give me a feminine figure and a slinky black dress that just barely covered my ass. I looked and felt hot! I walked around and admired the way I looked, felt and jiggled. Like always, I got turned on and got my dildos. I picked out one that was 10" long and 1"1/2 dia, it was my favorite. I pulled down my panties and generously applied lube to it and my butt hole. Sliding it in slowly, I luxuriated in the feeling of my sphincter giving way and allowing it to slide in easily. Before too long I was pounding it in hard and fast while I jumped and squealed like a bitch in heat.
That's when I heard a knock at the door! I panicked! I hid the dildo, wiped myself, pulled up my panties and straightened up my dress as fast as I could. I heard another hard knock and peeked around to look at the door. It was Bob! He was looking through the window and smiled when he saw me. "Fuck!" I thought as i ducked back "I can't leave him out there, it's too cold. He's already seen me, so I can't pretend I'm not home." I pulled back my now soft cock, rearranged my dress, gathered my courage, then reluctantly walked around the corner and to the door. When I opened it, Bob half stumbled in, covered with snow and carrying half a 12 pack. He smiled broadly. "Hi. Sorry, I didn't mean to interrupt anything. Is Jim around?" my heart was pounding a mile a minute. "No." I replied feebly "He's stuck in town and won't be back till morning." "Yeah, me too." He said nodding his head "I couldn't make it home and only made it half way up the drive." "Oh My God!" I stammered. my heart still pounding. "So you're stuck here till morning?" I was REALLY up shit creek now! "I'm afraid so. Sorry for the inconvenience."
I nervously followed Bob as he went to the kitchen and put the beer in the fridge. He pulled out two and offered me one. "My name is Bob. what's yours?" I refused "My name is Susan." I said in my best female voice. "Good to meet you Susan." he said as he eyed me up "You're not going to drink?" "No." My heart was pounding, my face was flush and I was dizzy with fear. "You can't make me drink alone." he said with a smile "Look at you! All dolled up and no place to go! At least have one with me." I smiled "Maybe I'll have a brandy and coke." "That's what Jim drinks. The brandy is up there." he said pointing. I smiled, grabbed the brady and made my drink. "You look REALLY nice Susan." Starting to calm down, I sipped my drink and giggled "Thanks."
After a few drinks, I had calmed down and Bob and I were laughing and talking. He told me repeatedly how nice I looked and how pretty I was. I was VERY flattered. So flattered in fact, that I would let him get "sneak" peeks at my panties and ass. One time, I let my dress ride up as I sat so that when I got up to get another drink my bare ass was in plain sight. I pretended to be embarrassed and pulled my dress back into place. He laughed and told me what a nice ass I had. As things went along Bob began to feel me up and grab my tits when he got a chance. He would stand close to me and caress my ass and thighs, telling me how nice i looked or smelled, then stop. I never resisted his advances and I was in fact getting turned on. I was REALLY enjoying being felt up and oogled as a woman. I was having a GREAT time! Then while sitting close together on the couch. Bob started to caress my inner thigh as we talked. I moaned softly and spread my legs. I reached over and began to massage the bulge in his pants.
Without a word, I kneeled in front of him and pulled his pants to his ankles. His hard cock slapped his belly with a resounding smack as it sprang free. For the second time in my life I was looking at another guys cock. And, just like the first, I was going to suck it till he came in my mouth. I lowered my head and slowly licked, kissed and sucked the head. I sucked more and more of it with faster and deeper strokes. The feel of his cock in my mouth was driving me wild. The smooth hard shaft, bulging veins and the fat bulbous head were making me crazy. I had to have more I thought as I pressed it hard against my throat. It popped in and slid in until my face was completely buried in his crotch. With his cock stuffed down my throat, I was thrilled when I looked up to see Bobs big smiling face beaming back at me. I sucked him hard in short quick strokes. Making sure that the head of his cock never left my throat. I held my breath for as long as I could so I could keep his cock totally immersed in my mouth for as long as possible.
When I came up for air. I pointed his cock at the ceiling and sucked the underside of cock in one continuous motion from the tip to the base and back again. His cock was hard and shinny with spit. It filled my field of vision as I watched his eyes close while he moaned and thrust his hips. I stroked it with my hand a few times and watched as a drop of fluid formed at the tip. I smiled, licked it up and started to suck his cock like a sloppy whore. I made lots of loud slurping noises as I sucked him in and out of my mouth. Soon, he put a white knuckled grip on the cushions thrust his hips and let out an "ARRRHHH" I watched as his face twisted, he shook and a steady stream of cum filled my mouth. I continued to suck just the head in short fast strokes while my mouth filled to almost overflowing. I swallowed it all and still he twitched and groaned. Cum kept pouring into my mouth as I kept up the pace. Just as my mouth was full of cum again, he relaxed and began to pant heavily. I swallowed my second mouthful.
I continued to lick and play with his cock. Looking up at him with a smile, I ask "How was that?" He caressed my cheek "That was fucking AWESOME! I had one other blowjob that I thought was killer and you just blew it out of the water! I came so hard, I thought I was going to pass out!" I just giggled and smiled with a huge sense of pride and satisfaction.
We put ourselves back together and went back to drinking and carrying on. Soon our conversation drifted back to sex. Specifically-- lap dances. He started to tease me that he was betting I could give a killer lap dance. I blushed and refused. After some coaxing and some heavy petting I agreed. I got up and swayed, jiggled and gyrated. Watching him, I was really turned on again. I climbed in his lap and pressed my tits into his face while grinding our crotches together. I could feel his already hard cock pressing back. I stepped back and pulled his pants down a bit until his cock was exposed. I then turned to face away from him, pulled up my dress and sat back down. I moved my hips back and forth and could feel his hard cock sliding between my butt cheeks. He stood me up and got behind me. His cock still pressed against my bare ass, he stripped my panties off me. "Oh" i chirped. I grabbed his cock and pressed it against my butt hole, hoping that at this late stage in the game he wouldn't find out I wasn't a girl. Still lubed from the dildo, his cock gained easy access and he groaned his approval as it was driven home. I bent over the coffee table and he fucked me HARD! Planting his seed deep inside me.
He fucked me two more times that night. The last one was the best. Standard missionary. Me on my back with my legs spread while he laid on top me and fucked me silly! Twice I came so hard I thought I was going to die! "Wow!" I thought "Who knew he had it in him?"
The next morning, I was changed and had coffee ready by the time Bob got up. "Where's Susan?" he asked as we sat down. "She left when I got here." I responded "She's something ain't she?" "Yeah she is! Wow! Hot Hot Hot! What a sex kitten!" I laughed "What did you guys do last night?" With that he retold the nights events for me. I listened intently as told me what a great blowjob he'd gotten from her, what a hot tight pussy she had, how many times he fucked her, how good it felt while cumming inside her. I of course was smiling ear to ear and was thrilled to know what good piece of ass I was. He said he loved every minute of it but RAVED about the blowjob. I was just bubbling with pride.
"So you really liked that blowjob huh?" I said smiling. "Yeah, you were really into it. It was way better than the one you gave me last year." he said slyly while sipping his coffee.