Becoming Missy

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It all started back in 1973 in Seattle, Washington.
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It all started back in 1973 in Seattle, Washington. I was 21, living on the south side with a couple of buddies while we were all stationed at area military bases. One Friday night we had a party at our apt. I was standing outside by my car smoking a joint when this guy pulls up in his pick-up. "Hey, how's it hangin?" he asked

"Long and loose." I replied trying to be funny.

"I'm Bobby." he said as we began making small talk. I found out he lived in Portland but was staying just up the street for the weekend. "Just how long is it?" he grinned

"Well, it gets the job done," I answered. "I hope you're not a narc I said as I passed the joint to him.

"Not hardly." he laughed. "So tell me, do you like blow jobs?" he asked.

"Sure, doesn't everybody." I replied thinking that it was a strange question to ask.

"That's good, because I want to suck your cock." he said dropping his eyes to the front of my pants. I stood there in shock I couldn't believe what he had just said. "I'll give ya 20 bucks if you let me suck your cock." he added.

I could feel the blood rushing to my cock as I heard myself saying "20 bucks to suck my cock?... you got a deal."

Obviously this had to be done carefully as not to arouse the suspicions of the others at the party, most of which were military, and many I'm sure were fanatically homophobic. We went inside and with an excuse of a drug deal to my roommates, went to my bedroom. Once in my bedroom Bobby locked the door and began unfastening my pants. Oh damn too late now I thought as I remembered the blue nylon panties I was wearing.

"Nice panties sweetie." he teased as he took my pants off and started rubbing my cock thru my panties. "Take your shirt off," he whispered as he pulled off his shirt and pants and then pushed me down on the bed. "You got a beautiful cock," he whispered as he slid my panties down and began to lick my cock. He lay down beside me with his cock just inches from my face. As he kissed and licked my balls I stared at his circumcised 6" hard cock, "suck it," he pleaded he pushed his cock to my lips.

"Nooooo....... I never have ....I don't suck cock," I whispered moving my head to avoid his cock. I could feel the wetness of his precum on my lips as he tried to push it into my mouth. Giving up, he took me into his mouth and began to work up and down my shaft giving me the most fantastic blowjob I had ever gotten and the first I had ever gotten from a man. I was staring at his hard cock just inches from my mouth thinking about how it felt against my lips, but before temptation could overwhelm me I was ready to cum. "Oh Bobby....I'm gonna cum," I breathed causing him to suck me all the harder and faster. "Oh my god yes, take it," I was moaning loudly as I as I dumped my semen in his hot mouth." You're a fantastic cocksucker," I gasp as he drained the last few drops of cum from my cock.

Before swallowing he opened his mouth showing me my cum then swallowed it down it down followed with a long belch, "Its not bad manners just good cum." he quipped.

Hearing the noise attracted my roommate's attention, knocking on the door he asked "are you ok?"

"Yeah, we'll be out in a minute" I answered as Bobby and I jumped up and quickly got dressed. "Did you like it," Bobby asked grinning coyly as he unlocked the door.

"Of course I did silly," I replied as Bobby gave me $20 as if to pay for the drugs that my roommates thought we had just done.

"If you liked that just wait until I take your panties down and fuck you," he said as we walked out to his truck and he got in.

"My roommates are going to Canada tomorrow, I'm supposed to go, but I'll stay here if you're going to come back." I cooed. I was hoping he would as I reached thru the window and squeezed his cock. Licking my lips I could taste the faint flavor of his precum as I thought about how it made me feel when his cock touched my lips.

"It's a date I'll be back tomorrow afternoon" he promised.

The next morning my roommates departed for Canada. I had been fantasizing all night about what I wanted to do, now it was time to act. My job on the base gave access to women's locker room, that's where I had gotten my blue panties and a few other miscellaneous pieces of lingerie, tops and a couple of skirts that had been inadvertently left behind by the owners. I went to Pik'n'Pak and bought some pantyhose and makeup, then back home to get dressed for my big date. After bathing and completely shaving my body I put on a white nylon bra stuffing the A cup with tissue, then white nylon panties, sheer nude pantyhose with a black satin miniskirt, a white shell top, a pair of black heels that I had gotten from the salvation army completed my outfit. With a little makeup, eye shadow and lipstick I thought I was passable even with my short hair.

I was so excited I could hardly stand the wait until I would see Bobby again. Just after noon I heard a knock on the door, looking out the window I saw Bobby's pickup. My heart was pounding as I answered the door. He came in and as he checked me out he asked "who's the fox" playing along with my little charade.

"I'm Missy" I giggled.

I felt so feminine as he took me into his arms and kissed me, his tongue entering my mouth. As our tongues explored each others mouths his hands found my ass, Bobby was treating me just like a girl, I was so excited I could feel a wet spot forming in my panties.

"Come on Missy let's go for a ride," he suggested.

"I can't go out dressed like this Bobby," I replied "someone might realize I'm not really a girl." I added.

"We'll just drive around baby, no one will notice, anyway who cares, nobody knows us." he coaxed. I agreed to go, as I put my makeup and ID into a purse.

Walking to the truck I could feel the breeze on my nylon covered legs, god this is so exciting I thought as we got into the truck. "Slide on over next to me Missy." Bobby said. As I slid over next to him my skirt rode up exposing my panties "you got great legs baby," he said he sliding his hand between my thighs.

"Thank you Bobby," I purred putting my hand on his cock, I began to knead it as he drove. It was making me so hot, the harder his cock got the wetter my panties got.

I felt like I was in a dream out in public dressed, Bobby caressing my nylon covered thighs, before I knew it I had unzipped his pants and exposed his cock. I played with his cock wantonly as I watched a drop of semen form on the tip, I lowered my head and licked it from his cock slit, his cock head felt soft and velvety and his cum tasted wonderful. I had started to lick up and down the shaft when I felt Bobby's hand on the back of my head "suck it Missy...... you know you want to.....don't you baby?" he softly said.

"Yes Bobby I want to suck your cock," I cooed as we pulled on to the freeway.

"Missy you're so hot.... do it for me baby.....pleaseeee," he begged. I was shaking as I parted my lips letting his drooling cock slide into my mouth. "Damn your mouth is so hot Missy " he panted as I began to slowly work up and down his shaft swirling my tongue around his cock head then taking it into my throat. "Oh my god Missy, faster baby faster, suck my cock" I could hear the urgency in his voice. I could feel his cock growing larger and I began sucking as fast as I could "I'm gonna cum baby" he yelled. I felt his cock spasm as he held my head down filling my mouth with his sperm. I was swallowing it as fast as I could when I felt my own cock jerk and fill my panties with cum. I pulled back as he let go of my head allowing his cock to slip out of my mouth and blast my face with a string of cum, but I quickly got him back into my mouth and drained his cock then licked it clean. With cum running down my chin as I raised my head I heard an air horn blast, looking up thru the window to my horror I saw a semi driver giving me the thumbs up and grinning ear to ear.

"Bobby!!" I screamed "how long has he been watching us." I was wiping the cum from my face and licking my fingers when I heard another horn and saw a semi pacing us on the other side, the driver nodding at me."Bobby!!!"I screamed again.

"They saw the whole thing baby," he howled. "You put on one hell of a show, those guys will be hard for a week Missy." he said laughing.

"Speed up and get away from them.....and find me a bathroom I need to clean up" I snapped crossly. Bobby pulled into a rest area down the road a couple of miles and grabbing my purse I stomped off to the ladies room to freshen up. After cleaning my panties and washing my face I emerged from the bathroom with fresh makeup and lipstick, my anger gone after all I had just sucked my first cock and I loved it.

"Hi there little lady" I heard the strange voice say I turned and came face to face with a very large man. He was one of the truck drivers that watched me suck Bobby's cock. He was loitering in the vending area obviously waiting for me.

"Hello" I said politely as I started to walk toward the door.

"That was quite a show you put on back there, left my cock hard as Chinese arithmetic," he said stepping in between me and the door "I don't suppose you could help me out here" he asked rubbing the front of his pants.

"No that's definitely out of the question, my boyfriend is waiting right outside." I said tersely.

"Too bad he can't see you from where he's parked, sweetheart" he growled as he shoved me into the men's room, "we can do this nice or........" he threatened as a smaller man, I recognized as the other driver stepped out of a stall with his zipper down and his cock out. I knew what he meant.

"Pleaseee I'll do what you want just don't hurt me" I sobbed as the smaller man grabbed my arm.

"See, I told you she wanted to suck our cocks that's why she stopped here, ain't that right sweetheart." he sneered.

"Uh huh" I sobbed dropping to my knees, not wanting to get hurt or worse I began to lick his cock, swirling my tongue around the head a few times then engulfing his entire cock. Suddenly he grabbed my head and face fucked me briefly before unloading his trucker spunk down my throat.

"Damn Sam she's one hell of a cocksucker as he pulled his cock from my mouth and wiped it on my face before stuffing it back into his pants.

"Hurry up I don't have all day my boyfriend's waiting." I said still on my knees. As the other driver stepped in front of me I unzipped his pants, and freeing his cock popped it into my mouth.

"Oh yeah that's good pretty lady" he moaned as I went to work on his cock. It didn't take long before he warned me "I'm gonna cum honey" then pumped a torrent of man juice down my throat. He must of been saving it up for months I thought to myself as I struggled to swallow it all. After I milked the last drop of cum from him he quickly put himself away. "Thanks a lot honey" he snickered as walked out the door, the other driver was already long gone. As I got up and went to the sink to freshen up again and put more lipstick on I found two $100 bills.

"What took you so long" Bobby asked impatiently as he started the truck and pulled into traffic.

"A girl has certain things to take care of you know." I said sweetly in his ear. I'm sure he knew the truckers had cornered me in the bathroom, maybe even set it up I thought as reached into his crotch and began massaging his cock. "Why don't we go back to my place and you can show me what you can really do with this" I purred as I pulled his cock into the open. I stroked his cock a few times then engulfed it and began to piston it into my mouth. Oh god I thought to myself three cocks and I had developed an insatiable hunger for cum.

"Oh god yes Missy... suck my cock baby" Bobby moaned as I worked his cock in and out of my mouth swirling my tongue around his glans. "I'm not gonna last very long baby" he said as he started to fuck his cock into my mouth.

Taking him out of my mouth "that's right baby, feed Missy" I purred softly then started working on his cock again this time stroking him with my hand as I sucked his rampant cock coaxing his turgid balls to yield their cache of sperm.

I felt his cock swell and as I squeezed his balls he erupted "oh my god Missy swallow my load." he cried. I feasted on shot after shot of his copious spunk, then licked him clean after nursing the last drop of sperm from his deflating cock

"Take a bow baby," Bobby laughed, as I sat up in the seat. God, we had left the freeway and were sitting at a traffic light and I had just given another public cocksucking exhibition to several pedestrians standing on the corner.

"Bobby you bastard," I shrieked with false outrage. Actually I was quite proud of myself lewdly licking the remnants of sperm from my lips and grinning coquettishly as a couple of the guys that had watched me suck Bobby's cock nodded and grabbed themselves.

We rode quietly and uneventfully the rest of the way to my place. Stepping inside Bobby kissed me and breathed, "Missy I want to fuck you so bad I can't wait any longer" as he picked me up and carried me to my bed. After stripping his clothes off he pushed my skirt up then ripping my pantyhose pushed my panties to the side and began to tongue my asspussy.

"Pleaseeee.......oh god, eat my asspussy Bobby........oh don't stop baby ..you're gonna make me cum" I screamed filling my panties with cum as he tongue fucked my ass. "Fuck me.....fuck me now Bobby." I demanded. I felt his tongue leave my asspussy, replaced by his cock "give it to me baby, fuck me with your big cock" I pleaded as I felt him enter me. His cock head slipped past my sphincter inflicting incredible pain on my virgin ass, causing me to scream "stop it Bobby, god it hurts, your ripping me apart."

"It'll be ok Missy" he soothed as he held very still for a few minutes then as the pain eased a bit he began to push into my mangina again slowly until I felt his balls against my ass, oh yes, he was in all the way!!!

"I'm gonna fuck you good Missy." he whispered. He began to fuck me slowly at first then building speed until he was pounding his cock into me as hard and fast as he could. "Your asspussy's so tight baby it's gonna make me cum ......... I'm gonna fill you full of cum." he moaned.

"Ooooh yeah Bobby fuck me I want to feel you cum,........pleaseeeee cum in my asspussy." I begged.

"Oh baby,,,, oh my god I'm cumming... take it bitch" he yelled as I felt him pumping his sperm into my mangina.

I couldn't believe how good it felt as his cum filled my mangina, it was so hot and there was so much of it as I purred "ooh Bobby fill my twat with your hot cum." Bobby continued to fuck his cock in and out of my sodden mangina "oooooh baby don't stop..... I'm gonna cum" I screamed. As I milked his cock with my asspussy my cock spewed it's load of sissy cream into my panties. "My god, Bobby that was sooo good" I cooed, as he kissed me then rolled off me. I moved down between his legs and cleaned the remnants of our lust from his cock and balls as Bobby fell into an exhausted sleep. I nursed on his flaccid cock until I fell asleep.

When we awoke it was morning and I knew my roommates would be home in a couple of hours. Bobby told me over breakfast that he had to return to Portland to work and if I was ever in town to look him up at the Circus Bar .

I sucked his cock again on my knees in the shower "You are a fantastic cocksucker" Bobby moaned as I brought him off and swallowed his yummy load of hot cum.

When I stood up Bobby bent me forward against the wall, soaped my asspussy and entered me as I begged "fuck me good baby." Bobby fucked me for a long time, then just as the hot water began to run out I felt his cock swell then jerk and his hot sperm flooded my mangina

"Ooh Bobby....cum in my pussy knock me up" I purred as I milked every drop of sperm I could from his bloated balls. After we finished our shower, he got dressed, kissed me was gone.

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AnonymousAnonymousabout 9 years ago
please continue

This was a great first story of how you became Missy. Please continue. I can't wait to read about your sexual adventures as a hot sissy CD (just like me !!! )

AnonymousAnonymousover 11 years ago
looking

I couldnt put it off any longer,i wanted to dress and get picked up and experience what a women feels.I put on pantyhose,sheer white panties,a dress and wig and went to a local club.I am 36,passable ,i sat down to have a drink.After awhile i noticed an older guy looking at me,i looked back,smiled,my stomach in knots,he walked over,may i sit with you,i smiled,yes.We talked for awhile,a few more drinks,then he said,look the coffee is not good here,would you like to come to my place.Thankyou that would be nice,he stood and he guided me out.Drove a short distance to a nice flat,he opened the door,please sit,i will make the coffee,i went to his bathroom,made sure i was well lubed,walked back,drank,he sat next to me,his hand rested on my knee,i waited,it moved a little further,my cock started to get hard,did he know,i said i have to tell you something,he said,dont worry,i know,his hand resting on my pantyhosed hard cock.My legs opened,his finger slid under my balls,caressing my pantyhosed hole.He stood,lifting me,to the bedroom,on my knees,my dress lifted, pantyhose and panties down,his cock pressing at my hole,it wouldnt go in.I said first time,he moved,lay on the bed,here,i straddled him,he positioned his cock and i sat slowly down until my hole opened and gradually his cock slid up into me.He was gentle,as i gradually got used to his cock,i began to move more quickly up and down,my cock sticking straight out as i ground down on him,felt him get bigger and my cock shot long ropes of cumm into the air causing him to hold my hips and fill me with his.I didnt want him to stop,i just kept pushing down until we could take no more and he slid out.First time,great

heellovr69heellovr69over 12 years ago
HOT as fuck!!!

Hon, that made my CD clitty hard in my G-string panties. Sure wish I were you getting my asspussy filled with man sauce.

toni49toni49over 12 years ago

wow what a wounderfull story so hot love to been in your shoes

JentvcdJentvcdover 12 years ago
Really a Great Story

Enjoyed this a lot wishes this would happen to me sometime.

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