Michael's Prom Night (A Chrissie Conway Story

Micheal’s Prom Night (A Chrissie Conway Story)


Kelly and I are home for a few days and were staying at Kellys' mom’s house as usual. All week long all her b*****r Michael can ramble
on and on about is the senior prom coming up this Friday night. He and
Two of his buddies decided to pool their money and talked Kelly into renting them a Cadillac for prom.
When any two of them are together all then talk about is how they are
finally going to laid on Friday. They been waiting the entire school year for prom weekend because the popular myth is that even girls who don’t “do it”, will make an exception on prom night. Now this little gem of high school legend has been around since way before even Kelly and I graduated. As anyone with half a brain knows if a girl is going to do it she doesn’t need prom night to get her cherry popped.
The guys plans involve getting a hold of some alcohol and few joints and somehow magically they will be able to break down any inhibitions their dates might be harboring. By their convoluted way of thinking they forked out a lot of money for tuxedos, corsages, dinner and of course the Cadillac so naturally once they’ve applied the alcohol and pot their dates should be more than willing to put out.
The more I hear them talk about the impending prom night bacchanalia the more concerned I become that they won’t last until Friday night and will wear themselves out jerking off every time they get to thinking about what they are anticipating.
When Wednesday rolls around Michael comes home from school and proceeds to toss his book satchel across the room. Kelly asks him what wrong to which he replies “I’m fucked. That’s all.”
“What the hell is wrong this time?” Kelly asked him.
“Well only that Carrie has mono and can’t go to the prom! That’s all!!” he answered.
“Wow that’s fucked up isn’t it?” she said. “Too late to find another date eh?”
“Ya think?” he said sarcastically.
“Maybe you find a chick who doesn’t have date. She’d probably be ugly as sin but at this point you can’t be too picky.” Kelly said with smile.
Kelly's mom, Kelly and I all laughed in unison.
“Very fucking funny.” Michael said “I hope you’re all enjoying this?”
Them Kelly said “Seriously their has to be someone you can take. Then at least you can go and you won’t have wasted the money.”
“Yeah sure, maybe you could find me someone?” Michael said.
There was a long pause and for a while the room was silent as the
three of us stared at each other trying our best to commiserate with Michael and his problem. Then the two women, almost as if it had been rehearsed, shouted out together “CHRISSIE!!”
“Whoa there!” I said with laugh “Maybe someone should ask Chrissie first?”
“Come on Chrissie. Do the k** a favor.” Kelly said.
“How come no one is asking me if I’d want to go to the prom with Chrissie?” Michael asks.
“Why wouldn’t you want to?” Kelly asked “I doubt you ever dated a girl better looking than Chrissie?”
“That’s not the point.” He replied “You forget I’ve known Chrissie since way back when she was still called Chris.”
“Yeah and once she became “Chrissie” your little pecker got stiff every time you saw here.” Kelly said.
The three of us laughed at Micheal’s sudden embarrassment. He started to walk away but then turned and said “OK I’ll take Chrissie if she is willing to go?”
“What do you say Chrissie?” Kelly asked “You’ll do it. Right?”
I sat there thinking about it and then thought, what the hell, why not?
“I just thought of something genius Kell. Have you considered where we’re going to find a suitable prom dress at this late date?” I asked.
“Leave that to me Chrissie. I’ll come up with something.” She answered.
Kelly immediately began feverishly making phone calls to every old girlfriend in town in search of a dress. Eventually she talked to an old friend whose s****r graduated last year and still had her dress. Only a year old it should still be in style and she made arrangements to pick it up at the girl’s house. The s****r was a petite little thing like me so hopefully we wouldn’t have to alter the dress any.
The night of the prom I was determined to continue the illusion that I was Micheal’s high school girlfriend. I decided I would dress a little provocatively but not like a slut. I chose a rather demur pair of pink panties with just a bit of lace trim and a pink strapless pushup style bra. I am normally a stockings and garter belt girl when I dress up but I decided on this occasion pantyhose would be a better choice. I borrowed some cheap pearls from Kellys' mom and Kelly found me a pair powder blue pumps. The shoes would compliment the dress and would also be suitable for dancing. I arranged to have my hair styled at a local shop Friday afternoon and also had my nails professionally manicured. The prom dress itself was on off one shoulder style which hung to just above my knee. The pushup bra shoved enough of my breasts up out of the top of the dress that I quite certain it would create a bit of interest.
Micheal’s friend Terry showed up at 6:45 in the rented Cadillac and the two of them left to round up their friend Jeff. When they returned Jeff and Terry were elegantly attired in their rental tuxedos and elected to wait out on the deck while Michael changed into his tux. I was doing some last minute primping while Michael was changing.
Once we were dressed and ready Michael and I joined the others on the deck.
“WHOA!!!!” Terry exclaimed as I stepped out on to the deck. “Mikey,
this is your stand-in date?”
“This is Chrissie.” Michael answered “What do you think for a last minute replacement?”
“Damn! Mike, she’s a lot hotter and Carrie.” Jeff said. “I mean I don’t mean to be dissing Carrie or anything but…but……dude, this chick is Hot!”
Michael turns toward me and winked as if he were finally pronouncing his approval of this arrangement.
We all walked toward the Cadillac and Terry and Jeff got into the front seat while Michael and I got into the rear seat. There was very little chit chat as we headed off to pick up Terry’s date. Michael asked Terry if he’d rolled the joints. He assured him that he had done it. Jeff than informed
us all that he had a bottle Jack Daniels under the seat.
When Terry’s date joined us we decided that the guys would ride up front the girls would be in the backseat. Jeff’s date was the last one to get picked up and once her parents were done taking pictures of her and Jeff and then all six of us we continued on to the prom.
I was feeling kind of weird riding in the backseat with the two girls and I asked Terry if we could light up one of the joints.
“Why not.” he said “Let the party begin.”
I wound up taking several hits off the joint and handing back to the guys up front after the other two girls declined to smoke it. I thought this could be a
long evening if these two girls turned out to be super straight. It didn’t look to good for the big orgy the guys were hoping for.
I danced several dances with Michael and it was much like dancing with a relative at a wedding. I told him several times if he wanted to mingle around and dance with some of the other girls I wouldn’t blame him. The way all the guys were staring at me I figured it wouldn’t be to hard to get some of them to ask me to dance. I did dance with several other guys that night including both Terry and Jeff. Virtually every guy I danced with made every attempt possible make sure his body was pressed as close to mine as he dared. Their hands frequently found a way a way to make casual contact with my ass.
When ever any one asked Michael who I was and where I came from, he would tell them I was college friend of his s****r’s.
The dancing ended about 10:00 PM and a catered supper was provided afterwards. Following the supper we left the Elks Lodge where the prom was being held and once we all back in the Cadillac Terry pointed the car in the direction of Riverside Park which had always been the local make out spot. I wasn’t sure how six of us were supposed to comfortably make out with 3 guys in the front and 3 girls in the back? When we got to the park
I whispered to Michael that he and I would leave the car since I doubted that he intended to make out with me and that way the other two couples would have more privacy. I told him to get another joint from Terry and to grab the bottle of Jack Daniels.
We headed over toward a stand of trees and sat a picnic table passing the bottle back and forth. We’d killed about half the bottle when Michael lit up the joint. We split the joint and between the bourbon and the weed we were feeling giddy. Michael thanked me for doing this for him and I told him that turned out to be kind of fun. I asked him if anybody asked him any weird questions about me.
“I wasn’t going to bring it up and I hope you don’t get mad at me Chrissie?” he said.
“Hmmmmm?? I wonder where this is going?” I asked.
“Well, in the Mens room after dinner Jeff said that he thought he knew you from somewhere?” Michael said and then paused….
“ So what did you tell him?” I asked.
“I told him that you were been my s****r’s friend since you were both k**s.” he said.
“Yeah so what’s wrong with that? That’s true.” I replied.
“I know but then I told him that you weren’t always Chrissie and that used to be “Chris”. He said.
“Wow. What possessed you to tell him that?” I asked.
“I don’t know it kind of just came out.” he said. “I’m sorry Chrissie.”
“I guess it’s no big deal if he knows.” I replied.
“You know Chrissie, he probably told Terry.” Michael said.
“Oh well.” I said “It is what it is.”
When we were good and d***k and stoned on top of that we saw the headlights in the Cadillac flashing toward us. We staggered back toward
the car.
When we got near the car I noticed that the girls were both in the backseat and Terry and Jeff were walking toward us. I figured the three of them wanted to discuss something so I continued toward the Caddy. I climbed into the backseat with the two girls while the guys continued their discussion. When Michael returned to the car he turned to me and said the girls are ready to go home.
As we headed toward the residential section of town I could tell from the deafening silence that the guys weren’t very happy about the way things were turning out. Once we dropped the two girls off at their respective homes Michael moved into the rear seat with me while Terry and Jeff stayed up front.
As we headed toward Micheal’s house where they intended to drop me off they began bitching about how disappointing this prom night had been. We passed the bourbon bottle around between the three of us. I say the three of us because by this point Michael was passed out in the back seat. I asked Terry to pull over so I could let the sl**ping Michael stretch out on the rear seat. Jeff got out of the front to help me get Michael arranged on the back seat. Once we had Michael as comfortable as possible on the back seat I climbed into the front seat between Terry and Jeff.
As we pulled away the guys once again began their complaining about what bitches the girls turned out to be and what a waste the night had been. I finally got tired of the bitching and I casually hiked the skirt of my borrowed prom dress up a bit higher on my thighs. I reached for Terry’s right hand and placed it on my left thigh. He gave me a quick glance and then began to slowly stroke my thigh through the pantyhose.
“I’m sick of all this pathetic bitching.” I said. “lets do something about it.”
I spread my legs a bit wider and allowed Terry’s hand to begin working it’s way up my thigh.
Terry was busy caressing my inner thigh and working up the courage to move on to my “clitty” tucked neatly inside my pantyhose covered panties. I took Jeff’s right hand and placed it on my right breast. He didn’t require any coaxing and I soon had one hand stroking my nylon covered crotch and another hand slowly squeezing and caressing my tits.
I told Terry to head for the 24 hour automated car wash which was just a block or so away. Once we arrived at the car wash we parked in the wash bay that was furthest from the street. I turned my back to Jeff and had him unzip my prom dress. I rose up from the seat the guys helped me to remove the dress. I dropped it onto the floor in the rear seat then I opened the passenger door and gently pushed Jeff so that he knew to exit the vehicle. I climbed out the door after him while Terry exited from the driver’s door. I instructed Jeff to sit down on the front seat with his legs out the passenger’s door. I knelt down and proceeded to open his pants in order to extract his young stiff cock. I bent down and began to lick the tip of his cock. After licking the head of his cock I let my tongue travel up and down the length of his shaft. I wrapped my lips around the cock and began to suck his cock deeper into my mouth. I let my head bob up and down on his cock, taking it deeper with each sucking motion. It didn’t take very long before his cum was spurting into my mouth. When his eruption subsided I leaned back on my knees and after showing him the large load of cum in my mouth I swallowed deeply and gulped the warm salty cream down my throat.
“ Girls spit.” I whispered to him “Women swallow.”
I stood up and walked around to the other side of the Cadillac to where Terry had been standing watching me sucking Jeff’s cock.
“Your turn Baby.” I said and Terry began to quickly open his pants and produced a [beautiful young cock. It was bigger and thicker than Jeff’s and it was quickly hard and long. He leaned against the side of the car and once again I dropped to my knees. I stroked his hard throbbing cock with my left hand while I wrapped my eager mouth around the bulbous head. He began to slide his cock in and out of my mouth in a rhythmic fashion. I hungrily sucked away on his cock taking every inch of it down my throat. Once again it didn’t take long for Terry to dump his cum into my mouth in big spurts. His seed filled my mouth and began to seep out from the corner of my mouth. Several drops dripped down my chin and settled on both my tits and the pink bra. I licked his cock up and down the length and all around the tip, allowing my tongue to clean every drop of remaining semen from his cock.
“So no more bitching about the lousy prom.” I said.
“Are you k**ding.” he said with a grin “This was the best prom ever.”
The guys helped me get back into my dress and we headed toward Micheal’s home. Once we arrived the guys helped me carry Michael to his bedroom. We deposited him in his bed and the guys prepared to leave. Before they left I kissed them both on the lips with a long passionate kisses and bid them goodnight. Once the pulled away I returned to Micheal's' room and struggled to remove his tuxedo slacks, shirt and shoes. I unzipped my dress and let it fall to the fall. After stepping out of the dress I rolled down my pantyhose and reaching behind my back I unhooked my bra. I slipped into Micheal's bed and spooned up against him. I still had unfinished business to handle. I still hadn’t made sure Michael had a great prom night.
As soon as he was awake enough I intended to suck his cock the same as I had done for his friends. The only difference was I intended to feel Micheal’s cock in “pussy” before we were done.








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Categories: First TimeShemales
Posted by chrissieCD
2 years ago    Views: 1,388
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2 years ago
Wish i had a prom night like this... incredible story!
2 years ago
Chrissie, That was priceless. I too laughed and had fond memories of "getting some" on prom night. Thank you for everything and I'm eagerly waiting to hear how receptive Michael was.
2 years ago
as always brill
2 years ago
As usual, great stuff! Very nicely done.
2 years ago
another great tale Chrissie! Thanks so much for posting!
2 years ago
Dear chrissie,

Another great story; I was laughing; it was great. Thank you.

Spanks and kisses,
Master Padraig