Double Date with my Sister

It was 1977, I was a 18 year old senior in high school. I lived out of town on a farm with my sister, mom and dad.

My sister was a senior also, had been kept back a year and with prom coming up, was making her own dress for it.

She had a boyfriend, Tom, who was going to the prom with her. Tom was a total jock, stood 6'3" tall and weighing 225 lbs.

I wasn't into sports, wasn't big enough to bother with it. At 18 I was only 5'4" tall weighing 135 lbs. My sister, Marie, was same height and weighing 139 lbs.

Like most guys back then I had long hair, just over my shoulders with bangs that was a light brown color. What little extra weight I had was on my bubble butt, from behind I looked like I had a girls ass.

We was on our spring break, both our parents worked, me and Marie home alone. Marie was working on her dress. It was a blue with white polka-dot a-line dress with a sweetheart neckline and short puff sleeves.

I was sitting watching tv and talking with her. "Ok, wow getting closer to getting my dress done," she says.

"Oh yeah, what do you have left to do?" I ask.

"Not much, can't go much farther until I set the hem, mom will have to do that while I have it on, sucks because she works till 9 tonight. Could have it done by then." Marie says.

"That sucks, having it that close and have to wait a day." I say looking at her.

She is looking at me kinda weird.

"You know you and I are close to the same size, I could set the hem now if you would help me." She smiled.

"Sure, I'll help, what do you need?" I ask her.

"For you to put it on and stand on the coffee table," she said.

"That ain't happening," I tell her.

"Oh please Brad, I want to finish this dress so bad," she says.

"Still not happening," I say.

She sits thinking. "Ok, you know Lisa Kusterman and I are good friends, and I know you have the hots for her. How bout if I get her to show you her tits, would you do it then?" She asks.

Every guy had a thing for Lisa, including me. I was still a virgin, hadn't seen any real boobs. "If you promise to never tell anyone and get her to show me them, then I will do it " I say.

"Of course I promise Brad," she said.

"Ok then let me know when you are ready," I say.

"I am right now, I'll get you the stuff you will need to put on under the dress for me to get it the right length," she says getting up going to her room.

I wasn't listening to her, not thinking at all.

Marie comes back with some clothes. "Ok, to get it to hang right on you you will have to put on this bra and panties and this white full slip over them. And we will have to stuff the bra cups to my size boobs " she says.

"No way, I wont even put that on," I say.

"Please Brad, ok, ill even talk her into letting you touch her boobs." She says.

I started to get a hard on at the thought of touching Lisa's boobs. "I can't believe I'm saying yes, but ok its a deal " I say. Marie handed me the lingerie.

I take it going to my bedroom and taking off my clothes. I then slowly slipped the white panties up my legs and ass to my waist. Next with some time I finally got the bra on, the cups looked funny with no boobs in them so I stuffed them with a pair of my socks. Finally I pulled on the pink full slip over my head and down my body. its hem fell to mid thigh.

I looked at myself in the mirror rubbing my hand over the silky slip. I freaked out when my cock got hard. I couldn't let Marie see this. I decided tucking it back between my legs in the panties to hold it there and did it.

I slowly walk back to the front room. "Ok now you can laugh at how bad it looks," I say walking in so she could see me.

Marie looks at me and has a surprised look. "Omg Brad you don't look bad at all, in fact makeup and hair done right you could pass for my younger sister." she says.

I walk up in front of her and she stands helping me step into the dress, once on she turns me and zipped it up.

I then stand on the coffee table and she pinned up the hem of the dress. "ok, its set, oh wait I really need to see if its right height when my heels are on." She says.

Marie goes to her room comes out with a pair of blue pumps with 3" heels.

Ok step down and sit, rest for a minute and put these on." She put the shoes on table in front of where i sat.

"I can't believe I'm doing this, " I say setting the heels on the floor. I tried one foot and you could tell it would fit but my sweaty feet wasn't going in them.

"Ok, hold on," Marie says going back in her bed room. When she came back she had a pink garter belt and a pair of white stockings. "Ok, put these on and then you'll be able to get them on."

I easily get the garter belt on, then Marie helped with the stockings hooking them to the garter tabs.

I then had no problems getting the heels on my feet.

I stand up and look at Marie, "Omg Brad, turn for me," she says. I turn all way around.

"I totally hate you," she says standing behind me. "Your ass looks so much better than mine."

I could see myself in the mirror as she fixed the hem. I couldn't believe how much I looked like a girl. I get hard looking at myself, my cock pulls out and up in the front of the panties I had on, doing it as I faced Marie.

"I uhh, im sorry," I stutter when I see that she had seen I was hard.

"I see you like dressing up as a girl, it's cool Brad if you like guys, I don't mind," she smiles. "Im done, lets get my dress off you before you stain it," she says unzipping it and helping me step out of it. Marie holds her dress looking at me.

"I don't like guys, I like girls." I say.

"Please let me curl your hair and put makeup on you, don't you want to see what you would look like as a girl?" she asked me.

I did at this point. "You won't ever tell anyone?" I asked. She shook her head.

30 minutes later she had curled my hair and had makeup on my face, hadn't let me see myself. "Omg Brad you are a pretty girl, you would have guys hard just looking at you." she says letting me see.

I freaked seeing the sexy girl in the mirror. "Omg, I think you are right, I could get guys hard." I blurt out as I get hard in my panties again.

"I want to watch when you give your first blow job, that be so hot," she says.

I don't know why I was thinking about me sucking a guys cock, but I was. "I bet when he cums in my mouth it would be gross." I hear me say.

"Never know, why don't you lick up the load I known you are ready to shoot," she says. "Go on do it in your room," she pointed to my door.

As quickly as I could in the heels I go into my bedroom. Sitting on my bed, legs spread I rub over my hard cock in the panties, cumming in about 10 seconds.

I had shot my load in the panties I had on. I slowly lower them down my legs. I look at the cum spot inside them, then just did it, I licked my cum from them. I pulled my slip down over my cock and panties in hand go back out, putting her panties in the hamper. Walking in the heels made me feel sexy feminine. I go sit on sofa, Marie sat in recliner.

"You don't have to change if you don't want to Brad," she says tossing me a clean pair of red panties.

I stand putting them on.

Marie and I sit and talk watched tv until bedtime.

"You want a nighty to wear to bed Brad?" She asked.

"Yes please ", I say.

I go to bed wearing a pink and black nighty with matching panties. I dreamt about doing it with guys all night.

Mom and dad already gone to work when I got up. Lisa and I shared a bathroom. I sit to pee pulling panties up tucking my cock between my legs.

Looking in the mirror I brushed my hair. it still kept curled hair effect making me still look like a girl. I put on some mascara and lipstick.

I walk downstairs to the kitchen where I figured Marie was. She was in there, but to my surprise so was Tom her boyfriend. We all looked in shock at each other.

"Lisa you didnt tell me you had someone spend the night", Tom says. "So who are you?" he asks me.

"I forgot to tell you Tom that my cousin Brandi was here for a week," Marie says winking at me.

"Wow, ok, how old are you Brandi?" Tom asks looking at me.

"Im 18," I say in my best girly voice.

"Cool, my cousin Josh is here for a week, you two are the same age, we can all hang out together," he says. I was freaking out.

"Ive got to go help Dad today, 6 ok to pick you guys up?" He asks.

"Yes that be perfect, "Marie says.

Josh leaves.

"Omg Lisa, what are going to do?" I ask freaking out.

"Sounds like we are going on a double date, why did you come down here dressed up?" she asks. "No way out of it either, so Brandi you are going on your first date."

I tried talking Marie out of the double date deal all day. Marie finally tells me if I don't go she would tell everyone about the day before.

"I'm not into guys at all," I tell her.

"I believe you, but to get what I want from Tom I have to find a date for Josh, and you are his date." She tells me.

"Look, its a first date between two kids that are virgins to dating and all. So, Josh isnt going to try anything, especially if you don't show any interest." Marie tells me. "You do this for me and I will get you laid by a girl."

"Ok, ok, ill do it," I finally said.

It was 4pm when I showered shaving off what little body hair I had. I put my hair up in a towel and dried off wrapped the towel around my waist. I walk in to the front room where Marie sat.

"Ok, here take these and put them on in your room," she says handing me a blue bra and panty set with a pair of black pantyhose.

I take the lingerie to my room putting it all on. I look at my sexy body in the mirror. I had tucked my cock back between my legs, it started getting hard.

I walk back to front room seeing Marie had moved to her room. She had me sit in her vanity chair turned away from the mirror.

Lisa took my hair out of the towel and combed it out. She then curled it with a curling iron and blow dried it.

Next came eyeliner, mascara and green eyeshadow. Then came a pink lipstick. Then she clips on a pair of long earrings, necklace and bracelets.

"Ok, wow Brad, you look so pretty," she says finally letting me stand up and look in the mirror.

"Omg, shit I look like a pretty girl," I say looking at myself.

Marie then had me step into a light green floral print dress and pulled it up and on me zipping it in back.

It fit me perfect, the neck was v shaped, snug bust, waist down falls in a full tiered skirt falling to about 3 inches above my knees.

"You look so good as a girl," shs says giving me a pair of blk ankle strap pumps with 3" heels to put on.

I sat and straped them on and stood up.

"Ok, practice walking in them while I get ready." she tells me.

Lisa gets ready, also wearing a dress and heels.

"I don't think I can do this, " I tell her.

Lisa gets a pint of vodka out from a hiding spot in closet. "Take a drink," she does one handed to me, we took 3 shots apiece and shortly I calmed down.

Lisa got 2 bottles of finger nails polish, green for me and red for her. We did our nails and taking shots of the vodka.

"We switched it up, now we are supposed to meet up with them in Paris," Marie tells me.

Marie goes and gets 2 purses putting makeup and such in each one. Hands me one, "get your ID and some money in case you need it," she says.

It was 5:45 when we got in her car driving the back roads to Paris.

We cruise Paris about 15 minutes till we met a black 69 Charger. Marie honks at it. "Omg thats Tom!" She screams.

Tom does a u-turn following us to the mill parking lot. Tom was alone as we park by each other, driver's facing each other.

"Where is Josh?" Marie asks.

"Well pretty ladies, right there he comes." Tom pointed as a jacked up Chevy short bed pickup pulls in. He pulled up to my side rolling down his window.

"Hi, I'm Josh, I bet you are Brandi," the long blonde haired guy says.

"Yes, nice pickup," I say smiling.

"And you are prettier than Tom said," he says. I couldn't help my blushing.

We all sit talking and passing a joint and a bottle of wine back and forth. I was getting fucked up.

"So, can I drive your truck?" I asked Josh.

"I don't think so, but you can take a ride with me.

I look at Marie. "Are you sure?" She asks.

"Yeah, Ill be ok," I say.

Josh backs up and I get out fixing my dress. I opened passenger door stepping up on the side bar pulled myself up and into the tall 4x4 sitting fixing my dress.

"Wow Brandi love ur dress," Josh says smiling at me.

"Thanks, " I blush.

We take off talking and sipping the wine.

"Im so fucked up," I say.

"Have you ever done any ice, it will make you sober again," Josh asks me.

"No, but I'm ok with trying it, " I say.

"Ok, cool, I'll drive out in the country and park to do it," Josh says heading out of town.

We stop backing into a field entrance, he turns truck off.

He gets a leather case from under the dash pulling out a glass pipe. "Seeing how you haven't done this before we should shotgun my hits," he says.

Shotgunning hits meant him taking hit then holding our lips close together I suck in the smoke he blows out.

Josh lights the lighter holding to bowl taking in a big hit. Then motions for me to get closer, I do it our lips a couple inches apart as he blows out and I suck it in and hold it.

I could feel it almost instantly. I exhaled.

"Very good, ok again," he says taking the hit. I move closer to him. He turns, this time was only like a inch from my lips and gives me the hit. We do 2 more, I could feel its affect good, I was getting sober, higher.

"I cant believe how totally hot and sexy you are Brandi," Josh says.

I don't know why but this started to turn me on.

"I've wanted to kiss your pretty lips from the minute I first saw you," he says taking a hit.

"Nobody here to stop you from it," I hear me say turning to him. I couldn't believe I had said that.

Josh leans to give me the hit but this time presses his lips to mine blowing the hit into my mouth, then pulled away.

"Wow, its so hot in here," I say.

"This stuff will make you hot, lets get out and sit on the tailgate," he says.

"Ok sounds good," I say. We both get out of pickup meeting in the back.

Josh puts tailgate down and the pickup was so high that the tailgate was above my waist.

"You have a bucket I can step up on?" I ask him.

"No, here turn to me," I do and without warning he picks me up at my waist sitting me on the tailgate.

"Wow, ok," I say. I noticed then how tall Josh was, me sitting up there he stood even in height with me, I smile.

"You have a pretty smile Brandi," he says leaning to me we kiss. I couldn't believe I was kissing him. Without thinking I take my arms wrapped them around his neck as we kiss, pulling him closer. Josh just reaches down pushing my legs apart so he could stand between them as he wrapped his arms around my waist.

I knew I should have stopped him but kissing him was turning me on so much. My cock was hard between my legs in my panties. I started wondering if Josh's cock was hard to, even worse I wondered how big it was.

I slide my hands down to his chest rubbing it thru his t-shirt feeling his hard pecks. I freaked when he stops our kiss and pulled his shirt off.

Josh slides me off the tailgate so I'm standing in front of him and started kissing me again. I was so turned on.

I reach between us and rub over his big cock in his pants making him moan.

Josh's big hands slide around to my ass rubbing over it, then down and up underneath my dress rubbing my ass.

I don't know why but I started undoing his pants. Once undone he quickly pushed pants and all down his legs. His big cock now had my hand wrapped around it stroking it.

His hands went back up my dress in back to my waist hooking waistband of my pantyhose pulling them down over my ass. Then he does the same to my panties.

Josh stops our kiss and spit on his 2 fingers and I feel them push thru to my hole as he kisses my neck.

His big cock had leaked out so much precum that my hand easily slid up and down it. I couldn't believe I was pushing my ass back towards his fingers.

Josh just pushed a finger into me. I should have stopped him already. "Omg Brandi ur so hot and sexy, I want you so bad, please let me fuck ur ass, you can't get pregnant from getting it in your ass," he whispers in my ear. "I want you to be my girlfriend."

I dont know why this all turned me on so much, and omg his finger wiggling in my hole felt so good.

"Yes Josh I want to be your girlfriend, " I whimper humping my ass on his finger. "Please fuck me, I want to feel your big cock inside me. "

I turned, feeling his finger come out of me, facing the tailgate I pull my dress up over my hips, pulled my panties and pantyhose down farther. Spread my legs as I lean over the tailgate.

Josh stepped up behind me his cock sliding up and down along my crack, precum lubing it up. I reach back grabbing his cock pulling it out straight and holding its fat head at my hole.

Josh grabbed my hips and slowly pushed his cock head into my ass.

"Oh, ow easy Josh this is my first time!" I cry out when his fat cock head pushed into my ass.

"Ok, I'll just let you decide when you want more," he says.

I really wasn't sure at first what he meant, but realized when he hadn't pushed his cock any further that he expected me to push back to him to control how much pain I could stand.

I push back feeling about a inch slide in me, I wait till I was comfortable with it, then do it again and again till I felt his balls against my ass.

After a few minutes I started wiggling my ass around on his cock. "Omg Josh, wow your big cock is so deep inside me, it feels so good!" I cry out and started humping my ass a little feeling his cock sliding in and out of me a couple of inches.

"Oh yeah Brandi, yes work ur sexy ass on my cock," he says.

I slowly started increasing how deep I had it sliding in and out and going faster. Omg yes Josh, mmmmm fuck me baby!" I yell as he started working with me sliding his big cock in and out of me, our bodies slapping together now.

I suddenly realized how hard my cock was in the front of my panties when it's rubbing in the panties and me getting more turned on, I was going to cum soon.

"Omg Josh, Im going to cum even with you in my ass baby, and im going to cum soon, oh god Josh please cum with me!" I scream.

Josh slams into me and holds my ass back to him all his big cock was deep inside me. I feel it start throbbing and jerking deep inside me as he cums.

Right then I scream out as I shoot my load in my panties.