The Groupie

I am a mid 20's male college student, living at home in the midwest with my parents and my sister Amber. I just learned that my favorite female (sexy and beautiful) rock star ( we will call her Miss X) is coming to town next month and tickets are going on sale tomorrow at 10 am.

I decide to cut my morning classes and try to score a ticket on the internet the minute they go on sale. I am a little short on cash, so I ask my sister if I can borrow a few dollars. I am a little worried when Amber quickly says yes.

Amber is 19 years old, very hot and she knows it. I love her, and for the most part we get along, but 9 times out of 10 when she helps me out I owe her a big favor. This time was no exception.

"I will lend you the $150 for the ticket, but you have to pay me back $200," she says.

I tell her that seems very fair.

Then she adds, "Mom and dad are going away this weekend, and you have to let me and my friend Rachel have a party and have our boyfriends stay over."

I tell her, "Our parents will kill us if we have a party without their permission."

Amber says, "Well I guess you are not going to the concert. It's not going to be a wild party, just me, Rachel, and our boyfriends, and I promise no drugs."

"Where is everyone staying?" I ask.

She answers, "Me and my boyfriend sleep in my room, Rachel and her boyfriend sleep in your room, and before you ask, you sleep on the couch in the den."

I mildly protest, but agree. I really, really want to see this concert.

I am able to purchase a great ticket to the concert, 5th row center. I tell Amber the good news and she reminds me of the deal we made.

Saturday night rolls around. Amber and Rachel are getting dressed for their dates, while I nervously sit and watch television. The girls take turns showing me their outfits and asking me opinion. Rachel is much like my sister, gorgeous and knows it. I've had a crush on her for years, and she knows that too. She comes out wearing this hot sexy dress, thigh high stockings, a low cut blouse with her tits practically hanging out. Hot red lipstick adds a bit of slutiness to the look.

Then she says, "I would ask you how you like this outfit, but your erection gives you away. Maybe if you are a good boy I will let you sniff my panties after my boyfriend fucks me."

The boyfriends come over about 7 pm. My sister goes thru boyfriends so quickly that I never have time to learn their names, but she's been going out with this guy for awhile and actually introduces him to me. His name is Michael. Tall athletic type, seems like a nice enough guy.

We all make small talk for awhile, but it doesn't take long before Amber and Rachel are making out with their boyfriends, and then disappearing into the bedrooms.

I am sitting watching television listening to loud wild sex coming out of each bedroom. At one point Rachel comes out and says, "By the way, my boyfriend is bi, and he would love to have sex with you. He thinks you are cute, maybe in a girlish way, but nonetheless he thinks you are cute. Would you like to have sex with him? He has a really nice cock."

"NO f ing way. I am not gay"

Rachel says, "Ok, I will tell him maybe some other time. Your loss, but more cock for me. You can sit in the den, watch porn and jerk off."

I tell her, "I am not gay, I would rather jerk off than suck cock."

She just smiles and goes back to my room. Within minutes the loud moaning continues. I just end up falling asleep watching tv.

The next morning I get up early. Everyone is still asleep. I do a little cleaning up, but for the most part you can't tell that there was a party here last night.

Finally Amber comes out of her room and asks me, "When are mom and dad getting home?"

"Early this afternoon, but to be on the safe side have the boys out of here by noon."

"No problem. Michael has to go to work. He's taking a shower, the boys will be gone way before noon"

About an hour later the boys are getting ready to leave. They both thank me, and Rachel's boyfriend squeezes my ass. Rachel smiles, and after her boyfriend leaves she hands me a pair of her cum stained panties and says, "These panties are for you, smell them and see what you have been missing."

Then she kisses me and thanks me for letting her boyfriend come over.

Her and Amber help me finish cleaning the house, and when my parents come home there is no way they could tell that there was a little party last night.

Everything is pretty much normal the next few weeks. Rachel spends a lot of time at the house. I always feel that her and my sister are up to something. Rachel keeps teasing me about her boyfriend thinking I am cute.

The concert is now a week away and I am starting to get excited. Amber tells me some interesting news. It seems that Miss X is staying at the hotel where Rachel's sister works and maybe there is a chance I can meet her.

The next day, Rachel comes over to the house with her sister Christina. Christina starts telling us how Miss X, the band, and the crew rent an entire floor of the hotel, and maybe she thinks there is a chance she can help me to meet her.

Then she says, "But there is one major problem. Miss X is a lesbian, and she is only interested in hot woman coming to her room."

I am a bit surprised, but why should I question Christina. I thought Miss X had a boyfriend. She is always seen with good looking guys, very often making out with them.

Then Amber says, "I have an idea that might work. What if we dress you up as a woman? Then maybe Christina can get you up to her room. You have some feminine features, Rachel is good with makeup, and with a few days of practice I think you can pull this off."

I am very reluctant at first, but with Amber, Rachel, and Christina giving me encouragement I agree.

The next day after school Rachel comes over to the house.

"The first thing we have to do if shave all your body hair, starting with your legs, chest, and pubic hairs."

Amber and Rachel run the bath while I get naked. They start shaving my chest. Then my legs. It all feels very strange, but not as strange as having my balls and dick shaved.

Rachel likes what she sees, and says to Amber, "Your brother definitely has feminine potential. He may even make a pretty girl. Let him get use to his shaved body and tomorrow he will start wearing woman's clothes. Should we go with a conservative look, sexy, or slutty?"

Amber says, "I'll sleep on it, but we probably should try multiple looks and ask your sister what looks better. In the meantime he should at least wear panties to get use to his hairless dick. I think he might even like the feel of silky panties."

The following day Rachel comes over with a suitcase filled with clothes.

"My mom is about the same size as your brother. She has so many nice clothes that I doubt she will notice anything missing."

Then she asks me how I liked wearing panties for the past 24 hours.

I lied and said they were ok, but they actually felt amazing. I didn't want my sister and Rachel to know I was getting excited.

Rachel starts pulling clothes from the suitcase. She helps me put on a pair of pantyhose and a bra. My sister picks out a dress and helps me with that. We try on about 6 outfits in total. With every article of clothing they are more convinced that we can pull this off.

Amber says, "That's a pretty good start for today, I think tomorrow we should work on makeup, but for next hour or so we need to teach him how to walk in heels."

Rachel pulls out a pait of sexy shoes with about a 3" heel. I nearly fall flat on my face, but after an hour I start getting the hang of it.

Amber says, "You are doing great. Tomorrow we will work on your makeup. I will go out later and buy a wig. Do you want to be a blonde or a brunette?"

Next day we meet again, just two days before the concert. The girls dress me up again, trying on different combinations of dresses, skirts, blouses, panties,and stockings.

Finally Rachel asks, "Ready for makeup?"

I shake my head yes, and she says, "Ok, time to make you beautiful. Pay attention, Friday you may have to do this on your own."

I never realized how much effort went in to wearing makeup. A little powder, some blush, eyeliner, mascara, eye shadow. I am not sure I will ever be able to do this on my own. Finally some pink lipstick, and a blonde wig. Then I am told to look in the mirror. Wow, I look like a pretty woman if I do say so myself.

Moments later the front door opens. We had lost track of time and my parents had come home. I immediately panic. My sister sees this and says, "Don't worry, we got this. Follow my lead."

I have no choice now but to listen to Amber. She walks into the livingroom and drags me with her. Then she introduces me to my parents.

"This is my friend Brianna. She is here to help me and Rachel study"

My parents didn't bat an eye. We actually pulled this off. The three of us went back to my sister's room, pretending to study, and making plans for the next 48 hours. We decided that the next day Amber and Rachel would dress me up and take me to the mall to get my nails done. We would do a little shopping for any last minute items, then we would meet Rachel's sister and finalize the plans for the hotel and the concert.

Fortunately the next day I have no classes and the girls only have half a day. Amber and Rachel help me get dressed, but ask me to do my own makeup. I guess the practice had paid off and I am able to do the eye makeup and lipstick by myself. The girls are very impressed.

Rachel says, "You make a much cuter girl than you do a boy, I think you should stay this way. You would definitely have a more active dating life."

Amber agrees as the three of us get in the car and drive to the mall. We meet Christina about 2 o'clock. She is also very impressed, and we go straight to the nail salon. Christina suggests I go for the red nail polish, saying it's Miss X's favorite color. As I am getting my nails done I think the manicurist knows I am a guy, but Amber tells me I am just being paranoid. After we are finished Christina thinks it would be a good idea for me to walk around the mall by myself to get use to the idea of spending time as a woman. She gives me a few items to shop for, some makeup, a couple of pairs of panties and a bra. Again she thinks it's a good idea to not only spend time as a woman, but to do things women like to do, ie, shopping. We agree to meet for a bite to eat in two hours.

As I walk around the mall I realize that men are actually looking me over, and for some strange reason I am getting excited. I walk into the makeup store and buy a lipstick and mascara. Next I go into Victoria secret and pick out a couple pairs of panties and a bra. I still have an hour before I meet the girls so I just walk around the mall. I am getting more and more comfortable in my new role and am getting excited about Friday night. A man comes up to me, tells me I am hot looking, and asks for my phone number. I tell him I am flattered, but I am a lesbian. I think I just gave a guy an erection which makes me more excited.

I meet Amber, Rachel, and Christina at a restaurant in the mall to discuss Friday night plans. Amber and Rachel are to dress me at my house then Christina will pick me up and drive us to the hotel.

Christina fills me in on more details, "I met with the manager and tour promoter today. They always come to local hotels a day or two before the show to make sure everything is ok. They said that Miss X was excited to meet me. She is totally into hot red lipstick and she likes her women a little on the slutty side. She likes to get to the concert venue about 3 hours before the show, so she should be available to meet you between about 1 and 3 pm"

My heart is racing with every word Christina tells me.

"I don't know how to thank all you girls"

Rachel grins and says, "We will think of something."

I was so excited I didn't sleep a wink that night.

The big day comes. Amber and Rachel have taken care of every detail. Sexy panties, check. Matching bra, check. Stockings, check. After an hour the girls tell me to look in the mirror. I have a huge smile as I look at the pretty girl I have been transformed.

Moments later Christina comes by to drive us to the hotel.

She tells me. "You look so beautiful, this is going to be a day you will never forget. When we get to the hotel I will bring you thru the side entrance. Then I will bring you to the 8th floor where you will wait in the penthouse suite for further instructions."

We get to the hotel and take the elevator to the 8th floor. Christina let's me into the penthouse suite. What a room. Christina tells me that the hotel gets over $3,500 a night, and I am not surprised. I am waiting with Christina for about 5 minutes when there is a knock on the door. A man comes in and introduces himself as Alex, the tour promoter.

He says to Christina, "Brianna is even prettier than advertised, Miss X will love her. Thank you Christina, you can leave now."

Christina gives me a kiss, tells me to have fun, and leaves.

I am a bit nervous sitting alone with this strange man who seems to be a undressing me with his eyes, but at the same time I am incredibly excited. Alex senses my nervousness.

"Why don't you have a drink while we wait for Miss X?"

Alex pours me a drink. I relax a bit as Alex makes small talk. Then he sits next to me and rubs his hand up my leg while he tells me how beautiful I look. I can't believe how turned on I am getting from a hand rubbing my stockings, but I pull away when he tries to kiss me.

"Where is Miss X?" I ask.

Alex answers, "She will be here soon. I am just warming you up for her."

Then there is a knock on the door, and my heart begins to race again. But instead of Miss X, it's the drummer from the band, Ryan. At this point I am very confused and ask again, "Where is Miss X?"

Now I am sitting between Alex and Ryan. Alex is still feeling my legs, while Ryan is kissing my neck. For some reason I am turned on. I get more turned on when Ryan whispers in my ear, "You don't want Miss M, you want a couple of strong men with big cocks. Why else would you come to our room dressed like such a slut? Besides, what would make you think Miss M would be interested in a sissy like you?"

Totally confused, all I can think of saying is, "How could you tell I am a guy?"

Ryan explains, "Christina told us, plus that bulge in your panties kind of gives you away."

Wow, I just realized I had been tricked. But why? As I am trying to make sense of everything I am getting incredibly turned on and horny at the same time. Ryan is now making out with me, and Alex moves from my legs to feeling me up over my bra. My breathing is getting heavier as I get more excited. Then Ryan takes my hand and places it over his cock. Even thru his pants I can tell he has an enormous cock.

"C'mon slut, you know you want to suck it. Why else would you be wearing that cocksucker red lipstick?"

He pulls his giant cock out of his pants and I immediately start licking it. Then Ryan starts teasing me, slapping my face with his hard cock. I can't believe this, all I want to do is put his cock in my mouth.

"Beg for it." he says, "Get on your knees and beg for it."

I am getting so excited I do as he says.

"Please let me suck on your cock."

As I am sucking on Ryan's cock, Alex gets into the act. So here I am on my knees, one cock in my mouth and one in my hand. Then Ryan pulls his cock out of my mouth, lifts me up and throws me on the bed.

"Take your panties off and bend over you little whore."

I do as he says and before you know it I have a cock in my ass and another in my mouth. Ryan and Alex take turns fucking my ass and shoving their cocks in my mouth. I am so excited that I don't know which cock is which when suddenly one pulls his cock out of my mouth and cums on my face. I am still getting fucked in the ass for another 15 minutes when I hear a loud moan and feel a load of cum shooting on my butt.

I collapse on the bed.

Alex says to Ryan, "That wasn't bad for her first time, do you think she is ready for the rest of the band? Maybe, we can bring her backstage. You know how horny the boys get after a concert"

Then he asks, "Brianna, how would you like to give everyone in the band a blow job after the show? Maybe Miss X will watch."

I am so turned on I smile, lick my lips, and shake my head yes.

Ryan laughs then kisses me goodbye and leaves the room while Alex makes a phone call. Five minutes later Amber, Rachel, and Christina come into the room.

Amber asks, "How did Brianna do?"

Alex says, "She did amazing, are you sure it's the first time she has sucked cock?"

Then Alex hands Christina an envelope and says, "I promised you $500, but Brianna was such a good sissy slut I am giving you $1,000."

Christina takes the envelope and splits the cash with Rachel and my sister, but the math doesn't work exactly.

"$1,000 divided by 3 gives us $333 each with $1 left over" she says.

Then she hands me a dollar bill and says, " This officially makes you a whore. Be sure to thank Alex and Ryan for fucking you. And thank Amber and Rachel for dreaming up this wonderful idea, and by the way, next time Rachel tells you that her boyfriend wants to fuck you in the ass, you say YES."

I do say YES, then I thank Alex for fucking me and letting me suck his cock.

Amber says, "We better get my brother, I mean my sister, ready for the concert. We brought a change of clothes. Alex, can she take a shower and clean herself up?"

Alex says, "Yes, I will take good care of Brianna. There is an amazing shower in this room, and even a sauna. Brianna can relax here for a couple of hours then I will bring all you girls to the concert. Anyone interested in going backstage and watching Brianna suck off the band?"

All three girls raise their hands and say yes.