Blackmailed by Sister

I am a 22 year old male living at home with my parents and my 19 year old sister, Ashley. We both go a local college. I am the better student while my sister is more of a partier. I am a good looking guy, but have not had much luck with the ladies. I have a bit of a panty fetish and a lipstick fetish which may be the reason I am afraid to ask girls out.

A couple of weeks ago I was in the laundry room. For some reason I went thru my mother's dirty laundry and took a couple of pairs of panties. I tried on a pair and found myself getting excited. Next thing you know I was in my mother's bathroom and I took one of her lipsticks. Over the next week or so when I found myself home alone I would try on a pair of panties and put on lipstick.

One day my sister skipped some classes and came home early. She burst into my room and caught me red handed. I tried to explain that the panties were my girlfriend's and the lipstick on me was from making out.

"That's bullshit." She said. "First of all, you don't have a girlfriend, and second, mom asked me if I had taken any of her panties. At least now I can tell her it was you who took them. I wonder what she will say."

"Please don't tell mom." I begged. "I'll do anything. How about I do all your homework and write all your papers for the rest of the semester?"

"I think we can do better than that. I will have to sleep on it. Now stand there while I take your picture."

As she takes some pictures of me in my mother's panties and lipstick, I continue to beg, but Ashley would have nothing to do with it.

The next morning Ashley comes into my room with a smile on her face. I knew I was in trouble.

"What's up?" I asked.

"I was thinking. I really want to get into the sorority Alpha Phi. They are having a party in two weeks for all the new pledges, and then they will decide who they will let in."

"I am sure you will have no problem getting in, you are hot looking, and one of the most popular girls in your class. How can I help you?"

"Well, thanks for thinking I'm hot, but they are looking for more. Some of the guys from the fraternity house next door will be there. They are going to be judging a blow job contest."

"A WHAT???"

"Yes, a blow job contest. Each pledge must give at least 3 blow jobs, or find someone else that will do it for them. I asked a couple of my slutty friends, but they both said no, and I don't know who else to ask."

"How does that effect me?" I ask.

"Well, you like to wear panties and slutty lipstick. We just have to teach you to suck cock."

"I know some of the guys in that fraternity, they don't want me sucking their cocks."

"Don't be silly, they won't know it's you. I will take you shopping, buy you some panties, bras, and sexy lingerie. We can buy some makeup, a wig, a couple of nice outfits. You have some feminine features, I think you can pass as a woman."

"But I don't want to dress as a woman and give blowjobs."

"That's ok, you don't have to."

"Thanks"

Then Ashley takes out her phone and says. "I guess I will just have to show these pictures to mom and dad."

"OK, I'll do it, but you have to promise to delete those pictures."

"I promise, now let's go shopping."

We drive to the mall. First stop Victoria Secret.

"Let's find a sales lady. Make sure you let them know the lingerie is for you."

Ashley finds a sales lady. "My brother would like to buy some sexy lingerie."

"Is this for your girlfriend?" She asks.

"No it's for me. My sister wants me to dress for a sorority party."

"That's not the whole story." My sister says. "I caught him wearing our mom's panties and lipstick. He doesn't want our parents finding out, so he has to get dressed as a slut and give at least three blowjob at the party."

"Don't worry." The sales lady said. "You are not the first guy to come here to buy lingerie. Usually they say it's for their wife or girlfriend, but I can usually tell. That's one of the things of love about this job. Here is my phone number, my boyfriend loves sissy boys. He has a nice cock and he knows how to use it."

With the sales lady and Ashley's help I pick up a few pairs of panties, a couple of lacy bras, and a sexy nightie. Ashley makes sure everyone in the store knows the items are for me.

As we leave Ashley says goodbye to the sales lady, and says. "Wasn't that fun? We got lots of nice stuff."

"Yes it was fun, but I don't like being called a sissy boy."

"I caught you in mom's panties, wearing lipstick. Let's go to Ulta and get you some makeup."

We walk into Ulta, but this time my sister does the talking. She goes up to the counter and tells the woman. "This is my brother. I caught him wearing panties and lipstick. Now he wants to buy makeup so he can look like a pretty girl and suck cock."

The woman looked a little shocked, but quickly regained her composure. "We have a makeup artist in the back. If you can wait about 10 minutes she can give your brother a makeover."

"That would be great." My sister said. "In the meantime we will just walk around the store."

As we walk around the store I have no idea what half the stuff is, but I have to admit I get a little excited when I walk past all the different lipsticks.

About 15 minutes later the woman asks me if I am ready for a makeover. She takes us to the back of the store and introduces us to Lacey. She is an attractive woman in her mid thirties. She has me sit in a chair and then she talks with Ashley for a few minutes.

She tells me I have some feminine features and she promises she can make me into an attractive young lady. She puts some moisturizing stuff on my face, followed by some blush. "You have such pretty blue eyes, watch me make them feminine and sexy." A little eyeliner, eye shadow and mascara and next thing you know I have beautiful eyes. Then she hands me a hot pink lipstick and says. "I know you have put on lipstick before, let me see you put this on."

I am so turned on at this point I take the lipstick and put in on.

"Not bad." Lacey says. "We will teach you how to be more seductive next time. Remember you want to get the fraternity boys excited." Then she sits me back in the chair and takes out a blonde wig. She puts it on my head then tells me to walk over to my sister.

I see Ashley in the lipstick section and walk over to her. She does a double take. "Wow, is that you? You look hot."

We walk back to Lacey, and Ashley congratulates her on the job she has done.

"One more thing." Lacey says. "We need to give her a proper name. How about Brianna? It's hot and slutty."

"Love it." Says Ashley. "C'mom Brianna we still have some shopping to do. Need to get you a nice dress for the party and some stockings. Becoming a woman is so much more than just wearing lipstick."

Next stop is a nice woman's boutique store. Ashley picks out a couple of dresses, one conservative and one slutty. She had me try them both on in the store dressing room. When I came out of the dressing room to show her I noticed some guy looking me over. I don't know if this made me nervous or excited. As we left Ashley picked out a few pairs of stockings and pantyhose and then as we were on line waiting to pay she told everyone the story of how she caught me wearing my mother's panties and lipstick.

On the drive home Ashley asked if I was having fun.

"Clearly not as much fun as you." I answered.

"I had a great time, I can't wait to do this again. When we get home we are going to shave all body hair. No fraternity brother wants to get his cock sucked by a hairy girl."

When we got home Ashley ordered me into the shower and started shaving my chest and then my legs. "You will love the feeling of wearing stockings now that your legs are shaved."

I just smiled, I wasn't ready for what came next.

"Now it's time to shave your pussy."

"It's not a pussy." I protested.

"It is now, just be still while I shave you."

After she carefully shaved my pubic hairs Ashley handed me a pair of lacy pink panties that we bought from Victoria Secret.

"Put these on."

"They feel amazing." I confessed.

"I told you that you would love them."

Then I told her something that in hindsight I might later regret. "I have a confession to make."

"What, Brianna?"

"A few weeks ago I came home early and saw you giving your boyfriend a blowjob."

"Which boyfriend?"

"I can't remember the names of all you boyfriends. But seeing your hot lipstick wrapped around his cock really turned me on. And when he came down your throat, I thought wearing lipstick and sucking cock might be something I might want to do. That's when I took mom's panties and lipstick. I guess I wanted to be like my little sister."

"That's quite a confession. And trust me, once you swallow a load of cum you will be hooked. Do you remember which lipstick I was wearing?"

"I think it was the red one."

"That must have been Tommy. He has a nice cock. Did you like it?"

"Yes, it's much bigger than mine. Are you trying to tell me you wear different lipsticks to suck different cocks?"

"Of course. Red for Tommy, bright pink for David. Maybe you should change your lipstick between blow jobs at the party next week. We are getting distracted, time to get you dressed and teach you how to become a young lady. The party is in two weeks."

Ashley takes out a bra. "This will match your pink panties. I will help you put in on, but in the future you will have to do it yourself."

She puts the bra on me. "Look it makes you look like you have tits. The frat boys are going to love to feel you up." As she is talking Ashley squeeze my breasts over the bra. It feels amazing.

"Look, Brianna has a bulge in her panties. If you like this wait until those big strong boys squeeze these."

Next my sister helped me put on a pair of stockings. She was so right, they felt amazing over my shaved legs. Then she helped me put on a very sexy short dress. She sat me in front of the mirror in her room and started with my makeup. Much like the makeover at Ulta I had no idea what was going on, but 15 minutes later my sister put a blonde wig on my head and told me to look in the mirror. WOW, I couldn't believe that I looked like an attractive woman.

"I don't know what to say, I can't believe I can pass as a woman."

"You can say thank you, but we still have work to do. In the meantime I have a little surprise for you."

Next thing, she pulls out a dildo. "You can practice sucking on this until we can get you the real thing. I am going to show you some blow job porn, pay close attention."

So she opens her computer and pulls up some porn website. A hot blonde with slutty red lipstick has a huge cock just inches from her face.

"Notice how she gently licks the head of the cock, then licks up and down the shaft. Guys love that. After you get them nice and hard try to take the whole cock in you mouth."

I take the dildo, kiss the tip, lick up and down the shaft, and with Ashley's encouragement shove the entire thing down my mouth.

"Not bad, but there is room for improvement. Mom and Dad will be away this weekend, maybe I can have some friends come over and help you practice. In the meantime let's work on your dressing up and makeup skills."

Friday evening our parents are packed and ready for a weekend getaway. They give us the usual speech. "No wild parties, yada, yada, yada." I help them with their suitcases and we wave goodbye.

The car has barely pulled out of the driveway when Ashley grabs my hand and says, "Let's get you dressed and have some fun."

We go upstairs and Ashley picks out some clothes for me to wear. A half hour later I am transformed into an attractive young woman.

"Ok" says Ashley. "Let's go to the mall and do some last minute shopping."

"I am not sure I am ready to go out dressed as a woman."

"Don't be silly. I need to do some shopping, you need to get your nails done. Besides what young lady doesn't love going to the mall."

Our first stop again is Victoria Secret. Ashley needs some panties and is hoping that the sales lady who helped us before will be there.

The woman is there and immediately recognizes Ashley. Then she looks at me and does a double take. "Is that your sissy brother?"

"Yes, please call her Brianna."

"She looks good, has she sucked cock yet?"

"No, the party is next week."

"Have fun, remember my brother loves sissy boys."

"I remember, we are going to get our nails done now. I will keep you posted on our progress."

Ashley takes me to the nail salon. The manicurist recognizes her and asks why she hasn't been in lately.

"I've been busy with school, but I have a big party next week and I need to have my nails done."

"It's good to see you, who's your friend?"

"This is my brother, Brianna. I caught him wearing panties and lipstick, now he is my little sissy. This is her first manicure, but it won't be his last."

"What color should we do?"

"Pretty pink to match her lipstick."

So I sat there basically silent while the manicurists all fussed over me and Ashley. It actually felt really nice having my fingers and toes massaged and painted. I think the girls noticed I was getting an erection.

On the drive home Ashley has an idea. "All this talk about sucking cock is making me horny. I am going to invite Tommy over to the house. You can watch me suck his cock, but you will have to leave the room when he fucks me. I won't tell him you are my brother, I will just introduce you as my cousin Brianna from out of town."

When we get home Ashley spends a few minutes fixing my clothes and makeup. About 10 minutes later the door bell rings. Ashley puts on her slutty red lipstick and answers the door.

She gives Tommy a big kiss and then introduces us. "Tommy, this is my cousin Brianna. She is kind of shy. She just met some guy that she really likes. The guy wants to have sex, but Brianna wants to stay a virgin. As a compromise Brianna has agreed to give him a blowjob, but she is afraid if she doesn't suck cock well the guy will break up with him."

Tommy says. "I didn't think you knew any virgins. As she at least given him a handjob?"

"He felt her boobs while she rubbed his cock thru his pants."

"Wow, you were doing that in junior high school. By the way, I love your lipstick, and Brianna's is pretty hot too."

"Thanks, here's the story. I am going to suck your cock. Brianna is going to watch and hopefully learn."

We go upstairs to Ashley's bedroom. Her and Tommy start making out. He takes her shirt off and starts sucking on her tits as my sister starts moaning. She pulls his pants down and takes out his cock. It was huge.

"I think Brianna like this." Tommy says as he strokes his cock.

Ashley starts kissing the tip of Tommy's cock and licking up and down the shaft, just like in the porn video. Then she takes his entire cock in her mouth and starts sucking while Tommy is moaning louder and louder. It's a good thing he is not looking at me or the bulge in my panties would give it away that I am not a female.

Ashley stops sucking for a moment and takes Tommy's cock out of her mouth.

"I hope you were paying attention, but now it's time for you to leave. Go into my brother's room while Tommy fucks me."

I go into my room. I can hear Ashley's moaning getting louder and louder. As she screams, "I'm cumming." I cum in my panties.

A few minutes later Ashley calls me into her room. I quickly change my panties, walk into my sister's room to see her and Tommy completely naked.

Ashley says, "We have a surprise for you."

"What?"

"Tommy used a condom. It is loaded with cum. Freshen up your lipstick, open your mouth and taste your first load of cum."

I fix my lipstick, as I walk over to the two of them and open my mouth Tommy takes the condom and let's the cum drip in my mouth.

"Swallow." They both say.

I swallow my first load of cum, much to the delight of my sister.

The three of us hang out for awhile, then Tommy gets dressed and kisses Ashley and me goodbye.

After Tommy leaves Ashley sits me down for a minute. "Tommy thought you were hot. He never guessed you were my brother, and He has lots of friends on the football team that would love to get their cocks sucked. There is one problem."

"What's the problem?"

"I noticed that bulge in your panties. If anyone notices you are a guy I will never get into the sorority."

"What do you want me to do?"

"If you can't control yourself we might have to put your cock in a cage. In the meantime, you should probably give a real blow job or two before the party. There is a porn shop in the city with a glory hole. A couple of my friends have gone there to learn how to suck cock. It's a great place to practice, and if your dick gets hard nobody will notice."

"What's a glory hole?" I ask.

"It's a room in the back of a porn store where you can watch dirty videos. There are some holes in the wall where total strangers stick their cocks and get blow jobs. It's kind of hot."

"Have you done that?"

"Of course, how do you think I got to be so good at sucking cock. We will go tomorrow. You will love it."

To be continued.