Blackmailed by Sister Pt. 02

My sister had come home early from school and caught me wearing our mother's panties and lipstick. After thinking about it for a day she decided on a punishment. She badly wanted to get into one of our school's top sororities. In a few weeks there would be a party. Fraternity brothers from the house next door would be judging a blow job contest. Sorority pledges would have to suck three cocks, or find someone who would. Ashley thought that since I already enjoyed wearing women's clothes I could be feminized and pass as a woman and learn to suck cock.

Ashley enjoyed taking me shopping for clothes and makeup and embarrassing me in front of sales ladies. I made the mistake of confessing that I enjoyed my feminization.

Next Ashley needed to teach me how to suck cock. We practiced on a dildo and watched blow job videos. Finally Ashley invited a boyfriend over and had me watch as she put on slutty lipstick and sucked his cock.

After her friend left Ashley took me aside and seemed upset. I had become so excited I came in my panties. "You are lucky that Tommy was distracted and didn't notice your cock was bursting out of your panties. If that erection gives you away it would cause great embarrassment at the sorority party for the both of us."

Her solution was to put my cock in a cage, which could be painful, or practice sucking cocks until I can do it without getting abulge in my panties.

Then she got a brilliant idea. "We will go to a porno shop in downtown where they have glory holes."

Well, maybe I am naive, or maybe my sister was a bigger slut than I thought, but apparently that's where Ashley and some of her friends learned to suck cock.

"Get a good night's sleep, tomorrow is going to be a busy day."

Needless to say, I didn't get much sleep. I watched a couple of porn videos about glory holes to see what I was getting myself into.

Ashley walked into my room at about 10. She was dressed in a hot mini skirt, fishnet stockings, and hot pink lipstick. "We are going to try something a little new today. I am going over to Tommy's house this morning. He has a friend over for the weekend, and he asked me to come over for a threesome. While I am gone I want you to get dressed all by yourself. I have laid out the clothes for you to wear. Make sure you shave your legs and your pussy. If you have any questions give me a call, I will be home in a few hours. And no jerking off!"

Ashley knew me too well. As she left I jumped into the shower. It had only been a few days since my legs had been shaved so that went fairly quickly. After I dried off I went into Ashley's room to find the clothes she laid out for me. Sexy black panties and black bra. I still had trouble with the bra, but I am getting better. Same can be said for the pantyhose, but I managed. Next I put on a very pretty red dress. I then sat in front of her mirror and attempted to put on makeup. I put some blush on my cheeks. I tried to put on some eye shadow and mascara, but I gave up and texted Ashey. She quickly texted back. "Don't worry about it. Do the best you can and I'll fix it later. Just put on your lipstick, see you in a couple of hours."

I then put on hot pink lipstick and some lipgloss. For some reason wearing lipstick made me want to suck cock. I put on the blonde wig, looked in the mirror and waited for Ashley to come home.

About an hour later Ashley comes home, hair and makeup a mess. I ask how her threesome went, she just smiled.

She complimented me on how well I was able to get dressed without her help. "You still need help with you eyes. I will help you later. I'm a little tired right now, let's relax for a few hours then I'll help you get ready for your first glory hole."

Ashley took a quick shower, then took a nap for a couple of hours. About 5 o'clock she came into my room. She was wearing a hot very short dress, thigh high stockings, and my favorite slutty red lipstick. She helped me with my eye makeup. Mascara, eyeliner, and eye shadow. "You do have beautiful blue eyes, eventually you will be able to make them sexy and feminine without my help. Now go freshen up your lipstick and get going to the city."

There was a bit of traffic driving to the city. Ashley spent much of the hour drive talking about her sexual adventure earlier in the day. Hearing my sister's slutty stories was getting me excited, and taking away the nervousness of going to the glory hole.

Eventually we get to the porno store. It's in a sleazy part of town, but the store itself is actually pretty nice. We walk inside. There are a few men looking thru the x rated videos and a man and woman looking at some sex toys. The man behind the counter is well dressed. He says,"Hi Ashley, long time no see. Who's your friend?"

"This is my brother Brianna. I discovered he, I mean she, likes to wear panties and lipstick. Tonight he is going to learn how to suck cock."

"Wow, she can certainly pass as a woman. Love the slutty lipstick. Why don't you go to room 5, I will put on some sissy videos. There are a lot of cocks waiting."

"Thank you."

We walk into the room. There are some holes in the wall, and a video playing on the screen. The video is about a husband is forced to crossdress and then suck her lovers cock. I was really getting turned on watching the sissy husband getting dominated when a cock popped thru the hole in the wall. My sister talk my hand and plced it on the cock. She had me stroke it, then she told me to lick the tip, lick up and down the shaft, and finally put the entire cock in my mouth. She encouraged me to move my mouth up and down as I could hear heavier breathing from the other side of the wall. Moments later he shot a giant load of cum down my throat. Seconds later another cock appeared. Ashley encouraged me to suck it without the benefit of her assistance. I tried to remember what I was taught. Stroke the cock, lip the tip, lip the shaft, put cock in mouth and start sucking. A few minutes later I had swallowed my second load of cum. When I third cock popped thru another hole. This cock was much larger than the other two. As I crawled over, Ashley stopped me. "This one may be too big for you. Watch and learn as I suck it."

Ashley starts sucking cock like there is no tomorrow, and in less than a minute the cocks cums in her mouth. She licks her lips and smiles. "One more cock and we will call it a night. But this time when you hear the breathing get heavier and you feel like he is about to cum I want you to take his cock out of your mouth and let him cum on your face."

After about ten minutes there hasn't been a cock poking thru a hole. Watching the sissy video the feminized husband is sucking on a cock while another man is spanking his ass. Then a third man bends him over and starts fucking his ass. Ashley says. "Don't get too excited, you are not ready for that. I want my brother, I mean sister, to stay a virgin until she meets the right guy."

I must admit I was getting excited. Just then a huge cock popped thru a hole.

"Go get it girl!" Ashley said giving me encouragement.

I start kissing, licking, and sucking. I heard breathing and moaning from the other side of the wall.

"Take his cock out of your mouth."

Ashley was the expert and I did what I was told. Seconds later a big load of cum shot all over my face.

"Now lick the rest of his cum off the tip of his cock and say thank you."

"Thank you for cumming on my face."

"Ok, time to go. Make sure you thank Bob behind the counter."

As we leave the store I smile and thank Bob.

"How she do?" Bob asked my sister. "That's quite a load of cum she has on her face."

"She did pretty well for her first time, but she needs a little work before the sorority party. We may have to come back during the week."

"You are always welcome here."

"In the meantime I think I need I need to buy Brianna a cage for her cock, she is still getting a hard on."

Ashley picks out a couple of cages. As she goes to pay Bob says. "That nice gentleman just paid for them."

Ashley thanks the gentleman. He smiles, blows me a kiss, and hands Ashley his phone number.

We get into the car to head home. Ashley gives me a wet nap and tells me to wash my face and fix my makeup.

"What do you mean I still need work?" I ask.

"It takes more than sexy lingerie, makeup, and sucking cock to be a woman. There is still work to be done before the party. There is a lot at stake for both of us. If you can't pull this off I won't get into the sorority, and you will just be known as the campus sissy slut."

"No pressure, thanks. What else do you want me to do?"

"There's a bar around the corner. We can hang out for an hour or so. Get some guys to buy us drinks, flirt a little then go home. Let's see if you can pass as a woman. If you can't there's nobody there that will know us and we can drop this plan."

We drive around the corner and pull into the bar parking lot. Ashley fixes my hair and makeup.

"Just to be on the safe side I am going to put this cage on your cock. This should keep you from getting an erection."

Fortunately the lighting in the parking lot isn't too bright. Ashley pulls up my dress, pulls down my panties and puts on the cage. It's uncomfortable, but Ashley says I will get use to it. I was going to ask how she knew that, but at this point I just go along with what she says.

We get out of the car. As we walk to the bar we get some whistles from of few guys hanging outside. We go inside. The bar looks a little sleazy, guys outnumber girls about 3 to 1. Ashley is clearly the hottest looking woman in the bar. She finds a small table in the corner and we sit down. Ashley tells me how good I look. "Follow my lead and we will get some free drinks."

It doesn't take long before two men offer to buy us drinks. They are both good looking and I would guess about 30 years old. When they come back with the drinks they sit with us and introduce themselves as Derek and Matthew. After a few minutes Derek puts his arm around Ashley while Matthew has his hand on my stocking covered legs. Ashley and Derek make out for a few seconds when she stops him and says, "Brianna and I need to go to the ladies room."

"These guys are kind of hot. If you are nervous we can just leave, or we can stay and see where the night takes us."

To be continued.