tagAnalGiving It Up For Success

Giving It Up For Success



Amy Porter had just finished reading a script sent by her agent. He was right there was a part in the movie that was perfect for her. It wasn't a starring role but definitely a bigger role than she had had in previous movies. This could be her big chance but there was one hurdle to overcome, the casting director for the movie.

She was devastated that the director had selected Sydney Hastings as the casting director. Sydney was a pervert and addicted to anal sex. It was because Amy had refused to give up her ass to him that she was never cast in any of his movies. He had made it very clear. All she had to do was lean over his desk and drop her panties. If he got to fuck her ass, she was in the movie. Amy knew that many an aspiring actress had done just that.

Amy was a pretty woman at age 28 and an up and comer in the movies. She thought about calling the director and telling him about her dilemma but dismissed it quickly. She knew that only the leading roles got to bypass the casting director. She swung her legs out from under her and raised her 5'7" frame to her feet. Walking to the bar to get a glass of wine she wondered why Sydney wouldn't be just as content if she fucked him or a blow job.

She poured the wine an ambled back to her sofa stopping to check out her figure in the wall mirror. Amy liked what she saw in her 34-28-35 figure. She had firm breasts, shapely legs and a very nice bottom. Even though her ass was appealing, none of the guys she dated ever went for it. She had never had anal sex and had not planned to ever. However now she was challenged. Did she go for the role of her lifetime or hang on to her anal virginity?

Sitting back in the sofa sipping her wine a thought came to mind. She would call another actress Brooke Jensen. Brooke had one of those asses that guys could not leave alone. It was big, round and perfectly shaped. Brooke was known to engage in anal sex and had even become fond of it. Brookes would know what to tell her and if she decided to give up her ass for the part, Brooke would be able to give her some tips on preparing for anal sex.


Amy called Brooke and explained her situation.

"I can certainly help you out. Come on over to my place and we can talk it through. If you decided to go through with it, I will help you." Brooke offered.

"Is tomorrow too soon?"

"No, tomorrow is fine. I am reading a script as well and your visit will be a pleasant break from it."

"Great, I will see you tomorrow and thank you."

Amy went to bed somewhat relieved after talking to Brooke but she was still nervous about the decision. She had a restless night's sleep and she was glad the next day when it was time to go to Brooke's place. Amy arrived at Brooke's and they greeted each other with the customary kiss on both cheeks. Brooke brought Amy into the living room and served coffee.

"It's too bad that Sydney got the casting job for this movie. It does put you in quite a spot," Brooke began.

"It's dreadful. This role is so right for me and could be the start of bigger things to come."

"That's what you have to think about. Is it worth protecting that cute ass of yours versus the role of a lifetime?"

"I know. I'm so confused. I don't know what to do. That's why I needed to see you."

"Amy, nearly every actress who came up the way we had to has had anal sex along the way. The good thing with Sydney is that once he has you he moves on to the next girl."

"So it would be a onetime thing with him?"

"Definitely and the other thing is that he is not at all well-endowed. In fact he has a small prick. He can't get off fucking a pussy because it's not tight enough for him."

"Why not oral then?"

"He is fascinated with the female bottom. It's the only thing that satisfies him."

"You've done anal haven't you?"

"Of course, many times and I still do."

"Do you like it?"

"I've learned to like it. The best is when the guy cums in my ass. I love that sensation."

"Is it like an enema?"

Brooke laughed and replied, "I guess you could say that but it has never caused me to poop. I will say when I first had anal sex that I felt very constipated afterward. However, that's not the case anymore."

"When was your first time?"

"It was right after college when I started in this business. We were having a rehearsal that went late and two guys offered to take me home. I have to admit I was wearing very tight jeans and my ass was accentuated."

"Your ass is always accentuated. I have never seen another that is so round and so perfectly shaped."

"Well it got me in trouble that night. At first we sat in their van and had a few drinks. We started getting amorous and the next thing I knew I was in the back of the van sucking this one guy's cock. The other guy unfastened my jeans and with some difficulty pulled them down just below my buttocks. I felt his cock enter my pussy from behind and I was enjoying my first threesome."

"So you gave up your ass in their van?"

"I didn't exactly give it up. The guy fucking me from behind started caressing my ass and it felt good. He tickled my anus and I liked that too. The next thing I felt was a tube entering my ass and flooding it with some sort of lubricant. The guy kept fucking me but started fingering my ass with his fingers. Before I knew it, his cock entered my ass but he was gentle and let me adjust to him. I was shocked but I let him have his way as it really didn't hurt that much. He kept feeding it to me until he was buried in my ass."

"You mean it didn't hurt at all?"

"No, at least not excruciating pain which is what I expected. There was some discomfort at first and then a bloating feeling but eventually I just felt the fullness. He kept fucking me until he came and he flooded my rectum with his seed. I had never felt so full. Surprisingly my sphincter seemed to have a mind of its own and it massaged his shaft. He pulled out of me and then the guy I was sucking moved behind me and fucked my ass."

"Oh wow, you make this sound very hot."

"The second guys came quickly and dumped another big load in my rectum. They left me on the floor of the van and drove away. I still had my jeans down around my knees when we arrived at their place. They brought me inside and they both fucked my ass again before they crashed. They put me in one of their beds. I felt so full I had to douche my bottom so I went to their bathroom and did the best I could."

"Did you make it home the next day?"

"No they kept me at their place all weekend and fucked me continuously on Saturday and Sunday. I always had a cock in my ass and the other one either in my pussy or my mouth. The guys were young and virile and could cum four times a day. I was absolutely drained when they took me home on Sunday evening."

"I'm surprised that you could even walk."

I was surprised too but they had really broken in my ass and I had actually started to like the double penetration."

"You still do anal right?"

"Yes, but I am very selective. I have let a few producers and directors do me because it helped my career. If I like a guy who is into anal, I will usually do it but only if he takes good care of my pussy."

"God, listening to you makes my sex life sound like child's play."

"So what have you decided to do? Have I helped at all? Where do you want to go from here?"

"I think that I am going to do it. This part is too important to pass up."

"So have you ever had anything in your ass?"

"I have never had anything in my ass other than my finger," Amy admitted

"So do you want my help to get ready for Sydney?"

"Yes, I do but I'm scared."

"Well we will have to take it slow and gradually introduce bigger things into your ass. Trust me I will guide you and make sure that you are not hurt. I know just the thing to get started. Come with me and we will first douche your bottom."

Amy followed Brooke into her bedroom where Brooke told her to remove her clothes. Amy was surprised when Brooke disrobed too. Brooke took Amy into the bathroom where she douched Amy's bottom getting it very clean. Brooke noticed Amy trembled a little and that goose bumps appeared on her body. Brooke took that as a sign of encouragement so she had Amy bend over the bathroom tub as she knelt behind Amy and began to tongue her nether hole. Brooke got Amy's asshole wet with her tongue and then inserted a saliva moistened finger into the opening of her ass. Brooke pressed her finger in Amy's sphincter and let it slide in up to the knuckle causing Amy to flinch and groan. Brooke removed her finger and then she spat into Amy's ass allowing her saliva to moisten her further. Brooke dipped her tongue back into Amy's bung hole and Amy almost orgasmed with the eroticism of the moment. Brooke alternated between eating Amy's ass and finger fucking it. Brooke's fingers now slid easily in and out of Amy's hot asshole.

"Come to bed," Brooke ordered.

Amy went back into the bedroom and Brooke had her get on the bed on all fours with her beautiful ass pointed in the air. Brooke told Amy she would be right back and she left the room. Brooke returned shortly carrying a jar of lube and a string of beads. Brooke applied the lubricant to Amy's asshole and Amy felt the soothing cool lube coat her rectum. Brooke began to insert the anal beads into Amy's ass one at a time. Amy unable to talk, allowed Brooke to have her way with her. One by one Brooke pushed the beads into Amy's ass until all six of them were buried in her rectum.

"Are you okay, any pain? Brooke asked.

Amy nodded that she was okay and that there was no pain. Amy only felt the fullness in her ass from the anal beads as they were clearly thicker than any finger and they were deeper than anything else had ever been. Brooke massaged Amy's beautiful ass cheeks and reached between Amy's legs to diddle her clit. Amy felt herself getting hot and she felt the onslaught of an orgasm. She had never had a woman touch her like this and it was strange but exciting.

Brooke sensed it too and she rolled Amy over on her back. Brooke then got between Amy's legs and placed her mouth on Amy's pussy. Brooke placed Amy's thighs on her shoulders giving her complete access to Amy's twat. Brooke ate Amy with a passion and she felt Amy start to tense as her orgasm built within her. Amy groaned as she tightened her thighs around Brooke's neck as the first wave rocked her body. As Amy began to cum, Brooke pulled gently on the anal beads so that they popped out of Amy's ass one at a time.

Amy had never felt anything like it and she seemed to cum as each bead cleared her asshole. Her body went into spasm and jerked like never before. She was overcome with the lust of the moment as it seemed she would cum forever. Brooke kept her mouth glued to Amy's pussy throughout her orgasms and sucked every drop of Amy's nectar into her mouth. Amy finally collapsed on the bed her body spent and incapable of any more movement. The sensation in Amy's ass felt as if the anal beads were still in her but she knew Brooke had pulled them out of her hole.

"I have never cum like that in my life," Amy said, finally able to talk and then added, "That was two firsts for me, having something in my ass and a woman eating my pussy."

"I hope you liked it."

"What's not to like?"

Next Brooke got behind Amy and began to caress Amy's lovely curvy ass. Brooke was enamored with Amy's shapely bottom and she planted light kisses on Amy's ass cheeks. Amy cooed as Brooke worked her ass. Brooke began to finger Amy's asshole with first one then two fingers. The fingers felt snug but both Brooke and Amy knew that Amy's ass was beginning to loosen up. Brooke removed her fingers and then she placed something at the entrance to Amy's ass.

"This will be a little bigger than the beads and it will stay in you easier than a regular dildo. It's called a butt plug," Brooke cautioned Amy.

Brooke then inserted the head on the butt plug into Amy's ass. Once it cleared Amy's sphincter it settled in her ass and Brooke left it there. Brooke then put on a strap-on dildo and put it in Amy's pussy. Amy had never been as full in her life as she did now with the two fake members in her.

Amy cried out to Brooke, "Let me turn over," she pleaded.

Amy rolled over onto her back and Brooke pushed the fake cock back into Amy's pussy. Brooke picked up the pace fucking Amy's pussy. Amy could feel the dildo in her pussy rubbing against the butt plug in her ass and she then realized what it must feel like to be fucked by two cocks at once. Amy was going wild and suddenly wished that she had another cock in her mouth. She had never been so turned on as she was at that moment.

Amy could feel another orgasm building within her as Brooke pounded her pussy with her fake cock. Brooke was panting as the nub on the dildo rubbed against her clit and she too was close to cumming. The two beauties frantically humped their bodies at each other and then they both exploded with an intense orgasm. Brooke collapsed on top of Amy and their breasts were crushed together. Brooke reached under Amy and pulled the butt plug out of Amy's ass. Amy's body jerked with another spasm as the plug left her asshole with a loud pop.

"Oh my God, you are going to wear me out. I have never cum so much and so often," Amy confessed and then she requested, "Can we rest awhile?"

Brooke opened the bottle of lube and Amy felt a blob of it fall between her ass cheeks. Amy's ass was still tender from her episodes with the anal beads and the butt plug but the lubricant was soothing as Brooke coated Amy's tight ass.

"Please don't hurt me," Amy pleaded.

"Don't worry I will go very easy, just relax," Brooke assured her.

Amy soon felt the head of the fake cock press against the opening of her tender asshole. The head of Brooke's rubber cock was slick with lubricant and it slid in easily into the stretched opening of Amy's ass. With one push Brooke pushed the cock past Amy's sphincter and it rushed deep into her ass taking Amy's breath away. Brooke obviously loved the sensation of screwing Amy's ass and Amy wiggled it as Brooke thrust into her while playfully slapping Amy's ass cheeks. Amy moaned deeply with the thrust of the fake cock and her cries filled the bedroom.

Minutes later Amy and Brooke had showered, dressed and were sitting in the living room. Brooke served white wine and they relaxed from their intense sexual activities. Amy sipped the wine and spoke. "I felt as if I should have reciprocated somehow."

"Another time and besides, I have a date Sandyght so I will be well taken care of."

"This really helped me but I am still a little nervous about Sydney."

"Don't worry about him, you'll be fine. Take the anal beads, butt plus and slim dildo with you today. You can continue to work on your ass at home."

Amy blushed but thanked Brooke. They finished their wine and Brooke put the sex toys in a bag for Amy. They said goodbye with kisses on both cheeks and Amy drove home. It had been quite an afternoon and one she would not soon forget. When she got home she soaked the sex toys in her sink as Brooke had instructed so that they would be clean when she wanted to use them. Amy poured a glass of wine for herself and thought about Monday when she would call Sydney. She had all day Sunday to use the toys and prepare for her meeting with the casting director. Amy drank watched some no brainer movie and killed the bottle of wine. She fell asleep in her sofa with the TV on. Early in the morning she awoke, turned the TV off and went to her bedroom where she slept until late Sunday morning.


Amy woke up Sunday morning, made coffee and decided to take a warm bath. She felt slightly constipated but she knew it was because her sphincter had been stretched somewhat. It really didn't feel that much different from when she passed a large stool. She added bath beads as the tub filled and as an afterthought she retrieved the sex toys that Brooke had loaned her. Amy eased her shapely body into the warm slick water and reclined with her cup of coffee. She had chosen her travel cup because it held more coffee and it wouldn't spill into the bath water.

The oily water felt good on her body and she ran her hands over her breasts and teased her nipples. She was turning herself on and she began to finger her pussy. Then she remembered the toys and decided to have some fun in the tub. The water made the anal beads very slick and Amy eased the five beads in one by one. The string floated between her legs.

Next she took the dildo and eased it into her pussy. It was a slim one which Brooke had told her was about as thick as Sydney's cock. Amy maneuvered the dildo around in her pussy and ran the head over her stiff clit. She could feel an orgasm building within her and as she got close she pulled the anal beads out slowly. Her body jerked as each bead cleared her anus and she cried out in ecstasy. The beads served to intensify her orgasm and then she released the beads and the dildo.

Amy sighed and reached for her coffee as the toys floated around in the tub. She thought to herself, "I could get used to these toys."

She remained in the tub until she finished her coffee. She got out of the tub, dried off and put on a bath robe over her naked body. Amy recalled that Brooke suggested that she walk around the house with the butt plug in her bottom. Amy decided that she would do that after breakfast. She drained the tub, dried off the toys and went to her kitchen to make a light breakfast. Following breakfast she sat in her living room and read the script again but only the part that she hoped to get.

Her mind drifted to Sydney again and she knew what was in store her next week. Amy decided to put the butt plug in her ass and leave it in as she read through the movie script. She found that after time had passed that she had become accustomed to the increased pressure. The presence of the butt plug made her horny again and she played with her pussy and clit until she climaxed a second time.

Amy removed the plug and washed and dried it. She threw on her sweats and went outside to retrieve her Sunday newspaper. She had no plans that day so she was content to read the paper, reread the movie script and watch some TV. That evening she made pasta for dinner and opened a bottle of red wine. She was careful not to have more than two glasses. That night she went to bed and was somewhat restless as she was nervous about Monday. Eventually she dozed off ad slept peacefully.


Amy called Sydney first thing Monday morning and she was told in no uncertain terms not to waste his time. She explained that she was willing to do what it took to get the part and he was thrilled. He told her to be at his office at 2:00 PM that afternoon. Amy still struggled with the thought of giving up her ass to such a pervert but she knew she had no choice if she wanted the part. She wore a light weight sweater and a pleated mini skirt. She passed on any hose as she did not need them. Her legs were well tanned and looked great. When she arrived Sydney was pleased to see her.

"So you finally decided to come around did you?" he asked with a sneer.

She found the short, chubby balding man to be repulsive but she managed a s mile and replied. "I think that this part is perfect for me and I want it badly."

"Good, I agree it is perfect for you. Now come over her and stand by my desk."

Amy moved painstakingly toward him and he smiled sensing her dilemma. "That's it don't be shy. Now place your hands on the desk and lean forward. That's it very nice."

She placed her hands on the desk and leaned over waiting for the next move. Sydney stood behind her and lifted her skirt up and draped it over her back. He stared at her lovely panty clad bottom and remarked. "You have a beautiful ass and I am going to enjoy fucking it."

Report Story

bywalterio© 0 comments/ 81294 views/ 48 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: