Winning the Blonde Goddess Ch. 02

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Darya takes Scott's anal virginity.
7.4k words
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Part 2 of the 8 part series

Updated 06/08/2023
Created 01/08/2018
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Fairhaven is a very multicultural city. Even the most casual of observers will notice that we have a considerable number of citizens who are of Chinese ancestry here.

If you are somewhat more observant you will also notice that we have a sizable number of people living here who are Honduran, Korean, Nicaraguan, Russian, Salvadoran, Thai and Vietnamese.

I haven't lived in this city for very long, and I'm still trying to get the hang of things. I still have trouble telling the difference between Hondurans and the Nicaraguans. Or the difference between the Thais and the Vietnamese.

Most of the time it doesn't make a difference, however, when a soccer game is being played between the Nicaraguans and the Hondurans do not root for either team until you know the ancestry of the people that surround you. People in Fairhaven take their soccer very seriously, and they can get angry if you root for the wrong team.

I felt sort of like a fish out of water in Fairhaven. I didn't grow up in a very multicultural neighborhood, and I'm still trying to fit in.

I live in Fairhaven now because I was accepted by the Chandler Theater, Fairhaven Center for the Performing Arts, to be one of their performing dancers.

The Chandler Theater is nowhere near as big or famous as the American Ballet Theatre, but once they'd offered me a contract, I had to take it. My parents both performed ballet on stage and they insisted that there was no way that a son of theirs could be anything else in this life other than a professional dancer in the world of ballet.

Am I getting off track here? I feel like I'm getting off track here.

So, I suppose I should start off with my doctor's appointment at the Augustus Beach Medical Group. According to Darya, this is where all the dancers and choreographers with the Chandler Theatre go when we need medical help.

Okay, maybe I should explain about Darya. Darya is another dancer with the Chandler Theatre. She has a face like Jennifer Lawrence and the svelte, graceful, toned body of a ballerina. She also has a sexy Russian accent. I have a huge crush on her and swore that I would do anything to make her my girlfriend.

Darya took my oath seriously, and she's testing the strength of my commitment by forcing me to pass certain tests before she will officially accept me as her boyfriend.

The first test she came up with was rather humiliating, so, I wasn't overly surprised when the second test turned out to be humiliating as well.

For the second test, I was supposed to allow Darya to fuck me with a fake cock. I'm well-hung, however Darya's fake cock was even larger than my real one.

Darya assured me that there was no way my tight, little anus could take being impaled on her massive thermoplastic rubber cock without causing me injury.

"Your tiny, boyish anus will need to be opened and widened," Darya assured me, "This is time-consuming, but not very difficult."

Not difficult.

Okay, that part confused me. If it wasn't very difficult, why did I need to see a doctor to help open and widen my anus? If it was simple why couldn't a simple layperson do it?

I suspected that sending me to the doctor was just one more way Darya had come up with to humiliate and embarrass me. And; while I was probably right about that; I allowed the doctor's name to be a distraction to me.

The doctor's named was Doctor Capiendo, and I spent far too much time pondering if the name Capiendo was Honduran or Nicaraguan or Salvadoran or whatever. It turns out that there were factors other than national origin I should have been concerned about.

When Darya told me to make an appointment with Doctor Capiendo, I had assumed that Doctor Capiendo would be a man somewhere between thirty-five and sixty-five years old age.

It's kind of the way doctors are most often portrayed on television. Just think of Doctor Stephen Franklin, Doctor Gregory House, Doctor Bob Kelso or Doctor Perry Cox.

Because of my assumption that my doctor was going to be a fatherly (or grandfatherly) type, I was totally thrown when Doctor Capiendo turned out to be a very attractive woman in her late twenties.

I still wasn't certain of her national origins, she looked exotic, however she utterly failed to have a foreign accent. I guessed that she was born and raised in California.

She had a very slender waist and very high cheekbones. She also had professionally styled hair and lips like Angelina Jolie.

I can't explain it, but somehow explaining my situation to a young, attractive female made me feel much more uncomfortable than explaining it to a middle-aged man.

Darya probably anticipated that. That's probably why she had me make an appointment with Doctor Capiendo in the first place.

"So, Scott," she said all friendly and receptive, "what brings you in here today?"

I had been very evasive with the medical staff when I made the appointment. I thought that would make it less embarrassing for me. It turns out that my tactics hadn't helped me at all. I felt my face heat up almost burning hot with embarrassment as I began to explain my situation.

"Um, well, I sort of have a sexual partner," I said, feeling my face get hotter with every word that came out of my mouth, "And there's been this talk of us having anal sex. There's, um, a problem, um, as my anus is too small and there might be tearing and bleeding unless we can find a way to, um, widen my sphincter muscle."

I thought I might die from having to admit such a humiliation thing, yet Doctor Capiendo didn't even blink. The way she reacted, you might think that she heard this sort of thing a dozen times a day.

"Not a problem," Doctor Capiendo informed me, "The sphincter muscle actually has the capacity to be stretched and widened far wider than most people realize."

She wrote down something in my medical file and asked, "About how wide is the sexual organ that you need to accept inside your anus?"

I made a circle with my thumb and forefinger to indicate how thick Darya's fake cock was it it's widest point. Doctor Capiendo paid close attention to my response and smiled.

Okay, well the girth of your friend's penis is impressive," she said, "but, it's not impossible to accommodate. We just need to stretch your anal orifice first and get it to open wider."

Then, to make my experience even more humiliating, Doctor Capiendo asked me to strip from the waist down, so she could check my anus and make certain that there wouldn't be any complications in making it wider.

It seemed like an added humiliation, however, I was the one who made the appointment and told the doctor that I wanted to widen my asshole, so I suppose I only had myself to blame. I kicked off my shoes, unzipped the front of my pants and in less than a minute I was naked from the waist down.

Doctor Capiendo then had me lean forward, place my elbows on the examination table and stick my exposed buttocks high up in the air.

I knew what was coming, however, being forewarned didn't make me any less squeamish. Somehow, Doctor Capiendo thrusting her fingers into my rectum felt far more humiliating than Darya thrusting her fingers into my rectum.

First, she snapped on a latex glove and then coated her fingers with something called HR lubricating jelly. I was grateful that she used lubricant, however, I was shocked at how cold it was when her fingers speared my anus.

Doctor Capiendo smeared my asshole with the lubricating jelly and then I felt her finger impale my sensitive anus and probe as deep as it could go. She wiggled it around inside of me, locating nerve endings that I didn't even know that I had. Then she added another finger, stretching my anal opening wider and wider, until it hurt.

It was the most humiliating and uncomfortable experience I had ever had with a medical doctor, however, on some level I also found it to be intimate and arousing. Something about being naked from the waist down and at the mercy of a woman who impaled my most secret orifice with her fingers and left me feeling helpless and at her mercy made me feel aroused. My cock even began to swell and get hard. Of course, I never mentioned any of this to Doctor Capiendo.

"Okay, there's no swelling or obstructions," Doctor Capiendo announced after she removed her fingers from my asshole, "However, you are very tight. I don't advise that you and your partner engage in any sort of anal sex until your sphincter muscle had been opened significantly wider than it is right now."

Then she wrote down the address and phone number of a place on Lockwood Boulevard and told me to go there and purchase an assortment of anal training tools.

"Anal training tools?" I asked.

Doctor Capiendo smiled reassuringly and replied, "They're not that complicated."

Then she went on to explain, "Basically, they're items that are made from plastic that are designed to be inserted into the rectum for sexual pleasure. In some ways, they're like a dildo, but they tend to be shorter, and have a flanged end to prevent the device from being lost inside the rectum. The smallest ones will be only slightly thicker than my finger. The thickest ones will be about as thick as your boyfriend's penis. You start off by inserting one of the smaller ones into your rectum and then you keep it inside of you most of the day for two or three weeks. Having it constantly inside of you will keep your sphincter muscle from closing up, thus it will be forced to remain open and become wider."

I was about to ask the obvious question of what to do next, but the good doctor answered that question before I could ask it.

"And then you move up to the next larger size," she continued, "If you keep one of these inside your rectum religiously and keep transitioning up to the larger size every few weeks, you should be able to enlarge your sphincter muscle safety and eventually be able to have anal sex without hurting yourself."

. . .

It was embarrassing having to tell Doctor Capiendo that I wanted to widen my sphincter muscle for the purpose of having anal sex, and it just got worse when I had to go to the sex shop on Lockwood Avenue.

I had never been inside of a sex shop before, so I didn't really know what to expect. I stepped inside and wandered around, gawking at everything like a tourist. I think I got a sense of what Alice felt like when she wandered into the Mad Hatter's Tea Party.

Before I set foot inside of the Pleasure Palace, I had never even heard of some of the things they sell there.

I wandered up and down the aisles of the store, wide-eyed as I discovered for the first time the existence of Ben-Wa balls (also marketed as Kegel balls) bullet vibrators, clit cylinders, clover clamps, cock rings, double-headed dildos, fleshlights, menthol nipple balms and panty vibrators.

I vastly expanded my vocabulary of sex-products and got some idea of what they were used for, however, I couldn't seem to locate the anal training tools that Doctor Capiendo had advised me to purchase.

I was about to walk out of the store and call Darya and explain that my attempts to become her anal bitch were running into some serious obstacles, when one of the store employees approached me.

A young man in a black T-shirt with the Pleasure Palace's store logo walked over to me, his mouth split open in a non-threatening, inviting smile. The name Manny was engraved on his shirt, above the store logo.

Manny was young, slender and had long, wavy hair that had a habit of getting into his eyes, although the way his hair was cut and styled I got the impression that it was supposed to get into his eyes. I got the impression that there was a look he was going for, sort of like the actor who played William Scully on the X-Files.

What is it with me? I can remember every step of a pas de deux with extremely detailed choreography, however I can't remember the names of any of the actors that I've seen on television.

"Could I assist you finding something, Sir?" Manny asked me.

I was hoping to sneak into the Pleasure Palace and sneak out without attracting any attention to myself, however, Manny had already screwed up that plan, so, I figured there was no harm in asking for his help at this point.

"Maybe you can," I confessed to Manny, "I was looking to purchase an assortment of anal training tools, but I can't seem to find them anywhere in the store."

The words sounded strange coming out of my mouth, but Manny didn't seem to think my words were odd at all. As a matter of fact, he seemed to understand exactly what I was looking for,

"We have those, you're just in the wrong part of the store," Manny informed me, his friendly smile never wavering, "The front of the store is set up mostly for straight men and heterosexual couples. Then the products for lesbians are on the aisles further back. The products for gay men are in an area of the store that's kind of hidden."

Manny was polite and trying very hard to be helpful, however I felt insulted and embarrassed at the way that he implied that I was gay, and I could feel my face flush hot.

I followed him into an area of the store that was partially obscured by a beaded curtain (and from a distance the beaded curtain looked more like a large rainbow flag than a curtain hanging in a doorway), and soon found myself surrounded by even more products that I had been previously unaware of.

There were Stay-erect delay creams that would allegedly keep a man's cock hard for extraordinary time periods. There were also cock-and-ball straps, penis cages, vibrating urethral sounds and stainless-steel prostate stimulating electrodes.

Manny eventually led me to an aisle where he said they sold the products that I wanted. There wasn't anything in the aisle labeled as an anal training kit, however, Manny assured me that the name of the product wasn't as important as the design and effectiveness of the product.

Manny picked up several cardboard boxes with clear plastic windows, with products inside that were labeled as butt plugs. Doctor Capiendo never used the phrase "butt plug" in her discussion with me, however the shape and size of the butt plug seemed to match her description of what I needed.

"I get lots of twinks in here, buying these," Manny explained, "I've worked here for about two years now, and I must have sold these to more than a hundred customers that needed help in enlarging the entrance to their backdoor. I understand what twinks need to stay safe and keep from being injured during anal play."

"Twinks?" I asked. Manny and the store he worked for, seemed to have a completely different vocabulary from the one I was used to. I was tempted to ask if there was a dictionary I could buy that would explain all of these new terms to me.

"Twinks," Manny reiterated, "It's a word mostly used in the gay community, but I've heard a few heteros use it too. It refers to young, smooth, slender, boyish men, just think of the men you see doing professional figure skating."

"Or male ballet dancers?" I asked, realizing that Manny had just described every single male dancer with the Chandler Theatre. We were all young, slender, smooth and boyish-looking. Apparently, Christopher, Nari and all my fellow male ballet dancers were twinks. I wondered if I should inform them of their status. Would they be pleased to know that they were twinks?

"Oh yes," Manny enthused, "Have you ever seen Julian MacKay perform in skintight spandex? He is delicious! Oh my God, I envy whoever it is backstage, that helps him peel that uniform off after the show is over."

For once we were on familiar ground. I knew who Julian MacKay was. Like me, had was born into a ballet family. Unlike me, he had become world famous for his successes. In 2016, MacKay became the youngest-ever soloist at the Mikhailovsky Ballet in St. Petersburg. He was something of a celebrity in the world of ballet.

Although, I had never heard him referred to as a twink before, or as delicious.

"I've seen him perform before," I replied without the same libidinous enthusiasm Manny was exhibiting, "He's kind of famous in the world of ballet."

Manny raised one inquisitive eyebrow, looked me up and down and inquired, "You're not a ballet dancer, are you?"

"Actually, I am," I replied, "I just recently signed a contract to dance for the Chandler Theatre."

"That is incredible," Manny gushed, "I've never bought tickets to one of their performances, but I might buy one now just to watch you perform! I'd love to see you on stage!"

Manny proceeded to make small talk and ask me about rehearsals, social relationships with other dancers, stage fright and performing in front of audiences of thousands of people. I wasn't certain if he was really interested, or if he was just trying to make me feel more comfortable and hoping that I'd spend more money if I felt more relaxed and at ease around him.

In the end, I don't think it made much of a difference. I basically bought the items that I had come in to buy.

"These come in six sizes," Manny explained about the butt plugs, "extra-small, small, medium, large, extra-large and Oh My God! Is that thing really inside of me?"

Manny was joking. The largest size they had was labeled as XX-Large, however Manny was trying to inject humor into his sales pitch. I didn't laugh at his little joke, but he did earn an amused smile from me with his attempt at humor.

I decided to purchase one of the small butt plugs to start off with, also a medium-sized plug, a large plug, an X-large and an XX-large.

I'm not really sure why I bought the XX-large butt plug. That seemed like overkill. Once I could comfortably take the X-large plug into my anus, I was certain that I'd be ready for Darya, but I bought the insanely large one anyway.

Manny also talked me into purchasing a container of lubricant, that he insisted was essential for inserting the butt plugs into my ass.

"This lubricant contains Jojoba," Manny explained, "It's this really great oil with medicinal properties that helps the sphincter to relax without numbing the ass. I've used it before, and I highly recommend it."

Manny talked me into buying five anal plugs, the anal lubricant and a shower enema system. I ended up spending over two-hundred dollars by the time I was finished, and Manny seemed to have become my new best friend.

. . .

The first time I ever inserted an anal plug up my anus, it felt awkward and foreign, however I quickly adapted.

I also quickly learned that the anal plug was almost entirely concealed once I had it positioned properly inside of me. Even if I were fully naked, the plug was almost impossible to see. I've basically have to bend over and spread my buttocks apart before it became noticeable.

I had an anal plug inside of me every day during ballet rehearsals and none of my fellow dancers had any clue, despite the fact that I was wearing spandex tights that perfectly showcased the shape of my ass and rode up into the tight furrow between my buttocks. I could feel the anal plug inside of me and was aware of its presence most of the day, however, nobody else was aware of it burrowing deep inside of me.

Certain dance positions and stretches made me far more aware of the plug than others, however, no matter what the plug did, or how it moved inside of me, nobody in rehearsals could see it.

About once a week, Darya would check up on me and inquire about my progress in widening my sphincter muscle. Her icy-cold disposition was melting somewhat, and it seemed that she was getting eager to have me naked and bent over so she could violate my tight, sensitive anus.

One evening, I was in her apartment and she grabbed my butt cheeks with both hands and squeezed my butt enthusiastically and said, "Do not make we wait much longer, Scott. I see these beautiful buttocks every day in rehearsals, and every day I cannot possess them, it feels like you are teasing me."