It Was So Intense That I Almost Blacked Out

When I came out of the secure area at the airport, Taylor ran screaming toward me and we embraced, and I started crying. It had only been two months since she’d left our hometown to attend college, but we’d known each other for years, and I missed her.  She kissed me on the forehead and said, “Stop that, you’re here now.”

Taylor was a good friend of mine and had moved to the west coast to go to school and to work for a modeling agency that had offered her a contract.  Even though she was the same age my sister was, we’d connected and gotten closer since we’d moved to the Nashville area a few years prior.  The day she left, I’d cried like a baby, and my parents had promised to let me fly out to see her for my 16th birthday.

“Tell me what the surprise is.”

She just laughed and said it would have to wait. She’d hinted to me before I left home that she had some huge surprise she needed to share with me, and I was anxious to find out what it was.

With Taylor were two incredibly gorgeous girls that appeared to be about the same age as she was. She introduced them to me as her roommates, Tawny and Angel. I commented on how incredibly pretty they were, and they both reciprocated with statements about me being as pretty as my friend was.

On the ride to Taylor’s apartment, I couldn’t believe how massive the city was, and how much traffic there was. I had often complained about the traffic in Nashville, but it was nothing compared to this – in places there were seven lanes of traffic, all bumper-to-bumper. I was flabbergasted at how many cars there seemed to be, all lined up in one big, long, slowly-moving parking lot.

When we got to her apartment, I was amazed at how ornate the grounds were and how extremely well-kept the buildings looked. I surmised to myself that these apartments must cost a fortune to live in, and was impressed with the fact that Taylor was making enough money to live like this!  The interior of the apartment was no less impressive, and was furnished with an eloquent collection of furniture.  The only thing I could muster at the time was , “Wow!”

I put my bag in Taylor’s huge room, and she gave me the grand tour of the place. It had an awesome array of appliances – top of the line stuff as best I could tell.  It had a security system, 120-channel cable television, ¹ three phone lines, high-speed Internet service, a huge balcony, and space out the ass. “How much does all of this cost?” I asked.

“About $2,500 a month,” she said.

My jaw hit the floor. “How in the fuck do you pay for this?”

“Wellllllll,” she hesitated. “I work. That’s what I wanted to talk to you about.”

“Okay, well talk. I’m all ears.”

“I’m an actress. I make movies.”

“Seriously? What have you been in? Anything I have seen?”

“I hope not,” she laughed.

“I don’t understand.”

Taylor hesitated, “You know that I wouldn’t do anything to let myself be hurt, right?”

“Sure, I guess,” I replied, a wave of confusion washing over me all of the sudden.

“Well, the movies I make are, how do I say it, not what you would see in a regular movie theater,” she chuckled.

I hesitated for a second, trying to decode what she meant, when it hit me like a ton of bricks, “You’re not making fuck movies?” My jaw dropped again.

“I prefer to call them ‘adult entertainment’ movies.”

“Oh, my god, why?” I cried out.

“Why not,” she asked, “What’s really wrong with it? It’s just having sex, but being filmed while doing it.”

“I know, but still, making pornos is so…..” I wasn’t sure what to say.

“Disgusting?” she asked.

“No, that wasn’t what I was going to say. I’m not sure what I was going to call it. It just caught me off guard, that’s all. Do you make good money doing it?” I asked.

“Just look around you, babe. All of this is being paid for with that money. You should know that Tawny and Angel also work in the industry; all three of us do.”

“Holy shit!  I don’t believe this. Oh my god. What happened to the poor innocent little Taylor that left me just two months ago?” I said, feigning concern. Secretly, I was thinking to myself, “I wonder what it is like to fuck while people were watching you?”

She just laughed, “I promise you, she’s still here, Alexa. Please know that – I have not changed in any way, other than the work I do.”

“How in the hell did you get into making fuck movies?” I had to know.

Taylor spent the rest of the evening over dinner explaining to me about how a girl she knew who’d worked for her modeling agency had done some porn work, and had basically talked her into trying it at least once to see how it went; she wanted to see if it would be something that would interest her.  She’d gotten tested for diseases, signed a release, and spent the majority of one day doing sex scenes on film with some “guy with a huge dick.”  She walked away with a pretty good sum of money for a few minutes worth of work.

I know Taylor and she loved the physical aspects of sex just as much as I did, maybe even more. So it came as no surprise to me that she had enjoyed it, though she indicated that having to stop and adjust angles for the cameras got to be tiresome much of the time. She went on to tell me that one of the major adult movie production companies had taken a serious liking to her and thought she had the kind of look they wanted to see, so they offered her a one year, exclusive contract after she’d done two more video test shoots to confirm that she had the moxie to actually fuck in front of the camera.

“What all have you done? I mean, like, sexually. Have you done anal?” I had to ask.  I’d become intensely infatuated with the concept of anal sex of late.

“Yeah, I’ve been butt fucked, I’ve done lesbian shoots, I’ve even done DPs,” she replied

“What’s a DP?”

“A DP is a double penetration – one dick in your pussy and one in your ass at the same time. That’s an incredible feeling.”

“Fuck me! Jesus, Taylor.” I said with a wide-eyed shock on my face. “Did the anal hurt?”

“No, I practiced before I did it so it didn’t hurt at all, actually.”

“You practiced?” I laughed.

“Yes, I practiced. What the fuck? Don’t you know anything, bitch?”

“Well, I didn’t know you could practice for something like that,” not realizing that the way I lost my hymen was, in fact, “practicing” in this sense of the word. ²

“Yeah, basically you just play with your asshole, and stick fingers or dildos in it to get it used to being penetrated. Once you do that for a while, it gets used to it, so when the cock gets ready to go in, your ass is not all tensed up and stuff. It works.  Really.”

“Damn, I’ve wanted to do anal for a while now, but I’ve always been scared to death it is going to hurt, so I’ve just never done it.”

“Well, you’re in the right place to learn,” Taylor laughed.

I wasn’t sure if she was being serious or not, but I jumped at the chance to find out, no matter how remote the possibilities might be. “You want to teach me?”

“Oh, wow, that would seem….weird if *I* taught you how to do anything, don’t you think?

“Well, just tell me what I need to do to “practice” and we’ll go from there.”

“What do you mean, ‘go from there?’” she inquired.

“I don’t know – surely I can find someone with a dick that would like to do a girl in the ass, don’t you think?” kind of half joking, but really not.

“Oh my god, are you fucking serious?” she laughed.

“Hell, yeah. If you know all of this stuff, teach me some of it, dammit!” I smiled with one of those troublemaker smiles I was famous for.

That night, Taylor and her two friends and I sat down and they explained to me how to practice for anal sex – how to prepare to be penetrated anally without it being painful. When the subject came up of someone that could or would actually want to “break me in” as Tawny put it, they floated around a couple of guys names that they thought might be willing to lend us a hand. They settled on one guy whom they said had a nine inch dick. They figured if I was going to lose my anal virginity, I might as well do it in grand style.  Since I’d only had one dick in me, I was sorely lacking when it came to understanding the true concept of “penis sizes.”  The gravity of such a discussion was lost on me at the time.

They called this guy early the next morning, and apparently it took little convincing for him to accept the task of deflowering a 16 year old girl’s asshole. Now that I think about it, I would have loved to have seen the look on his face when they first asked him if he’d be willing to help out. He was to be at the apartment the following Friday. In the meantime, I had some practicing to do.

The “practice” for my first anal was basically a series of masturbatory penetrations of my own asshole with first one finger, then two, then three, and then progression on to a couple of dildos Taylor let me borrow. The idea was to get my hole used to having something in it, and to get a sense of how the lower half of my body would react to the intrusion, and teaching it how it should react. I was given a HUGE jar (industrial size?) of KY jelly and told to spend some spare time “practicing” on my own, and to let the girls know when I had gotten the large of the two dildos in my butt with little problem.

Of course, I had played with my asshole in the shower and while masturbating before, but I had never seriously penetrated it with anything. I masturbated for a few minutes to get myself in the mindset to be butt fucked, and to make myself wet. Finally, I was ready to take that next step. As I lubed up my finger and pressed against my tight little rosebud, I sensed the pushback and clenching that they’d told me I would. Nevertheless, I slowly pushed my finger into my asshole and thought to myself, “This is incredibly tight.”

As I moved it in and out, I fantasized about having a huge dick pounding away at my butt. I could already feel an orgasm building, even without touching my clit. I wasn’t sure if that was normal, but I didn’t fight the feeling. I reached down with my other hand and masturbated myself while I was finger-fucking my asshole and had a very intense orgasm. After I came down, I withdrew my finger from my butt and looked at it.  There was nothing out of the ordinary on it, thankfully.  I had been concerned that there’d be, well, stuff on it when I pulled it out.

I figured I might as well press on, so I lubed up two fingers and started to insert them in my ass. Again, they went in with relative ease, though my asshole did feel some discomfort while being held open. I began gently fucking my ass with my fingers and continued for a few minutes, at which point I decided to stop and clean up. I’d had as much stimulation as I could handle for one evening, and I had three more to go before the big night. At breakfast the next day, I reported my accomplishment, and thought to myself, “How many people could actually talk about this while eating breakfast?”

As the week progressed, I continued practicing, and had finally reached the point where I was ready to try penetration with a dildo – in this case one that looked remarkably….lifelike. I sequestered myself in my bathroom, and lubed up a couple of my fingers – I had reached the point where I could immediately take two fingers without requiring an initial penetration with a single digit. I had also passed the point where simple penetration of my ass caused me to feel like I needed to orgasm immediately – a feat that I wasn’t overwhelmingly comfortable with – I loved orgasms.

I withdrew my fingers and reached for the rubbery, terra cotta-colored penis substitute.  I spent some time applying a copious amount of KY to it, then reached around and applied more KY to my already anxious asshole. I spent a few seconds trying to determine the correct logistical procedure for inserting this huge thing into my back end, and when I had satisfied myself that I had some concept of what I was doing, I moved my new friend around to my behind. As I began to attempt to penetrate my asshole, I could feel it tighten up considerably, though I was sure it was primarily due to the tinge of the cold KY on the tip of this penile object.

I began to push the dildo into my butt, and after correcting some slippage issues, it passed through the first ring, then past the inner ring. The feeling was incredible to say the least. It didn’t hurt at all, but rather gave me a feeling best characterized as a fullness. I began slowly fucking my ass with this cold, lifeless piece of equipment, and though it felt awesome to be penetrated finally, I couldn’t help but hope that there would be more “feeling” to it when it came time to take a real penis there. Regardless, I spent the following two days practicing with the toys I had available to me and by the time Friday night rolled around, I was confident I would be able to handle whatever, whoever, came my way.

Taylor also explained that, when it came time to do it, I’d need to use an enema to prepare myself, because the guy that would be helping me was quite long and if I didn’t, I might have some “issues.” My eyes widened substantially as I asked why that was necessary. I’d only had one enema in my life that I recalled and that was in preparation for a diagnostic test I had when I was much younger. I don’t remember too much about it, other than being extremely embarrassed by having my back end exposed to some strange guy with a big bag and a tube. I didn’t even remember much about what it felt like. Nonetheless, she explained the process to me and that many of the porn stars use them before an anal scene to prevent problems with fecal matter presenting itself during the act. And, early on Friday afternoon, I gave myself an enema in preparation for what was to come. The feeling was somewhat unique and the whole process was rather awkward.

Shortly thereafter my “stunt penis” arrived.  I was struck by how gorgeous a creature he was. Taylor told me that he was also a porn actor, though he was relatively new to the scene. My first thought was that I was going to get to fuck a real live porn star – even if he hadn’t achieved “star” status at that point. He was very toned and athletic looking, tanned and hairless below the neck – I mentally referred to him as Adonis until I found out that his name was Aaron. When Aaron walked through the door, his gaze caught mine and his mouth opened. He looked at Taylor and asked, “Is this her?” to which she replied in the affirmative. “Oh, man, this is going to be fun,” he said.

I just grinned. “You like taking a girl’s anal virginity?” I asked.

“If she looks like you, I do,” he retorted, “I hope you can handle it.” Ahh, shit.  If there was anything else he could’ve said that would have made me handle it, I don’t know what it would’ve been. I wasn’t about to let this guy get the best of me.

We all spent a little time getting to know each other. Taylor, Aaron, and the other two girls were drinking wine coolers while I was sipping on my diet Coke (since I didn’t drink). I would come to find out that Aaron had done a couple of anal scenes with Taylor, so she was very familiar with his ability to handle his assigned task.

Finally, we decided that it was time for me to lose my anal cherry. Taylor led me into the living room area of their apartment, to a makeshift pallet she’d set up in the middle of the floor. I just stared in amazement and blurted out, “I’m gonna do it right here, in front of y’all?

“Why not?” she asked, “I’ve seen you naked all my life, and everyone here has fucked everyone else, so what difference does it make? Besides, we will help guide you through getting it in and what to do.”

“I think I know what to do once I get it in me, thanks,” I stammered. Taylor won out, however, when she reminded me that she was responsible for me and didn’t want anything to happen to me. I felt as if I were going to be starring in my own porn movie, only without the camera equipment.

I removed my clothes, and took up a position on my hands and knees on the pallet that had been created for my anal deflowering. Taylor suggested that I take the responsibility for getting Aaron’s dick hard. “How am I supposed to do that?” I blurted out unthinkingly.

“Pfft, you have a mouth, don’t you. I know you’ve had a dick in it before. Use your skills, babe.”

Aaron got a huge grin on his face as he assumed a position in front of me, with his semi-engorged penis hanging right in front of my face. His pubic area was completely shaven, something I hadn’t seen before on a guy, so I wasn’t sure if that was what made his cock appear so huge or if it just was huge. I’d been told he was 9 inches long, and it showed, even without him being fully erect.

I took Aaron’s cock in my mouth and hands and within a few seconds he’d achieved maximum hardness. I continued giving him head, however, for a couple of minutes because it had been so long since I had a dick in my mouth, and I wanted to savor the moment. I reached down and played with my pussy while I was sucking and jerking him to make myself wet and to heighten my arousal, as if that were really necessary at that point.

Finally, it came time to have my first real anal experience. Aaron withdrew from my mouth, and asked me if I was ready. I told him with as much confidence as I could muster that I was ready, “Let’s go for it.” He moved around to the back of me and took some KY and dribbled it onto my asshole. I jumped from the coldness (why is that stuff always so cold?), and he laughed. He took his finger and massaged the lube into my asshole, gently at first, but then with increasing intensity. Finally, he penetrated my asshole with his finger to work some of the lubricant inside. I moaned softly and he got the cutest grin on his face as I turned around to have a look at what was going on.

He took out a condom and rolled it onto his cock, and swatted me on the ass with it. “I hope you enjoy this as much as I am going to, little girl.” I felt his dick press at the entrance to my backdoor, and I reminded myself to relax my anus and push out so that his entry would be easier on me. Finally, it happened. Aaron’s cock penetrated the two rings of my asshole in one smooth movement, and he stopped for a second. I grunted.

I would later find out that he was used to having it go in the first muscle, then stopping for a second to let it relax, before proceeding to enter the second ring. With mine, he had pushed the head all the way in, however, and he was concerned that it might have hurt me. I assured him that I was in no pain whatsoever, and that he could continue pushing it the rest of the way in, albeit slowly.

He began lightly thrusting, gradually allowing his cock to penetrate my asshole further, and after a few back and forth thrusts, he had the entire 9 inches buried deep in my ass. The feeling I was experiencing was indescribably intense. I had the incredible sensation of having a full rectum, as if I had to take a huge shit, followed by the sensation of being evacuated as he withdrew. The penetration hadn’t hurt at all, a fact I attributed to all of the practice I had done and mentally said to myself, “It worked.”

“Oh, gosh,” I moaned.

Aaron began actually fucking my ass, not unlike he would’ve done had he been in my pussy, and man did it feel incredible. As he began to speed up, the intensity of these feelings increased. I wanted to reach down and masturbate myself, but I knew it would only take a few seconds before I would achieve my orgasm. I was already on the verge of cumming, and Aaron was not helping by his slow, intense thrusts deep into my anal cavity. I just laid there and let him fuck me in the butt for a few minutes, taking in all of the feelings I was experiencing – the whole lower half of my body felt like it was about to explode.  I was as close to what is known as subspace as I had ever been (and have been since), and had completely lost any connection with Taylor and her friends.  As far as I was concerned, it was just me and him.  He’d grabbed my hips and was full on fucking me by this time.

Finally, it got to the point where I knew I was going to cum whether or not I helped myself out, so I reached back with one hand and began masturbating my clit. It took just ten seconds for that orgasm to begin, and ended up being the singular most intense orgasm I’d had up to that point in my life.  My orgasms were strong to begin with (a fact I attributed to my having been doing Kegel exercises for well over a year at that point), and this one was so intense that I almost blacked out.  I’m sure I screamed and moaned loudly, but I wasn’t paying any attention to that at the time.

My muscular contractions were so incredibly intense that I began to hurt, but it was one of those “good” hurts. My contractions struck a nerve in Aaron as well, and he came as my orgasm subsided. The feeling of a cock spurting in my asshole was likewise incredible. Unlike what I had experienced when a guy was cumming in my pussy, I could feel the contractions of his penis cause my anal muscles to slightly contract and expand, and thought to myself, “This is fucking awesome.” Taylor and the other two girls hooted and hollered and said they were proud of me – they’d never seen anyone take a dick in the ass for the first time and have it go so smoothly.

When I’d returned to Earth, I was suddenly struck by embarrassment over the fact that I had just gotten fucked in front of several other people, one of whom was a good friend. I was still on my orgasmic high, however, and the thought soon escaped me. I don’t remember how long I remained there in the doggy position, but I distinctly remember Aaron withdrawing from my asshole. It was as though a huge suction had been created and left me empty when he pulled out. He made some comment about my gaping asshole and I made a conscious attempt to squeeze it shut, and then just slowly fell forward, flat on the floor, still reeling from my anally-induced high.

“I hope you enjoyed that as much as I did, sweetheart.”

“Fuck, yeah, man. God damn, that was one of the most intense orgasms I’ve ever had.”

“I have that effect on women.”

The girls just laughed in that sarcastic tone that told me that he had a high opinion of himself if he was being serious. As I laid there contemplating what had just transpired, I thought to myself, this is something I will be doing again. I can’t see why anyone wouldn’t want to do this – it feels incredible. I started to get up and realized that I needed to clean my back end off, and asked for a towel. Taylor had thought of everything apparently, and reached over to where she had put a towel just specifically for that purpose. “Welcome to the A-Team, bitch,” she said, “If that didn’t hurt, then you should be able to enjoy anal with just about anyone else you’ll ever encounter.”

“No, no, that felt fucking awesome. Didn’t you just see me cum all over the fucking place?” I asked. I cleaned myself off, got up and went to the bathroom. I felt like I needed to take a huge dump. Once I got in the bathroom, however, nothing would come out. Taylor would later tell me that this was not an uncommon feeling, but that I would get used to it the more I did anal.

The rest of the evening was spent discussing what had transpired that afternoon, and how I felt about it. I certainly enjoyed the experience and knew that I’d be making it a routine part of my sex play from that point forward, but I was now secretly embarrassed that I had done what I had done in front of my own friend. In the final analysis, though, Taylor wasn’t bothered by it. I guess that comes easier to you when you spend a good amount of time fucking in front of a roomful of people to begin with. Angel made a statement about my doing so well that maybe I should become a porn star, to which Taylor shot her a paralysis-inducing glare.

I asked Taylor how she planned to tell her parents about her work. She said she didn’t know and asked if I had any ideas. I couldn’t come up with anything off the top of my head, but promised to let her know if I thought of anything. We both agreed that they’d probably be devastated by the thought of their daughter having sex for money and allowing it to be broadcast for the entire planet to see it. That would turn out to be an underestimation of their reaction, however.

I went to sleep that night extremely proud of myself and realized that I needed to remember to write down the process I used to learn how to take a dick in the ass. I was sure the information would come in handy to others I might encounter in the future (remember, by this point I was already adopting an educational approach to sexuality). I had read questions from many people asking about how to do anal and knew that I’d now be able to supply the information they could use to make their first anal a satisfying experience.

I spent the day Saturday enjoying the last bit of time I’d have with Taylor before I returned home. I wanted to soak up all that I could in the amount of time I had left. And, too, I was conflicted about the line of work Taylor had elected to pursue. While I had a somewhat limited knowledge of what porn was about in terms of those who participated in it, I did realize that it often had far more negative consequences than some people realized. But I also knew that she was very smart and would not have gone into it without understanding what she was getting into. I left town with a whole new perspective than I’d had just one week earlier. Only time would tell if that was to be a positive or a negative.

1. This was mid-2001 [↩]
2. That’s a whole other story [↩]

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Tagged as: Alexa, anal sex, dildo, enema, porn, Taylor