Taking It To The Next Level...

When most people decide to become more serious and take their relationship to the next level, they usually talk about being exclusive and setting a bunch of rules for their new budding romance. (Gag me.)

My idea of taking things to the next level doesn’t exactly involve picking out china patterns. When I decide to get more serious with someone, I make him my “Number One.” In other words, his dick is getting the most action from my lady parts.
So Brian decided that he wanted to take our so-called relationship to the next level (not exactly a shocker).

Due to my line of work, I get tested monthly. I’m a disease freak, and I don’t exactly want crabs covering my beautiful pussy. In order to take things to the next step, I told Brian that he had to get tested and show me his results. It’s kind of like a foreigner trying to get citizenship in America – his dick had to get a green card in order to set up camp in my vadge. But I already know he’s not “the one” for my pussy but still want to see his results. I’m still testing out others. Hey, I’m a popular girl!


- Sienna Sinclaire® - The Single Girl®: Your Naughty Lifestyle Guide

The Anal Lover

You should know by now that I’m not like most girls. Many times women want to feel a special connection with a guy before she’ll allow him to enter her backdoor. She wants to have dated him for a while and have all those warm fuzzy feelings before she’ll open up her keister. My vagina’s not made of stone, but I don’t need those mushy feelings. If I’m in the mood for a good butt fuck, I don’t have to know the guy for very long before I’ll bend over. Sometimes I need to give my vagina a break for the night.

My third date with Seth was pretty standard. We started off our night with dinner before heading to a popular dance club. I drained several drinks to loosen me up (not that my vadge and I really needed it). Little did I know, my ass was about to experience a whole new anal world.

When we got back to my place, we almost immediately started bumping uglies. This was our second time having sex, since I didn’t give it up so quickly on our first date (Girl Scout Badge for me!). Usually if I like someone, I like to make him wait. If I fuck you on the first date, it’s not because I care about you. It’s because I’m horny and you’ve got the penis I need. I don’t actually care if you ever call me again.

Seth started off fucking me vaginally, but it wasn’t long before his one-eyed willie was trying for another entrance. My ass is no Virgin Mary; she has already taken in her fair share of huge cocks. Seth had a big dick, but it wasn’t as wide as some I’d taken up the tailpipe. I knew my ass could handle him.

His cocked slipped perfectly in between my tight cheeks. Anal always makes me come as fast as a thirteen-year-old boy. I quickly came all over his cock, and he followed soon after. God, it was amazing.

“Perfect,” I thought. “It was such a nice night out, and this was a great ass fuck! Now I’m ready for bed.”

After we both get cleaned up, I came back to the bed. His cock rose to greet me. I couldn’t believe he was already hard again. I would expect that from someone in his twenties, but Seth is in late thirties! It was a nice change of pace. Normally my dates’ penises can’t keep up with my horny beaver.

He was hard as a rock, so I decided to reward him for his sexual stamina. I began using another hole he hadn’t yet experienced. I worked his dick in my mouth, blowing him well. I knew there was no way I’d be able to finish him off, since he just came in my ass. But before I knew it he was coming again! Normally I don’t let guys finish in my mouth. Does anyone really like the taste of cum? It isn’t exactly the whip cream on top of a meat popsicle.

Seth, however, was in a league all his own. He had the best sperm I’ve ever tasted. It was clean, clear, and clump-free. I let him fill my mouth and swallowed it with ease.

After blowing him, I passed out. Surely, he was exhausted too. I wasn’t asleep more than twenty minutes before I felt him rubbing against my body, slowly trying to wake me up. This guy was like fucking a twenty-year-old boy. He gently caressed my skin until I started to stir. He immediately noticed that I was waking up so he began rubbing my breasts, letting me know he wanted sex again.

“Holy shit,” I thought. “What the hell is this guy on? Can’t he let me just sleep until the morning?” I am, after all, awesome at morning sex. I always have extreme lady wood.

Instead, I decided I was up for another round. I mean, how many times did I have the chance to fuck three times in the span of an hour and half? This time he went straight for my ass. Apparently his dick didn’t need a map or an invitation. It felt just as amazing as the first round. I started to believe his dick was made of gold.

When we both finished, I hoped it was for good or at least till the morning. I was going to get spoiled on all these orgasms in one night. Thankfully, his dick calmed down after round three. He had to get up early for work so there was no time for morning sex. My ass was happy to see him leave; I needed to recoup before my buns met his powerful bratwurst again.


- Sienna Sinclaire® - The Single Girl®: Your Naughty Lifestyle Guide

Mr. Personality

My vagina is like a metal detector. Instead of finding loose change, it’s constantly turning up annoying habits of all the ball-sacs trolls I date. Sometimes they’re hard to find, like the penis of my first sex partner, but most of the time my dates’ irritating habits are staring me right in the face (like the cock of every guy who begs me to blow him).

While I appreciate the effort, if a man has the personality of a brick wall… I’d rather you just shut up and nut up. Otherwise, I’ve got a dildo back home that can get the job done. Unfortunately, those with the worst qualities almost always think they’re God’s gift to vaginas.

I met this guy out at a bar one night. He seemed harmless on the outside, definitely fuckable but nothing my lady parts and I couldn’t resist. But the second I discovered my date was on a first name basis with our bartender and everyone else at the bar that immediately threw up a red flag for me. Don’t get me wrong, it’s not like I hate friendly people I just don’t like overly friendly ones. I could barely remember his first name and I didn’t care about learning his last name. The more he talked, however, the more I realized I needed an alcohol-IV pumping in my arm, before I could handle this guy and all his charisma.

It’s a mistake to think that charmers can easily sway my vagina and me. Sure, I may laugh at your retarded jokes. I’ll smile and nod when you pretend like you’re the greatest thing since a six-inch vibrator. That’s only because I want to fuck you. You’re not actually funny. I just want to get in your pants and introduce you to my meat cleaver. One-eyed willies have a much better shot to impress me than the giant hole in a guy’s face that he can’t ever seem to fuckin’ close.

The date proceeded to get more annoying with Mr. Personality when he started using my name in almost every sentence.

“Sienna, what do you do today?”

“How’s your drink, Sienna?”

“Don’t you love this bar, Sienna?”

Listen, I’m not about to blow you because you remembered my name. I can barely remember yours, Einstein. My hair may be blonde, but I know my own goddamn name. You’re not earning yourself any points by reminding me that you know who I am. The only time I want to hear you say my name is in the bedroom. (Cause let’s face it, you totally will.)

For some reason (I blame my vagina) because I let him take me out to West Hollywood a few days later. Every pore on this guy’s body was dripping with charm. He seriously needed to put a cork in it.

When we got to the restaurant, the hostess greeted us. My date smiled and told her the name of our reservation. By this point, I wasn’t really paying attention to their conversation. I knew I was going to have to listen to him for the rest of the night, might as well enjoy the few seconds of reprieve.

All of a sudden, I heard something that didn’t sound quite right. My date and the hostess laughed. She looked super uncomfortable. I thought maybe I had heard wrong. After all, I wasn’t really paying attention maybe I had missed something. Good lord, I hope I missed something. Surely he can’t be that lame…

“What did you just say?” I asked.

“I told her my name for the reservation, but then I said how funny would that be if I said we were here for a spa appointment?” he said, cackling like he had just come up with the best joke ever.

What the fuck? I thought. Here I thought I had missed something, but I hadn’t. That was his joke and he was serious as birth control.

I flashed him by famous “are you fucking kidding me” look. I didn’t laugh or smile. I just turned the poor hostess and said, “Didn’t there use to be a nightclub next door? What happened to it?”

I changed the subject as quickly as I could, but I couldn’t avoid the damage his lame-ass personality had already caused. How embarrassing! For the rest of the night he tried to entertain me with his wise cracks, but I wasn’t amused. I wanted to skip to the part of the night that was actually pleasurable, getting fucked by his huge cock.

After that date, I only invited him over to my house to bang. Cut the small talk. I had to get him to close one hole, so he could open another.


- Sienna Sinclaire® - The Single Girl®: Your Naughty Lifestyle Guide

The Singer

One night my girlfriend and I decided to treat ourselves to a night out on the town. We hired a personal chauffeur and booked dinner at the Chateau Marmont with bottle service at Voyeur. We were all set to pick up my latest condom flavor of the month, Matt, who dressed and sang just like Frank Sinatra but looked much hotter. Before we picked him up, I felt a strong obligation to forewarn my driver and my friend about him. His vocal chords (like his dick) had a mind of their own, and I needed to tell them that my date would more than likely be bursting into song at some point in the night. He’s an amazing singer, don’t get me wrong, but there’s a time and a place for singing and that’s the stage. I don’t care if you’re a professional singer. I’m a “professional” too but you don’t see me taking my clothes off whenever I go out (that part doesn’t come till later).

We picked the guys up and headed to dinner. Two milliseconds later, Matt broke into song. Singing is one of the most annoying things you can possibly do (when not on stage) – especially when you’re in a car with little space because your voice projects louder. My ears were literally bleeding.

My friend nudged me, as soon as he started singing, trying not to burst out laughing. My driver kept staring at me in the rear-view mirror and I know he was dying to make a smart-ass comment. I did everything I could to keep it together so as not to start laughing. You could cut the awkwardness with a tampon. I mean, who the hell did this guy think he was? It was almost as if Matt expected my vagina to instantly go weak in the clitoris by his voice. Up to that point, I had definitely been turned on by him singing on stage but not in the car.

Finally, his ballad ended and we made it to the restaurant. I silently prayed that he wouldn’t break out into song again while at the Chateau Marmont. After an uncomfortable dinner of trying to keep him talking instead of singing we got back in the car and head to the nightclub. The club didn’t open until eleven, which meant we were gonna have to do some serious drinking in order to get buzzed before last call at two.

We got to the club a little bit before eleven, so my driver suggested driving around the block to kill a few minutes. Matt, of course, had other ideas.

“Why don’t I sing a song?” he offered, as though we were all dying to hear him sing for the millionth time. Before I could intervene he broke out into another song, and we all sat there awkwardly. I stared at the floor, cursing my vadge for being so attracted to this douche bag. I wanted to chop his balls off and stuff them in his mouth. How could he not see that we were obviously NOT interested in listening to him? I thought.

“Encore!” my driver said in his British accent after Matt finished. (There’s a gay joke in that last sentence somewhere.) His voice was obviously dripping with sarcasm.

Before Matt could open his mouth and blurt out another song, I immediately leapt over the armrest. “Let’s turn on the radio!” I yelled, reaching for the dial. The only thing I wanted Matt to open up was my vagina, and I wasn’t even sure about that anymore.

Pretty soon, we got into the club. I half expected Matt to harmonize with the DJ’s music. Last call couldn’t come soon enough.


- Sienna Sinclaire® - The Single Girl®: Your Naughty Lifestyle Guide