Period Sex.

It's been a while since I've been with anyone who wanted to have sex while I was on the rag. Roseboy is more than willing, and that's fun.

Now, I know I have mentioned The Keeper before, but not gone into much detail. A detailed post about it is to follow, I promise, but a quick note about it is this: with the Keeper, you can receive oral sex on your period. Yup. Believe it. The Keeper contains your menstrual fluid safe and sound in a rubber/silicone cup that suctions around your cervix, high up in your vagina. What's especially great about it is that it leaves the walls of your vagina clean, and unlike tampons, doesn't absorb your normal vaginal fluids along with the menstrual ones. Therefore, with the Keeper in, you can still get wet when you're aroused, and those fluids stay separate from your period blood. When your partner licks you- all they taste is your sex juices.

So yeah. Anyways, even though I could have pushed for oral, I decided I'd ease him into the period stuff, and took out my Keeper so we could have regular sex. (You can't have intercourse with it in.) We layed down towels, and then I got an idea.

Since we weren't going to have oral, why not get things nice and lubed up? I broke out some Pjur Eros, a really nice silicone lube, and my Black Dragon latex gloves. Now, I know some of you might not get the point of gloves, but hopefully this post will illuminate that for you. And Black Dragons make the latex glove things super sexy, since they are perfectly fitted, textured, and jet black - made specifically for sex. If you can't see the sex appeal with gloves, just think of that scene in Fight Club where Brad is fucking Helena Bonham Carter wearing nothing but big, yellow dishwashing gloves. Mmm.

Anyway, the glove thing led to some unexpected but incredibly exciting activity. We started out with a lubed genital massage, but since our hands were protected from anything potentially "icky" they started to wander to new and previously undiscovered territory.

We had briefly discussed the anus before, and I expressed some curiosity. He seemed to have no inhibitions about it as he felt around and began to probe me. I followed suit on him. This was exciting, and very new for me.

I had read some books about anal play, but never tried it. The books gave me the impression that anal play was a lot more complicated than it proved to be. I thought I would have to be relaxed to the point of pudding in order to allow a finger in, and that it would take some serious concentration to get to that point. Not so, my friends. With a little Eros, I was enjoying all the benefits of being finger fucked in the ass in no time! He told me later he was only getting up to his second knuckle, but it certainly felt like a deep penetration. Because I was at a bad angle, I didn't get too deep into him, maybe just my fingertip, but I was also afraid to hurt him.

And then he fucked me. He fucked me with his dick thrusting in and out of my vag, and his finger thrusting in and out of my ass. My finger was in his ass as he fucked me. Double penetration was something wonderful I never expected. "I can feel my finger with my dick!" He exclaimed.

I don't know what it is, but I love the idea of being penetrated so completely- every hole, so much so that no matter where I move, I can't escape. This is partly why I love being eaten out and finger fucked at the same time- and why it makes me come every single time. No matter where I wriggle, I can't break free from the sensations forced upon me at every spot at once. Obviously my next step needs to be getting eaten out with a side of SHOCKER.

Anywhoo, it was amazing sex. And, as always, he collapsed his sweaty head on my chest and let me hold him. And all we had to do was rip the gloves off, and we were clean and cuddle ready. We still had silicone lube all over us though, which doesn't reabsorb into your body, so I pulled him into my shower.

I sometimes think back to around February of this year, when I was dating Mr. Abstinent Conservative, and wonder how the hell I managed.

Hey hormones! You suck!

Things continue to be on the up-and-up with Roseboy. The other night we had one of those amazing nights where we talked about our feelings, and got to admit how much we like each other.

Most of our statements were prefaced by the phrases: "I don't want you to think I'm a freak, but..." or "I'm probably going to scare you away, but..." It's funny to think that nowadays it makes you a freak to admit you would like a serious relationship, or it could scare someone away that you actually really like them. In the end, he said, jokingly, "Would you wanna be my few-week girlfriend?" I said, "Yeah. I wanna be your girlfriend."

So... I guess here are the stats as they now stand.

V, age 21 years.

• 2 serious boyfriends to date, 1 semi-serious, and 1 current something
  
• Lost virginity to one of them at age 19
  
• Had sex with 8 people in 2 years (Started this blog at 4 people)
  
• 5 out of 8 were one night stands, 1 out of 8 was an ongoing hookup, 2 involved feelings
• Have been involved in some way with: white Protestant guys, Irish Catholic guy, Italian guy, black guy, Moroccan guys, Spanish guys, Chinese guy, Jewish guy. (I enjoy collecting ethnicities.)
• Haven't felt this way about a person since: High School (I think...)

I guess when I get into a new relationship, I like to take stock of my history and, well, my dating "status" if you will.

Last night Roseboy and I went on our first real date. We got dinner together at a really neat place (he wanted to pay but I wouldn't let him) and then went to see a total guy-flick chock full of guns and explosions and punching (I let him pay.)

After the movie, he turns and says, "Wow. I really got lucky." I guess not so many girls like bad-ass shoot-em-up movies... but I do. I also like to have sex all the time, to give head, to play DDR naked... just about the only thing that keeps me from being the best girlfriend of all time is that I'm not a sports fan. But neither is he, so it works out.

After the movie, we went back to his place. We both had to get up early, so we budgeted about an hour for a fuck-fest and then I was gonna go home. But neither of those things happened quite right. For some incredible reason.. I wasn't in the mood. And no matter how determined I was to get something done, I just wasn't. And he could tell. And it was embarrassing.

He said all the right things, like "I don't expect anything," and "it's really okay, I like cuddling." But I hate it all the same. I wanted to fuck his brains out- not get all emotional and vulnerable in his arms. I wasn't ready to show him that much crazy just yet. But at the same time, all I wanted in the entire world was for him to hold me and brush back my hair and tell me everything was going to be okay......... when everything WAS ok!

There was absolutely NO REASON to feel that way- the night had been great, and my life is generally pretty flippin' awesome! Yet... I was sad, scared, and vulnerable. I HATE not being in control of my own emotions. It took me between 2 and 3 hours to leave. We did have sex though... really slow, regular, "tender" sex.

I checked the calendar this morning. My period should arrive today or tomorrow.

Fucker.

Sitting on Faces

Just yesterday, I was reading My Favourite Life's post about sixty-nining, and although it had been on my mind for a while, it cemented for me that the 69 would be Rose Boy and my next adventure.

Last night we spent some time hanging out in town, back at that spot of our magical night, and said sweet things to each other, which led to kissing, when led to me needing him in my bed that instant. (I would have come close to fucking him out in public if it weren't for the chill and the wet grass.)

I went to pee and when I came back to my room, he was laying on his back, horizontally across my bed. His head was hanging off the edge of the bed. I stood by his head, leaned down, and kissed him. When I stood up, he stretched out his head and lucky for us, his head pressed perfectly between my thighs. He bit the crotch of my jeans.

"Watch this" I said. My jeans were stretchy and a little too big, and I slipped them down over my hips. His greedy hands reached back and pulled down my underwear, and he shoved his face in there, his mouth taking in my lips from top to bottom. The sudden sensation of it lurched me forward, and I bent at the hips, my top half falling on top of him, where I ripped off his belt and started on his button fly (goddamn button flies!)

Pretty soon we were sucking each other in unison, with me standing on the floor bent at a 90 degree angle, him with just his head off the edge of the bed. Amazing.

Unfortunately, my legs started to hurt. I didn't realize it but I had been standing on my tip toes for a while. A few extra inches of height would have helped, so we stopped and I climbed into bed with him and started rubbing him. I looked back at him, and he said, "You're so sweet."

"Do sweet girls do this?" I asked, and threw my leg over his head, and lowered myself down onto his face.

It was good, and after a relatively short time, he warned me that he had to stop himself from coming. As it turned out, I was on the verge myself. "You don't have to hold back for long," I told him.

In less than a minute, I was coming. And as I hit climax, I tasted him release in my mouth. Perfect synchronization.

This whole experience was especially cool for me because this is only the second time I've ever sat on someone's face. The first time was with Jockjerk, and I was too uncomfortable to enjoy it. I feel like the idea of sitting on a face is an especially terrifying one for girls who don't consider themselves lightweight. And this was the first time I had ever done it in the 69 position, aka, facing the opposite direction.

This had always really made me nervous because I truly hated the idea of having my guy's eyeballs that close to my asshole. Especially in a close-up, spread-cheek, straddling situation. But Roseboy actually made me feel comfortable. It might have been the tiny stroke he gave my asshole at one point, or that he told me how hot the whole experience was for him afterwards.

But this time, as comfortable as I was, I am still not 100% confident about my anus. It has hair, and unlike other parts that are easily shaveable, waxable, or even trimmable... my arsehole is not. And I feel like that is a place a girl is not supposed to have hair. I guess the porn star standard still feels more right to me than reality in this case. Not proud of it, but it's the truth.

Not to kill the mood of the mood of course. It was amazing, and I will definitely be doing it again. And afterwards he ate me again, this time for a very long time, and my second orgasm lasted for close to a minute. I could really get used to this.

And still later yet, we fucked. By the time he came, he had worked up quite a sweat. We were both soaked in it. And he was so exaughsted he collapsed on me, his head on my breast. That is one of my favorite things in the world, there's something so maternal about it. But not in a creepy way... in a tender way. I held him to me as long as he could stand to be wearing a cum-filled condom.

And a little drama for good measure.

So this past weekend, after Rose boy and I had sex for the first time, I went on an all-out CRAZYFEST that could probably have won me a spot in One Flew Over the Cuckoo's Nest.

The next morning I emailed Rose boy to tell him what a good time I had. He didn't write back. So I started wondering if something was off, and yes, now that I thought about it, something had seemed off that night, and hmm... perhaps he was upset about having sex... did I say anything? Oh fuck...

He asked me if I thought sex would change things between us and I said no. Then during the aftersex cuddling, he asked me if I felt any change, and I said no.

So then the obsession started. Was that the wrong answer? Was he hoping I would say I felt differently? Does he wish we were more committed? Does he realize how much I actually like him? Does he think I'm using him? For sex? And so on...

The next night and I got drunk and texted him a little hello. And even though I did it after midnight... I was super paranoid at that point, and got even more upset because he didn't text back.

By the next day (2 days after sex) I was flipping out. I couldn't stop thinking about what I must have done wrong. I was basically prepping myself for this whole thing to be over... I was honestly trying to prepare myself for what seemed inevitable at the time: that he was never going to call or contact me again.

And then, midday, he texted me a friendly message. And I texted back. And he texted back. And it all seemed normal. And I felt incredibly relieved, but still a little suspicious.

The next day I got home, and resisted the urge to call him. Later we talked online. Friendly, normal. We made plans to hang out that night (last night). And it was lovely. The perfect night actually. Watched a movie, cuddled the whole time, and then hooked up in my parents' basement. And the sex was even better. And I was so glad that he never witnessed my "crazy bitch" syndrome.

Then this morning, he sent me a reply to my original email. The one that started this whole thing. "How strange," it said. "You sent me this email on the 13th but I didn't get it until today."

Little Miss Goldicocks

The other night Rose Boy and I had sex for the first time.

But before we even get there... oh man... my vag is shuddering just thinking about it. He ate me out. And boy howdy was is good! This kid knows what he's doing, even though he doesn't claim to. He teased me for quite a while, licking, biting, sucking on my thighs, stomach, and occasionally grazing my lips with his tongue. I was grabbing the sheets even before he plunged in. And when he did... ah, amazing. He used his hands, alternating and hitting my g-spot effortlessly. And then after an appropriate length buildup, he started giving firm, long strokes up to my clit with his tongue, while he pumped his finger against my g-spot... and I'm pretty sure his roommate heard me come.

Later I gave him a bj for his efforts, being sure to give plenty of attention to his nipples. We got to the point of no return when he said, "You're gonna make me cum! Do you want me to come?" And I looked up at him, still licking and kissing his cock, and said, "Well that depends, do you want to fuck me?" He said he did, and since it would be our first time, I asked if he was sure. He said he was. I decided to suck him just a little more, then changed my mind, and kept going, harder and deeper. He came hard. "I changed my mind," I said. "I noticed," he said.

Later on, it was getting late, but we had gotten ourselves all riled up again. He asked me what I wanted him to do. I brought up fucking again. "Are you really sure?" I asked. "You seemed to want to wait." "No, I'm sure."

And it was awesome. We put on the condom together. And it hurt for about three seconds when he first entered me (it's been a while). But then, oh baby.

I know a lot of women like big dicks. I am not one of those women. Sure, they're aesthetically pleasing and when you get one in bed there's definitely a "wow" factor invovled... but in my experience, they just plain hurt. I guess I have a sensitive cervix and with a big guy, missionary is just about the only position that isn't horrendously painful, and sometimes even that is a bit much. Usually with a big guy, I can't come because they hit my cervix, not my g-spot, and I usually get too sore to go for more than a few minutes. Usually, I'm just lying there, doing my best to act as hot as possible to get them off quickly so they'll get off me quickly.

Now, a medium sized dick? That's where I'm at. It fills me up just fine without hurting. On every grind, my g-spot is pleasured. I can put my legs over his shoulders or do rear entry and all kinds of other things when I'm not in pain. Truly, I prefer it. Rose boy's dick was just about the perfect size. Not at all small, but not gargantuan either. My notorious vag salivates in anticipation of a dick like that, instead of clenching shut with a "You best be kidding."

So, I guess what I'm trying to say is that the sex was good. And that's even more impressive when you realize the fact that most of the time it takes people a few tries to really get their groove on together. But we grooved.

I'm not the kindof girl to get all sentimental and emotionally attached over the act of intercourse... but I do occassionally get caught up in the ideas of "fate" and "destiny" and can't help but wonder if it means something for Rose boy and I to be so sexually compatible...

What's on the Menu

Since I met Rose boy, I've been living off of these things:
-Breakfast.
-Lunch.
-Sweat.
-Ear nibbles.
-Nipple sucking.
-Skin biting.
-Saliva.
-Cum.

Things I haven't been eating:
-Dinner.
-Snacks.

Since we got together (albeit it's only been four days) I have had very little time to eat, passing up dinner and afternoon snacking to consume him each night. Even tonight, the first night I haven't seen him, I skipped dinner out of habit. I'm a bit hungry now at midnight, but in about 3 seconds sleep will overrule food.

This could prove to be a very simple and effective diet plan: Substitute Sex for Dinner. Oh, and add some Naked DDR in the afternoons, and you're set.

If it works, I'll publish a book and distribute the profits among fat-camps across the country to fund hookers for the chubby kids.

Perfect Guys and Not So Perfect Timing

Sorry I wasn't able to update for a couple days... I was too busy making out with a GORGEOUS boy.

Yes, my date with Rose Boy went really well. We walked around town a bit, and then decided to go watch a movie back at his apartment. And it was a good time. And then we made out for around four hours.

Here is what first tipped me off about the amazing Mr. Rose Boy:

He has this book, my Bible.

Yes, he wants to be a sex therapist. Yes he knows of feminist empowerment sex shops in the area. Yes, he is open about sex. Yes, he is experimental. Yes, he is not afraid to ask for what he wants. Yes he wants to use toys on me.

How did such a perfect guy fall into my lap? *Thank you Craigslist!*

And did I mention how cute he is? Oh man. He's a little guy- barely a centimeter taller than me, and I'm 5'3". Still, he is so attractive. He wears these awesome jeans that make his butt and package look so cute. And t-shirts. God I love a guy in a t-shirt and jeans. He's kinda punk-y and has tattoos!

This is my first tattooed man, and I really like it. He has a word that I wont disclose for privacy's sake above his right nipple (your left.) Oh, and his nipples.... this kid goes absolutely insane when you get near his nipples. Absolutely i.n.s.a.n.e. I like it. I love being able to drive him crazy. And I did.

I saw him again last night (two in a row! whoo!) and it was even better. This time we cuddled and made out in the nude. He makes me feel pretty comfortable with my body because he isn't afraid to throw out a few "you're so hot"s or "you're so pretty"s. And he grabs me and slaps me and runs his hands all over me....

He's artsy, alternative, hot, Jewish, and the potential for something real is, well, it's real.

He turned to me and said, "This is an odd hookup." Why? "Well, we kiss a lot and look into each others eyes, and play with each other's hands..." Yeah. It seems to be a little more than just a hookup.

He said he will just have to keep reminding himself that it is a hookup. I said... "well, maybe we could think of it a short relationship." He said, "An open relationship. That's what you would want, right?" I thought that was cute. I guess I do give off a bit of a non-monogamous vibe. But I said, "No. When I like a person, I'm not interested in anyone else." He seemed surprised, but pleased. "You're a faithful girlfriend?" he asked playfully while he snuggled into my neck. "Yes."

Like I said, potential.

And I leave the country in less than two months.

Is it worth it? Should I set myself up for heartbreak? Is it fair to set him up for heartbreak?

Rather than think about it, I sucked on his nipple and pressed on his taint, rubbed his balls and cock, and then gave him a spectacular blow job. When he came he screamed in a way I've never heard any guy scream before. Wow. Awesome.