You Might Be Hot, But I Liked the Dogs More

After an already pretty productive week (I had already seen West Point, Fickle Daddy, and Mr Fantastic this week), I was still sexually wanting. My insatiable sex drive needed more of something; more variety, more penis, or more orgasms–just more. This is where House Sitter comes in.

I matched with House Sitter on Tinder and for over a week he would ask me to meet up or come over to the house he was at. These requests would be during the day, right after work, or my favorite time–2am. I am obviously not a huge fan of booty calls, mostly because I am passed out by then and that bed is real comfortable after 10:30 at night. But I digress…When I matched with House Sitter (HS), his pictures made him look about a hard 8, and with his age of 22 I was hesitant if this was going to be a good choice or if I was going to get a “show me ur tits” within 3 messages. What can I say, past experiences can leave a girl leery. HS was very upfront about wanting to meet for what one could only hope and pray was not disappointing sex. Within just a few messages, House Sitter asked for my number so he could share pictures of himself, and that’s when I became the receiver of a beautiful dick pic. When I say beautiful, I mean it looked like it would make Catherine happier than a fat kid on dessert day. With his first invite, House Sitter enticed me with promises of massages. This was incredibly enticing, especially when I know I have the worst back ever. However, life and sleep got in the way.

Meeting up with HS was easier sad than done; I matched with him the Monday and he got straight to the point. I saw Fickle Daddy and Mr Fantastic that following Tuesday and didn’t really need to see three guys in one day, especially since I already had an orgasm with Mr Fantastic. I drug my feet on seeing him in person; this tends to happen when you’re busy with life and already have someone to help with most of your sexual needs. I eventually had free time to see House Sitter on Wednesday afternoon. Before getting ready to head over, I asked him if he had condoms; he did not have any, so I instructed him to go get some (I’m not a condom delivery service.)

He lived about 20-25 minutes from me, so I figured that plus my lazy way of getting everything together before leaving would be enough time for him to literally drive across the street to get a box of condoms. Boy, was I wrong. When I arrived at this fancy house on a golf course, I was greeted by a shiny and new sports car in the driveway (possibly his since there were clothes in the car and looked like a 2nd year senior’s car), House Sitter, and a great dane sized dog at the door. I was in love–that dog was the sweetest and gave the best big dog kisses ever! There was even a second big dog with which to give my all my love to.  Yet, all I could focus on were the two dogs in the room, not the pretty damn hot younger gentleman that opened the door for me with a toothbrush in his mouth.


Just House Sitter and his dog

House Sitter was around my height (5’9), dirty blonde hair, blue eyes, and a fit frame. To say he looked like the well tipped bartender of a college town is an understatement. He quickly informed me that he had not gone to buy condoms. I think my expression went from, I LOVE DOGS, to, the fuck is wrong with you, bitch?, real quick. We don’t do sans condoms with a guy that looks like that, ever. That is chlamydia real quick, and I’ve had that enough in my life. I responded to his failure by saying “Well we should go buy those before we start taking any clothes off.” He offered to drive to the store, and I was ready to go. That shiny sports car was made for tiny people with tiny legs. I am tall with big thighs–I did not enjoy the clown car ride to the local pharmacy store to get condoms. Once there, he left me in his car to go procure anti-STD protection. I then texted my safe buddy to let them know where I was and that I could over power HS if needed. When HS returned to the car, he decided to not only flash me the condoms he bought, but also that they had this “fancy” sex oil. He bought the Trojan massage oil; I don’t know how that’s fancy, but it was to him.

Once back to the house, he directed me to the side bedroom he was staying in, away from the adorable dogs sadly. He turned on a side table lamp while I noticed he had thrown a sheet on top of the bed, which he said was because of the dog hair. Immediately House Sitter started to get undressed and asked if I wanted that massage. I quickly responded and said yes and asked how far I had to be undressed for this as he stood in front of me in his boxer briefs. He didn’t respond, so I just stripped down to the panties I had on and laid face down on the bed. HS walked over to where I was on the bed and straddled me with no warning as he poured what felt like half the bottle of oil on my back.

Cold. The oil was so cold and it hit my only ticklish spot–my spine. I flinched and bucked up into him something fierce. He told me to calm down. Don’t tell a woman to calm down when you have her basically pinned down in a strange house with cold liquid running down her back. I assumed the dogs may have saved me in the end, they knew I was their kind. After massaging my back he pulled my panties off not with his hands, not with his feet, no HS went all porn style by removing them with his teeth. How could I tell? He would move them down, kiss me, remove from another side, kiss, and repeat until they were at my knees. While this sounds like it’s leading up to some slippery sex, it led to a lot of massaging of my ass.

Pushing my cheeks together, spreading them, pushing up, pushing down–it was a nice muscle massage if I needed that.

House Sitter was so quick to put on the condom that if I hadn’t seen it afterwards I would have thought he didn’t use one. He wasn’t into kissing and didn’t want me on my knees for doggy, just laying on the bed so he could fuck me that way. Why didn’t he want me in a better position? Probably so he could fuck me between my actual ass cheeks. I didn’t know if I should tell him that that’s not how sex works, but I just laid there. Eventually he entered inside me; his cock was decent sized, but I couldn’t feel it that well from the angle he used to fuck me. I tried to push my ass up into him as much as possible, but it just wasn’t as exciting as I wished. It didn’t take him that long to change positions; he had me roll over onto my back so he could play with my boobs while on top. Not too long after, he came, rolling off of me and getting up to get a towel for me. I asked if we could cuddle, to which he shrugged it as a yes.

House Sitter was not a fabulous cuddle companion, but at least I got some cuddles before trying to turn him on again. Because I didn’t give him head before the first time, I didn’t notice that he literally dunked his crotch in cologne. The smell of men, in forests, and their big beards was really strong on his trimmed pubes. His cock didn’t make me gag, but the smell did. Unlike other men, I wasn’t down there as long as I would have normally been. The second time was not as long as the first round, but at least I got to feel all of his cock this time around.

Once done, he said he was going to take a shower and I said I would clean up and put clothes on. When he came out of the shower (which was a drug out shower, honestly), he was overly surprised to see me still slowly getting ready. My bad, I had to check my phone and respond to work e-mails. I apologized and said I would be leaving shortly. I grabbed my things, kissed all over the dogs, and went on my merry way.

House Sitter reached out to me a few more times before he went back to school/work/wherever he came from. While I enjoyed it enough, he wasn’t really something more than a one night to me. I was also in Houston pretending to enjoy the company of someone with a tiny penis and a horrible alpha male personality.

Lesson Learned: If your gut ever feels weird, it’s probably going to be weird. Also, dogs make or break things, and if he was staying around and they were his, I would have been around 24/7.


The Daring Vagina

Sin City Part 1: The Return to Familiarity, or How I Earned My Way to the Airport


Oh hell yes, monster wang!

As mentioned before, I had masterminded an AMAZING craigslist ad but awkward experience that made me feel like I was back in the swing of things. Well, back to familiarity at least. With any posting on craigslist, you receive some losers, some “meh” responses (“R u real?”), winners (able to string thoughts together and responded with what I wanted), and my favorite–the repeat replying men. Sometimes, they’re losers, but sometimes they happen to be people I’ve slept with (I have to admit, it’s happened a few times.) For those that have followed my blog since the beginning, you might remember The Joker. How did he wind up in my bed?…again? He replied to my ad with his picture and a short description (just like the first time) that really is eye catching. I was in a, don’t fuck with me since I’m basically the greatest thing to happen to you in the bedroom, type of mood and responded to his email with:

We’ve fucked before. You stopped texting me. I think I’m good.

He instantly replied to my email and asked if I was me (by name I might add), and I was standoff Daring Vagina for multiple responses, until I remembered that he had amazing stamina, and his cock was pretty fucking phenomenal to boot. Reason or sexual appetite? What is a girl to do? Get back on that cock, obviously. We texted (I still had and also still have his number), and he even mentioned he remembered where I lived–no address needed. I only felt slightly concerned over that fact, but he did come over a few times before, and even I remember how to get to places I’ve been to.

We played tag team on getting together; we had opposite open schedules for the most part (or I would have slept with him and called it a day.) I had taken off early from work for my Vegas trip and told him I had a window to meet up if he was available. The Joker jumped on it; he literally was so excited about it that he beat me to my place. I saw him him in his truck (he owns his own construction company and he’s built like a construction worker) and when I got out of my car I just gave him a look. The look of, are you that impatient and ready to fuck me? He got out of his truck and was all smiles with his amazing green eyes and his, what did I do?, facial expression. I just shook my head and told him my time frame for our rendezvous. He followed me up the stairs and replied with, you better be ready to start the minute the door closes. I stopped, turned to look at him with another look, and he responded by smacking my ass. Yes, I was completely ready to fuck him again.

After closing the door and locking it, The Joker immediately pinned me against the door, creating the feeling of a lust filled moment from a movie. He immediately started to undress me from my work clothes (I’m 95% sure it was slacks and a nice top with a cardigan with nothing remotely sexy underneath) and led me to the bedroom, leaving discarded clothes in our way. Once I was in just a bra and panties, he slowed down, leaving a trail of kisses down the side of my neck, biting at my clavical before picking me up (as well as he could, which was probably the greatest testament to me that I had lost weight) and tossing me on the bed. The Joker continued kissing down my stomach and once he was at the top of my panties, he pulled them off with his teeth. Once they were on the ground, the slow and tenderness of his touch had left, and the eagerness that I always associated with The Joker returned. He pulled me at my hips until I was on the edge of the bed, knealed down and then spread my legs apart as he furiously licked from my clit to my ass. It didn’t take long before I told him I needed to suck his cock; he stood up as I slid off the bed and onto the floor. It was like fitting your feet into your favorite brand of shoes; the taste, texture and feel of his cock in my mouth and in my hands was refreshing and perhaps a perfect fit. He moaned out my name each time I did my best to take his cock down my throat–it was the best type of praise. It didn’t take long before he told me to lay on the bed.

He slowly pushed his whole 8+ cock into me as he nibbled on my ear. I was in ecstasy; he obviously remembered my weaknesses and my wants while under him. The Joker slowly got rougher with his thrusts, pushing my legs farther back. I had no idea I was so flexible until my legs were so far stretched that I had my knees by my ears. It didn’t take long before he came the first time. The Joker always came hard and loud; he grunted as he slammed into me. He slowed down a bit to regain his hard on and asked how I wanted to be fucked. He hadn’t fucked me since I knew my combo to orgasm success. I told him I wanted to be fucked doggy, vibrator on my clit and his thumb in my ass. Grinning from ear to ear, he kissed me like a dying man as he pulled out of me. He easily helped me flip onto all fours (by physically flipping my hips and moving me into the position) while I looked for my vibrator next to my bed. Once found, I placed it between my legs and smiled into the pillow my face was smashed into. After a few good thrusts, he pulled on my hair to lift my face out of the pillow with one hand and his other hand cupped my face, his thumb at my lips. He didn’t have to ask, I instinctively put his thumb in my mouth happily. The Joker took his thumb back, calling me a good girl in the process. Once his thumb started its assault on my eager asshole, my vibrator went to work and it took little to nothing before I came on his cock. At least I have that down. He let out the most masculine grunt as he rammed his cock into me, cumming a second time.

Trying to catch my breath and not look as flushed as I was, I told him I needed a minute. He happily laid down next to me, grinning his adorable smile at me. I smiled back, my hair a complete mess around my face. “Hi,” was all he said, causing me to erupt in laughter. I replied with, Really? Hi? That’s all I get?, which caused him to also laugh. I finally regained movement in my legs, cuddling up to him.

The Joker stroked my body all over, creating goosebumps everywhere that could possibly have one.

I noticed his watch and asked the time. When he told me, I groaned. He gave me a puzzled look, so I told him I needed to call a cab since no one could take me to the airport. Without missing a beat, he replied that he would take me. I quizzically asked if he was sure, to which he replied that if it meant a third time he was very sure.

One more round later and we took a quick shower together; quick wash but no hair. Taking that sex hair on the road! Well, on the air. Once we were both dressed and ready, he carried my suitcase to his truck, opened my door and happily helped me into the truck. We conversed in small talk the whole way there, while he instinctively held my hand when I placed it down. I thanked him again for taking me; he said he was happy to take me. Once we were at the airport he realized he left his sunglasses at my place. Knowing my situation, he asked if it was ok. I shrugged and said I would figure a great excuse if needed. After helping me with my suitcase, he kissed me, and told me to get into trouble and let him know if I had the best sex ever while there.

Lesson learned: sex always gets better with practice.

If only I knew how much amazing sex I’d be having after him…until the next entry…

The Daring Vagina

Side note:
After my trip, I saw him two more times. He literally outlasted me and I had to tell him I couldn’t go anymore. That had never happened before to me. I pride myself on my stamina and he is way more insatiable than me by a long shot. Sadly, like before he vanished without warning. Amazing sex at least. It’s not everyday I find someone that loves to fuck me and has loads more experience than me, and not just in numbers.

Trainspotting Brings Out the Best in Me

Now that I have officially zipped the Perfect Baggage suitcase closed (pun intended), I can focus on what penis (and attached man) has made me the happiest: Tony Stark. As mentioned before, Tony Stark and I were friends; we were not booty calls, we hung out. Sometimes, we hung out and also had sexual relations. Below is one of the interesting and special sexcapades.

During one of our cuddling times post sex, we were talking about movies and the topic of favorite 90s films came up. Well, I have a list of some out there films that he had never even heard of, and then some he had never seen nor heard of. The one that made me playfully tell him I couldn’t have anything to do with his penis again was Trainspotting.


He had never seen what I consider to be the best drug movie ever. I told him, lucky for you, I not only owned it, but the movie theater we both enjoy was going to be playing it one night. He agreed to come with me if I wore a skirt. I topped that and wore a super fancy and cute pink dress that showed off my boobs. Yay boobs? Yes. Lots of yay.

Because I had been working long and dumb hours, I wore my dress to work. I was nervously asked by multiple coworkers and my chain of command if I had a job interview somewhere else. I guess I did look pretty when I wore make up and a fancy dress. Future interview outfit acquired! Well, I was able to leave work fairly on time, so I went home. I sat around, literally twiddling my thumbs until I could leave. I texted Tony Stark a bit and told him I was about to leave. He told me to leave the panties at home. Joke was on him because I never wear panties with skirts; I ran around so much at work that I wore bike shorts under my dresses so I didn’t rub my thighs raw. It wasn’t like I was lying when I said, you got it 😉, I just had something not pantie related on. Besides, I would totally take them off when I got there….

I got to the theater and easily found him; he’s a giant in a city of short people. He hugged me and then kissed my forehead tenderly. I told him that he would really enjoy naked Ewan McGregor in the movie, and he’d become a drug expert, since it’s so needed in his profession. He told me to stop being a dork and pick seats away from people. I happily obliged him. This theater wasn’t just a normal theater; it was the greatest theater ever, the Alamo Drafthouse! They served yummy food, amazing milkshakes, and so many types of beer…it was ridiculous. Why does this matter? You’ll see, or read.

We ordered food and beer while chatting before the movie started. As I figured, there were lots of empty seats not only near us but in general. People don’t appreciate the awesomeness that is Trainspotting. Once the movie started, Tony Stark took no time in putting his hand up my leg. What did he find? The bike shorts I didn’t take off. He shot me the look. I grimaced, looked to make sure no one was coming near us, or serving food, and quickly and quietly took them off. He resumed his investigation of what was up my skirt and was happily pleased with the result once the shorts were gone.

I had three beers. Three beers and me when I haven’t been drinking often is a bad combination. That, coupled with how wet he made me, was not a superb situation. He would also be ninja like when he saw the waiter coming to check on us; he’d quickly move his fingers out of my pussy and into either his mouth or on to my lips. Though, I didn’t mind that part at all, come to think about it, but I did like the privacy.

After the movie I must have seemed like I needed assistance; he offered to take me to his place so I could sober up. I drunkenly added “on your cock? Let’s do it!” As I stumbled out (he walked just fine), he knew people there. At the theater. Chilling. I left his side to go put my shorts back on. In the bathroom, I not only felt like a mess, I was a mess; I had actually put make up on that was now all awkward, I had gotten my juices down my knee and all over my dress. Taking a deep breath, I did my best to clean myself with my shorts and then stuffed them back in my purse; yeah…my purse smelt like my vagina for awhile. My cats loved that.


When I came out, Tony Stark was still chatting with his friends. I felt awkward as I walked up next to him; I basically stood behind him like a child until he introduced me to them. He scolded me later with a ruler for not being outgoing and being more socially awkward than normal. They were incredibly nice to me and didn’t seem to judge the fact that I looked like a drunk Vegas girl.

Tony Stark lead me out to his car, carefully I might add since apparently being physically and mentally exhausted makes me drunk at three beers. He drove me back to his place. While in his car, which was a foreign hatchback, I asked if it was alright I met his friends. Reassuringly, he told me that everything was fine; those two friends aren’t into gossip or anything of that nature. I wasn’t concerned about myself, but more that he was ok being seen with me. He gave me a look, and I felt childish for asking that. Other than Batman, I had never met one of my bed buddy’s friends. Ever. Perfect Baggage was infuriated when I asked to once, so I had a bad perception of myself and that it was never allowed. Ever.

Tony Stark and I had sex; nothing ridiculous since we were both slightly tired and I was drunk, and then he took me back to get my car when I was sober. He was nothing but a gentleman, minus the whole fingering me in public part.

Lessons learned: I deserve to be seen in public with people, especially if I’ve had their cock in my mouth. I need to have a bit more self esteem and value myself a bit better.


The Daring Vagina

This is Why Baggage Sucks…Pt 2

You can read about Part 1 here,This is Why Baggage Sucks…Pt. 1

Hate Sex is Full of Hate and Porn…
Perfect Baggage wanted to come over one Saturday after he went cave diving or something. I told him that he could for awhile. When he got to my place, my cats wanted nothing to do with him and ran away. Cats are smart; they know when people are dicks. Anyways, he wanted to have fun with my toy chest. I have so many toys, and different kinds. My porn collection rivals the big box of porn from 40 year old virgin. 122929Perfect Baggage wanted to use a dildo on me to stretch me out and watch some porn together. Well, my taste in porn is not the same as his (or apparently any other man I sleep with now that I think about it), and he wasn’t as excited by it as I was. Oh well. Also, what is with the fascination of stretching vaginas? I don’t get it…

So, Perfect Baggage and I have always talked while we were fucking. Not just, harder, faster, move that way, but things like, you watch Dexter? Well, while a Sasha Grey scene was playing in the background, Perfect Baggage decided to tell me that he had taken her with him to that God damn cave crap. I lost it. I started hitting his chest while he was fucking me. He “hugged” me while fucking me, telling me to stop struggling and to stop being mad. Don NOT tell a woman how to feel. He told me to cum; what was wrong with him? I told him no while shaking my head. He obviously wasn’t going to stop; I was emotionally done with him right then. After a few minutes, I wanted him off of me; I made my vaginal muscles tighten to mimic an orgasm so he would stop. I pushed him off of me and turned on my side and curled up in a ball. That was the meanest thing someone has ever said to me during sex, or about sex. Who would ever think that was acceptable? Perfect Baggage, that’s who. After he cleaned up, he sat on my bed and put a hand on my shoulder, trying to comfort me by telling me that he didn’t think she wanted a relationship. Because saying that makes it better? I was so upset; I led him to believe I was ok. I wasn’t. Not by a long shot. He left, telling me that he still didn’t think it would work with her and that I shouldn’t let it bother me. What a Perfect Douche.

I turned the porn off and resumed the fetal position. I’m glad I collect stuffed animals (hint hint if you ever want to get me a present 😉 ) because I cuddled the fuck out of an Alice Cooper bear. At this time I was seeing Tony Stark. I texted him to see if he was busy and if I could come over. It was the day he was moving, so, I did get to see him, and he did lift my spirits up. That man has no idea how much of a positive influence he had on my life.

Until next time,

The Daring Vagina

This is Why Baggage Sucks…Pt. 1

This is the first of three posts detailing the end of my fun bed times with Perfect Baggage. While I should have put them all together, this took a lot of emotion, so, three stories!

Like I mentioned previously, even though Perfect Baggage destroyed me emotionally, Goals, Friendships, and Those Fucking Spurs, I still slept with him three more times. I distinctly remember the three times, mostly because one rendered me spankings from Tony Stark for being late, the whole “I’m lonely and need you since she’s done with me” sex, and another was hate sex.

I’m lonely and need you…
Men are never really lonely. Perfect Baggage told me that he wasn’t seeing that girl anymore, or rather, she wasn’t seeing him anymore. My iud was still causing me to bleed at this point, but he wanted sex and I really did too. So, remembering how I “bloodied” his pillow from before, I brought my black towel over. Let me stress how ridiculous it is that he only owned white towels, even for going outside. Why wouldn’t you own multiple colored towels? He even insisted that I bring a dark towel over. Oh well. It was ok sex; I know I was emotionally hurt by him at this point and it was just sex. I want to blame the hormones as to why I slept with him. Makes sense, right? Well, during sex, he didn’t kiss me, which only angered me (I loooove kissing and someone playing with my hair), which just made me question why my vagina was good enough for his cock but my mouth wasn’t good enough to kiss. He also immediately got up and out of bed right after he came and showered. Normally, he would get us both water after the first round, but I guess he needed water all over his body instead. No matter, I knew how to get my own drink. I checked the bed for blood (blood free.)

Perfect Baggage and I had gotten into a routine after sex; I’d take a shower and then we’d talk in his living room. All he talked about was her. Her. Her. Her! I feel like Jan from the Brady Bunch right now, but it was ALL about what be did or should have done.

Well, as a lifelong Jan, maybe I DO know EVERYTHING about the world!

Well, as a lifelong Jan, maybe I DO know EVERYTHING…nah, probably not.

I could not have cared less; it was one of the few times I was ok with leaving after one round of sex. I used the excuse of cramps. Oh those pesky cramps! I’m sure I’m not alone in using cramps as an excuse to not have sex.

Perfect Baggage obviously didn’t sense how upset he made me; his constant advice asking made me feel like a high end prostitute. But at least they got paid to hear whining and to give their personal advice. What did I get? Sex with lackluster pillow talk and being all weird as fuck when I got home. “Why do you have a towel?” “Oh you know…towel things.” Yeah…I just hid the non-bloodied towel behind me and then on my side until I got into my bedroom where I could just curl up in a ball and cry.

Until the next post,

The Daring Vagina