So You Like Tats…

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Remember how some of the best Christmas gifts came in small packages? Well, some of the biggest penises hang on some short as fuck men. This guy, Tats Man, was like 5’7 on a good day in shoes (I’m 5’9 on a bad day in flats), super skinny, slightly greasy and shoulder length black hair, light skinned Hispanic, and COVERED in tattoos. When I say covered, I mean covered. Some he designed and gave himself, and some he let people give him when they were working on building their portfolio. His array of tattoos was probably a great fit since he did work at a tattoo supply store.

When Tats Man replied to my ad, he gave me his number (along with some awesome pictures of himself.) As I was feeling adventurous and daring that morning (work was super boring at the time), I decided to text him with a “you shouldn’t give your number out to strangers, what if I was a creeper?” Of which he replied “You won’t be a stranger much longer lol.” Yeah, I was fairly happy I texted him.

I sent him an array of pictures (including some of those provocative ones I took for Joker.) When I say array, I mean months old to a few hours old pictures. He pointed out that I looked different between them–not in a bad way, but “stunningly different.” Tats Man told me I was beautiful and he wanted to at least meet me, no sex needed. Now, in case you haven’t figured out my personality, I have a lower self-esteem than most girls; I was rarely hit on or called beautiful by like any men (my partner tells me it’s implied.) I was blushing up a storm in my tiny office. We texted a lot and about the most random things. I even told him about my partner without him needing to ask. Though, he did ask why I was still with him and if I knew why he didn’t like sex. I feel that if I knew…I would probably have tried to fix it. We were texting one Saturday when I had a major event for work and he invited me to come see him at work once I was done. I told him I would be exhausted and he said he would get me a chair to sit in at the store. He just wanted to see me.

Tats Man was working at a tattoo supply store fairly far away from where I lived at. Up until then, I had no idea that the equivalent of a Sally’s existed for tattoo supplies. When I got there, Tats Man was working with a customer, so I just walked around the little “U” shaped store, looking at the different tattoo supplies like ink and needles. He had the biggest grin when he saw me and gave me a really awkward wave. He continued to help the customer a bit before coming over to see me. Tats Man gave me a hug and just stared at me for what felt like an eternity (like a grandparent does after months of not seeing you.) He then said that my pictures didnt do me any justice; I looked even more beautiful in person. I was putty in his hands. We small talked a bit before he had to check the customer out. When he came back, we talked extensively about sex (he suggested we even go into the back storage area; I’m not that horny.) The talk eventually turned to when and where will we get to have sex, so I told him about my partner’s schedule. I stayed for awhile before I was just exhausted and needed to leave. In that time span, a few customers came and went and I learned a lot a about tattoos, that’s for sure.

Tats Man came over to my place one Saturday before he had to go in for work. I told my partner to call me before he came home from work (he’d been leaving work really early a lot lately.) We talked, he felt up my boobs and then tried to see if they were bigger than his face (they kinda were.) Tats Man was there maybe an hour before my partner called. Pussy blocked…ugh. We set up another time during the week when I could get away during lunch and he was off.

I wore a cute dress that day since I knew I’d see Tats Man. I got home, made a quick lunch, and slightly undressed. When he got there we got right to it. Tats Man’s penis was as big as his forearm, good Lord. I thoroughly enjoyed giving him head because of it. For someone so tiny, I was amazed his cock wasn’t classified as a third leg. I warn every man that my vagina gets incredibly wet (no, I don’t squirt), and Tats Man was still amazed with how wet I was without any sort of foreplay. What can I say? I love the anticipation. He enjoyed going down on me immensely. When Tats Man put his cock in, he immediately took it out, telling me he was going to cum way too soon. Personally, I have never seen the problem with a guy cumming quick; you obviously have an awesome pussy. I told him out was not a big deal; it meant we had a starting point to work from….and we definitely did.

We texted on and off, met up a few times and even hung out (he is a legit artist and I once went to his art show to see his work.) In all honesty, I made a pretty awesome friend. He did get a girlfriend (she let him tattoo the fuck out of her) and I had to find a new bed buddy. So the search continued for the best friend with benefits around.

Until Next Time,

The Daring Vagina

Amazing Sex is Damn Good

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Out of the men I met or talked to from my first post, the first guy I slept with, lets keep with the comic book theme and call him the “Joker” since he had an amazing smile, was a great starter to meet. He was fit, curly black hair, beautiful green eyes that I was mesmerized by, under 30, and he wasn’t a Grade A moron. After a few e-mails, we exchanged numbers. I am not one to take flattering pictures, let alone naked flattering pics. He would ask to see me bent over (hardest pic EVER to take!) or me licking/sucking my own nipples. I would just respond with a “…well ok…” and send something. SIDE NOTE: Do NOT take nude photos of yourself with your face fully visible unless you’re really ok with them being everywhere and anyone seeing them…like his buddies that could be acquaintances of yours. I am so confused when anyone does that. Don’t make a sex video that includes your face or very easily recognizable tattoos either. Be smart. He asked what I was into sexually, what my fantasies were, and then he asked the dreaded, “are you single?” I explained as best I could that I was in a sexless relationship but I would never ever leave. He was ok with that, which surprised me. 

At the time, my partner was still working until 9 most evenings (giving me plenty of wiggle room for play time) and I got off work early every Friday. One Friday, Joker texted me, saying he had some free time to meet up if I was available. I’m the type of person that will leave a damn funeral for sex. When he texted me, I was coming back from the mall with my friend and basically squealed with excitement in her passenger seat. I was about to have sex with someone that I handpicked for my vagina; I won the man jackpot!!

Let me describe my place so you can imagine the layout better. One bedroom/one bath upstairs apartment, spacious bedroom with a queen sized bed, tv in the bedroom, two computers in the living room, and two scaredy cats that would never come out. With two people living in a slightly cramped apartment, it gets cluttered easily. When I got home, I hastily made the bed, tidied up the bathroom, lit some smelly good candles and put on just a t-shirt and athletic shorts. And then I anxiously awaited his penis. I turned the tv on, relaxed and almost took a nap by the time there was a knock on the door.

I could feel my excitement hit a high peak before I even opened the door. He didn’t even need to be there to get my vagina ready; he could have skipped any foreplay right then. When I did open the door, there stood my ideal man. Joker was maybe 5’10, super tan, had beautiful Irish green eyes and black hair. He was a crew lead (or something like that) for a construction company and had a solid farmer tan. His hair was a bit shaggy underneath his baseball cap that looked just as worn out as his steel toe boots. I offered for him to come in and if he wanted anything to drink. We made our way to the bedroom where we talked for a bit before we both felt comfortable enough to start removing clothes, starting with his boots and shirt. 
Joker was a great kisser, and he knew exactly what he was doing as far as his hands were concerned. He had that terrible tan, but I had no problem seeing past that to his amazing arm muscles. Joker was an expert at putting me where he wanted me on the bed, and luckily was nowhere near a minute man (thank God for that.) He was rough–sometimes a little too rough—-and very thick (doggy was a tad bit painful when he picked up his pace too quickly.) I can safely say that after he was done with me (which wore us both out), he was in the top three fucks. Ever. His overall style was dominant, but he was a pleaser and kept asking what it would take to get me to cum (wouldn’t he have liked to know.)

Joker only came over one other time (his work schedule didn’t always mesh with my availability), and it took all of me closing the door for him to go primal and try and pick me up (I am fairly fat) and fuck me on my awkward couch right by the door. It did probably help that I was wearing very flattering lingerie when I opened the door. We kept in contact for awhile, but we had long-term, conflicting schedules. But he was always good for getting my motor running with some imaginative texts 😉

Sincerely,

The Daring Vagina

So Many Dick Pics…

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By this time in my craigslist adventures, I had read and responded to a lot of postings, but I had never created one of my own. I mean, I know what I want and looking at all of the short posts with obviously old pictures (yeah…no one is going to believe you still have that computer from the 90s and use it…get a better pic), terrible grammar, and the lack of replies was making me sad. Were there really only a handful of men in a large city (a few million, give or take) that would sleep with me? I decided that couldn’t be true. I needed to write …my own posting. 

I am a perfectionist and a planner; I needed to see my competition and then work up the ULTIMATE POSTING! I perused the W4M section; there were like…none. The postings were short, illiterate, and incomprehensible; the ones with pics had descriptions that didn’t even accurately describe what was in the image. Don’t say you’re black when the girl in the picture is not only pale but a ginger. The majority of these ads were 4 sentences long, talking about how they needed a “big dix” to “fuk al nite.” I finally got why men kept talking about spam and bots; the whole w4m section was full of that crap. After my analysis, I was ready to piece together my perfect ad. 

I told myself no pictures, be me (sarcastic and awkward), and say exactly what I’m looking for (a long term friend with benefits, or fwb.) I started out describing what I wanted: someone who could come in, bend me over the couch, fuck me, and then have an intelligent conversation. I needed to connect with them enough that I’d see them often. Then I described myself physically and personality wise. I made sure to include that I was ddf (drug and disease free) and that I was going to stay that way. I never said I was single or in a relationship; I wanted to avoid that subject at all costs. After the little spiel about myself, I talked about the type of guy I wanted: a sane guy for craigslist standards, intelligent, fun, drama free, and ddf. I then closed it with my all-time favorite online pick-up line: tell me a little more about yourself, and send a pic, and I’ll return the favor; I’ve been told I look good with a cock in my mouth 😉 

I was not prepared for the amount of responses, the dick pics, or how to tell someone thanks but you’re not attractive to me and I’m not that desperate. I was in my early twenties, I didn’t need someone that was 50; I may have daddy issues, but not like that. I took my time going through each reply; there were quite a few good ones. Some men would reply with just “R u real ?” and that’s it. I would reply with yes and they would then ask for a pic; I would tell them that’s not how it works and they would get angry. Oh well…should follow directions. There were plenty of other guys that not only did, but were way too hot for me.

Many of the replies were full of so many grammatical errors…it just hurt my brain. I didn’t care how hot, no go!  With every response that I was interested in I replied with a pic and more about myself. I always asked what they were looking for and if they could host at their place (how to weed out the people living in their parent’s basement.) I figured it would be best to play out the different men to see what would happen.

My post was eventually flagged as spam; I was extremely offended that someone would say I was a bot, and I went to see what I could do to un-flag myself. For the record, you can’t. But you can just keep reposting it and say “I’m real, stop flagging meeeee” like half the men do. I also imagine they’re pouting about having to copy and paste (life is soooo hard.) My post was up for a solid 5 hours, maybe 6. A lot of responses had men saying it was refreshing to have a real woman post and how much they enjoyed reading what I wrote. I’d always respond with a thank you. Even if we weren’t each other’s type, it was a pretty good compliment. Who doesn’t like praise over something they’ve done?

From this posting alone, I was able to find a few good men to possibly bend me over my couch. Each man was my “type” in a sense; thinner and taller than me, intelligent enough, and really easy on the eyes. From my efforts, I was able to sleep with a few men. I did post another ad not too long after, just to see if I could get different men (I did and then I got the same shitty pictures and dumb responses too.) It was a new rush; how many men out of my league would call me hot and want to sleep with me? More than you could possibly imagine…

Until Next Time,

The Daring Vagina

The Dark Knight’s Friend: Robin, Boy Wonder

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I know I’m guilty of kissing and telling, but I’ve never tried to give that person’s contact information away to a girlfriend so she could get laid. Well, Dark Knight did just that.

I was catching up on my 40+ hours of DVR backlog one night when I got the most random e-mail. A guy who claimed to be Dark Knight’s friend, let’s call him Robin, said that Dark Knight had told him about me and now Robin would love to “get together” sometime so we could “do stuff.” This was all because Dark Knight had told him about how fun I was and that I was “so chill.” To put it nicely, I was livid at the situation. I smashed my fingers on my phone to type up an e-mail to Dark Knight, asking him why the hell would he talk about me like that, let alone give a stranger my contact information. 

After about 10 minutes of silently fuming to myself, I reflected on the fact that someone just talked the fuck out of my sex skills. He did so well at it that someone who had never seen nor met me wanted to sleep with me. I don’t know what I was actually thinking, but I decided I would reply to Boy Wonder’s e-mail. What’s the harm in e-mailing someone…right? After a few emails in which we exchanged pictures, we exchanged phone numbers so we could text (at least he had a phone.) At least he texted often and wasn’t obscenely vulgar.

When we finally got together, Robin talked constantly about Dark Knight; what they did together for fun, how they’re basically the Flight of the Conchords and how he is so lost without him. I felt like a therapist. Robin kept playing the pity card since Dark Knight was off at basic training; he kept referencing how he was all sad and lonely…and horny. 

Meeting Robin in the flesh was an experience in itself; he was a bonafide hippie if I ever saw one. If his hair could have been long, it would have been. Thank God his job made him keep it short (he was a cook.) He talked like a surfer dude (very slow and drawn out), smoked pot and offered me hits constantly. He was fairly tall, about 6 foot, with a creepy 70s ‘stache, blonde hair, blue eyes, average build with a growing beer belly (not like I’m one to talk), and owned a colorful fish that he called his baby. He would take hits from his bong and then he would make out with the fish through the glass of her aquarium. He cooked at a retirement home and would always offer me leftovers when I came; he said that he learned all of his cooking skills from Dark Knight when they lived together on the coast. 

It did not take Robin long to get down to business. I have never detested aggressive sex, but he was the first person into the most out there sex acts I had let fuck me. Ever. For specifics, he was into way degrading and humiliating sex acts to women. He had a decent sized (well, pretty long and somewhat thick) cock that he enjoyed making me gag on or slapping my face with. He tried to spit on my face once. Never again. He refused to even touch my pussy. With his kissing skills, I would have insisted he stopped immediately; it was like he was sucking the life out of me, Hocus Pocus style. He never lasted long, and when he actually was able to have anal sex with me–which he’d still do after my protests–he lasted maybe 3 minutes. At least he was able to cum a few times in a night. Every time after he came, he needed to go outside and smoke a cigarette. He went on his porch because they were “so much worse than weed” and he couldn’t stand the smell.

I came over quite a few times even though I didn’t enjoy the sex all that much (I needed the mental escape from work, badly), nor did I enjoy his company. Eventually we just stopped texting. After awhile, I received a surprising email from none other than the Dark Knight himself (he did apologize for what he did with giving my information to Robin and hoped I would forgive him. I did make him drag out his forgiveness with constant sorrys; I need to make sure men know I’m the controlling one in a sexual relationship.) I was actually excited! He wanted to get together because he had some time and we planned everything out…and then my partner was home from work. We went to Plan B: Go to Robin’s place because he shouldn’t be there. 

Well, what do you know? Robin was there. Dark Knight was like, well…still want to have sex here? I had already shaved and was not about to pass up on long lasting sex. I finally got to have sex on Robin’s bed–small victory! Dark Knight did his best to prolong his orgasm, much like last time, and I became slightly bored with the same two positions (I hate being on top)…

Once we were done, I cleaned myself up and left. Robin was sitting where we left him in the living room on the floor, eating some leftover hamburgers he had repurposed into monstrous burgers. It took months before I heard from Dark Knight again (busy with basic training and shit.) However, Robin wanted to continue to “hang out” with me. I agreed that we should hang out again; we both wanted sex and it was fun exploring my deviant side. I did see him in-between my quest to find the perfect friend with benefits. Alas, we will start that journey in the next post. 

Sincerely,
The Daring Vagina

The First Mistake is Always the Worst

I was lonely; Dark Knight was gone and I was horny. Vibrators weren’t cutting it anymore. I decided to browse the personals, seeing if any decent sounding guy was into BBWs. I saw a posting that seemed ok. I replied to his ad; I attached a picture and privided a little description of myself. He immediately replied; he, let’s call him “First Mistake,” gave me his number and told me to text him. Being still naive to craigslist, I did just that. It was fairly late on a Saturday night. He kept asking me to come over; I told him it was too late and maybe I could come by the next morning or afternoon.

When he was giving me directions, he asked if I had a vehicle or needed the bus route information to the place he was living at. I was like, uh no…I have a car. First Mistake decided to tell me everything about his living situation and past experiences…once I got there and then AFTER we had sex. He lived in a rehab house with 6 other men because he had been homeless and living on the streets for a few months. I associate most homelessness with veterans and not with what he finally decided to tell me. After we had sex, he then told me he used to be addicted to all sorts of hard drugs, like heroin. I just sat there and was like…oh, that’s cool…glad you’re clean? This is why condoms are ESSENTIAL. 

So, to describe First Mistake, he was stocky, in his early 30s or so, a few inches taller than me, a quick cummer, and he had a disappointingly average penis. He enjoyed going down on me, which was a pleasant first from the men of craigslist.

After learning everything about First Mistake’s life decisions, the minute I was out of sight I deleted his number and never responded to his texts. I went and immediately got tested for everything under the sun (all negative, thank God.) Lesson learned: Always properly screen your potential bedroom buddies. ALWAYS.

Sincerely,

The Daring Vagina

Friendly Drunks Are Disappointing in Bed

As an adult it is so hard to find friends outside of work. In college, you get new friends (or possible friends if you aren’t an asshole) every time you take a new class. But once you’re out of school, where do you find new friends? Especially if you aren’t the barsy type…or hangout with coworkers…or you move to a new city. 

I originally used craigslist for the strictly platonic section. I wanted a friend to text with (I am permanently attached to my phone) and hangout with at times. At one point in time, I had replied to someone’s ad who was looking for a friend. They had an awesome storm trooper helmet in their ad! How could I resist? He seemed normal for me; we liked the same things, and he wasn’t a gossiping bitch (no offense to the gossiping non-bitches.) I met him, let’s call him “Friendly Drunk,” for lunch once. It was actually fun for me; I don’t like people and I had fun! He mentioned he needed to do laundry, so I invited him over to use mine (little luxuries like having a washer and dryer in your apartment rock.) NOTHING HAPPENED because I just wanted a friend at the time. 

Flash forward a few weeks; we had been texting for awhile, and out of the blue FD invited me over to drink with him. He told me to pick up some beer and come over. I bought a 6 pack and headed over to his place. Physically, FD was shorter than me (5’7 or so), white, a bit over weight, dirty blonde hair, a bit of a nerd, and he was some kind of online tutor. His clothes smelt like they were old and had definitely seen better days. His place was such a mess that even the most experienced maid wouldn’t want to deal with his clutter. The living room consisted of two bean bag chairs (one with a hole) and a small tv. FD was already drunk (or very tipsy) when I finally found his place. He took my 6 pack and was sad because that was all that I brought. He begrudingly offered me one of my beers and we sat down to just talk. Before I realized it, the 6 pack was gone. Kudos to him for being a really fast drinker and slightly functional alcoholic. 

In his drunken stupor, he decided to make  a move; I wasnt expecting it, but I didn’t really resist it either. But now I know drunks can be really forward; he went to town fondling me like a high schooler, but he was experienced enough to undo my bra with just one hand while beneath my blouse. He kept trying to push on the back of my head to get me to, I guess,use my mouth to undo his pants. I have some strong muscles and easily resisted. When he stopped and eventually undid his own pants, I was more surprised than anything; he had a Prince Albert. I was intrigued enough by it to play with the piercing itself for a long time before actually going full out blow job mode.

As im sure many of you have sadly experienced in your life, drunks aren’t amazing at sex. Friendly Drunk passed out not once but twice while I was giving him head. He was also very awkward at letting me do what I was sure would actually get him off. After the first pass out, I woke him up and he magically got hard again. Me made out for a bit, he pushed my head down to his very average size penis, and passed out again after maybe 7 minutes. After the second time, I was infuriated that not only was I wasting my skills on someone who wouldn’t remember what happened, but I was getting nothing in return. After waking him up for the second time, I told him I was going to just go and he walked me out to my car. 

About a week later he texted me to hang out again. I asked if he was going to be drunk and pass out on me again. He replied with: I guess not. And that’s how I got rid of my first overall disappointing experience.

Sincerely,
The Daring Vagina

The Dark Knight Did Rise

After my initial success with “First,” I wanted more. I wanted a partner that was more adventurous in bed, more attractive, and that I could be with more times a week. I just wanted more. While browsing the ads on Craigslist, I saw an ad for someone younger than me and who lived outside of the city. Because I don’t mind driving, and his pictures that he posted made him to be almost a dream guy physically, I decided to reply. I mean, his ad did say he was great at massages, and I so needed one. I gave my spiel on how I wasn’t getting sex at home and included some of my better pictures. Let’s call this guy “Batman.” Batman was maybe an inch taller than me , so around 5’9, wore Buddy Holly glasses, tanned white guy, a year behind me grade wise, and had a stoner approach to things. Batman responded back that he was interested and we corresponded for a few days over what we liked sexually, what we were looking for, personality traits, etc. He even told me how he was training so he could survive boot camp for the Air Force. But then, Batman just stopped responding. I was actually sad; he was dorky, cute, and fit. A week or more had gone by and I decided to browse the penis pic filled M4W section. Low and behold, I saw a new ad of his, with the same pictures from the previous ad! Being slightly miffed, I sent a not so concerned reply to his ad, telling him that he should have told me he wasn’t interested in meeting me. However, that was not the case; he was “scared” and got cold feet. Nevertheless, I wanted to give him another chance.

When I asked to exchange numbers to text him because it would be easier, he let me know that he didn’t have a cell phone. I was perplexed more than any sort of red flags going up in the back of my head. So, we continued to correspond until we decided on a day that worked for both of us for him to come to my place. Thus, I gave him my address so he could come over (when my partner was supposed to be at work.) Hours passed and he never showed up. I sent him an e-mail, pretending to be concerned even though I was enraged that I had shaved my vagina to be stood up. Again. When he finally was able to e-mail me, he had somehow wound up at the wrong complex (there are multiple surrounding complexes by me.) He said he still wanted to meet up, so we found another day, and armed with super detailed instructions, he was to come over. We had picked a time when my partner was supposed to be at work, but he left very early. So early in fact that I was not able to e-mail Batman about my partner being home. When he showed up, I gave him an “Oh God, my boyfriend is here…oops” look. We played it off really well; I feel I deserve an acting award for that. Maybe an Emmy (it wasn’t Oscar worthy.) I told my partner that Batman and I were going to watch Dark Knight because he hadn’t seen it (and because the TV was only in the bedroom while the computer and video games my partner was occupying was in the living room.) I told my partner we were going to close the bedroom door so he wouldn’t have to hear the movie.

The door was closed before he gave me a much needed, though sometimes rough massage, in which he worked his way below the belt and up my loose fitting shorts. Batman’s sex was prolonged; he mentioned time and time again that it had been months for him and he didn’t want to climax early. He had to keep his glasses on the whole time. In his ad, he had mentioned how much he loved giving oral. Though when it came down to it, all he wanted was to receive it. Much like First, he had a painfully slow, and rhythmic pace. Considering how careful we had to be with my partner in the next room, we could only do one safe position–that way we could switch out of it without it looking like much. He was very aloof and lost; he still had the feel of someone that was a freshman in college even though he was 22. It took a good portion of the movie and then some for him to actually follow through and have sex. I am sure the rush of having someone on the other side of the wall was a rush for him, but it also made him nervous. I had to keep giving him oral to keep him hard. Batman did finally orgasm; he was quiet and kept thanking me for everything (the oral, the sex, the drink—everything.) I told him to let me know when he made it home and if he had time before boot camp to let me know.

 

Batman will return…