Author: DesperatelyShy

The Virgin’s Dog Tags [FM][pic]

When I was a Junior in high school, one of my closest friends moved away. Apparently, he’d been interested in me for quite some time, but I was completely oblivious to the fact. This was normal for me and had nothing to do with him. For whatever reason, I never picked up on those sorts of things. It was probably because usually I just wasn’t interested in things going any further with anyone. Dating, romance, and especially sex were just not things that were on my to-do list. He was a little bit of a goofball and was too nervous to actually tell me how he felt before he left. I was shy, quiet, awkward, and nerdy. Sure, he was my friend, but I didn’t think we had enough in common for a relationship to even be seriously considered.

Everything changed a few years later when he told me he’d joined the Navy. He was going to be gone soon, and for a very long time. That simple fact made me want him closer. I had finally at some point realized that I did have an interest in him when we were in school together, but dismissed it since I had never dated and he had shown no signs of wanting anything more anyway. I guess the realization that he was leaving also pushed him to finally tell me how he felt. I don’t recall the exact conversation anymore, but I do remember it being clumsy and awkward on both ends. Read more »

Teased and Dominated [MF]

I secretly have a crush on my best friend. I won’t go into that much here, but I will tell you that she is hot. She’s a funny, caring, geeky, beautiful, blonde with a great personality. We’ve been friends since we were eleven and I just haven’t been able to confess to her at any point in the last decade or so how I feel. She’s been with the same guy for at least six years now and as far as I know is completely straight so to avoid ruining the friendship, I keep my mouth shut. At least, when I’m around her…

One night, I confessed to my boyfriend how attracted I was to her. He was interested, asking if I’d ever do anything sexual with her given the chance. Being a bit shy about the topic, I clammed up. It became pretty obvious that I would leap at the chance to get into bed with her. Greatly amused, and I think slightly turned on, my boyfriend has used this bit of information to get me worked up a couple times. Had I known I was going to start hanging out with this friend a few times a week as opposed to once a month (busy schedules cleared up a bit), I would **never** have told him about it. Read more »

Discovering my Newest Weaknesses [MF]

I still remember my first time. I remember losing my virginity in a cheap hotel room out of state and away from home. I remember not really wanting to lose my virginity that night, but not having the courage to say no. Since then, it’s been hard for me to know who I am sexually. It wasn’t a violent night or anything. Nothing to really dwell on, but it wasn’t that enjoyable either. I’ve since moved on and found that I quite thoroughly enjoy being with someone in such an intimate way.

Society tells us that as women, it’s not okay to be sexually open. You shouldn’t want those things. Well fuck society because I definitely want those things. My libido is ridiculously high and I’ve considered seeing some sort of sex therapist about it more than once. Who would have guessed that by the time I turned 23 my thoughts on sex would have changed so drastically from that hesitant 18-year-old I had been in the beginning. I definitely didn’t. Now I’m the one who wants to do the crazy things. I’m shy and nerdy most of the time. I even struggle to talk to people I’ve known for years. Get me in the bedroom though and if I lose myself in the moment, I’m a totally different person. Read more »

Girl’s Night [FF]

I don’t normally care to write erotic *fiction,* but I had this incredibly vivid dream that I just can’t get out of my head. I remember this cute, petite blonde sitting cross-legged next to me on my old futon, which was folded into a couch. It seemed like we were having a great evening because the two of us were cackling over whatever funny thing must have happened on tv. Honestly, I didn’t realize any of this was a dream until I woke up. It was so real to me that I could feel the good vibes and excited energy that swirled around the room and I genuinely felt I knew this Stephanie person. I turned, starting to say something, and her bright smile caught my eye. Before I realized it, my eyes were wandering. First to her pale neck, scanning over her collar bone, and then down towards her slightly revealed cleavage. She was wearing a thin powder-blue tank top and tight denim shorts. I hadn’t noticed before, but it showed off her tiny figure well. My eyes started to work their way back up to her face, noting how soft and shiny her light-blonde braid of hair looked. She looked over as my eyes met hers. I quickly looked away, refocusing on the television across the room and tried to deflect the awkwardness with a joke about our show. It worked. Read more »

First Threesome [FMM]

Of course. I finally find a prospect for the threesome I’ve wanted for a while now and it’s one of my employees. I can’t become involved with someone when I’m their boss, yet there I was finding myself much past involved. I was never a very confident flirt, but I guess there’s always exceptions. I felt like I *needed* this. I guess maybe I did. Either way it happened and honestly I don’t regret it at all.

I remember being introduced to the new guy at work ages ago. He was “new,” as in he had worked there before me and left for a while. I was annoyed at the pointless introduction. “Hey, come meet Derek.” Ugh. I said hi and wandered off to ignore the guy. I wasn’t interested in meeting new people. As a manager maybe I should have been a bit more friendly, but it just wasn’t my thing. Eventually, Derek and I ended up being friends though. Things were pretty simple between us. We gamed online after work sometimes. He gave me rides to work when needed. It was nice to have an easy friendship for once. Read more »

Somnophilia [MF]

*This story is about two years old now I think. If anyone has any concerns regarding the content I will happily elaborate on the less fun/sexy details.*

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My relationship is the most sexually backwards relationship I have ever heard of. It’s actually me who wants sex, a 23-year-old female with short brown hair, a pretty average build, and what I’ve been told are a “very perky, fantastic” set of C’s. Meanwhile, my 23-year-old boyfriend is content with once a month or less even though I regularly pursue him. It’s the one thing about our relationship that I genuinely hate. Everything else is great. We match so well in every department except for our sex drives. When it does happen though, boy does it make up for the wait. Read more »

[F]irst time cli[m]axing from choking

|*Not a very recent story, but I hope you all enjoy!

If you want to avoid some spoilers (albeit small) I don’t recommend reading the rest of this paragraph. However if you want to understand a little bit of background before you read, this should help. I usually leave this part out because I feel like I already have so much build up and this is supposed to be a sexy story. Conversations of rules and boundaries are not fun and sexy. They aren’t interesting, but they are important. Prior to this story, my boyfriend and I had discussed that I have a fetish where I like to play with him while he’s asleep. He and I set one major rule along with some general boundaries. That rule is that there will be no actual vaginal penetration. He also has permission do the same things to me while I’m asleep with a similar set of rules.*

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Tortured for information [MF]

|*Now that I have a NSFW account I’m moving all of my content over here. This was one I had posted a few years ago. I hope you all enjoy~*

I’ll start by explaining that I’ve had A LOT of trouble sleeping lately. Most nights I find myself wishing I could just get my brain to shut up. Eventually, I end up sifting through all of the most terrible thoughts I have shoved in the back of my head. I get more and more upset until I’m fighting sleep because I’m just so depressed/panicked/unstable that for some reason this makes sense to me. My boyfriend and I live together and he’s been concerned about the lack of overall sleep I’ve been getting. I had already told him I didn’t want to talk about what was upsetting me (it was the past and I really didn’t want to bring it up and make a problem where there didn’t need to be one), but he was insisting on me telling him what was going on. I knew that I needed to get it off my chest, still though, I decided I’d rather not share with him since he had to be up early. I wasn’t sure how the conversation would go and felt it would be best for another time. Apparently, he had other plans. He decided that he was ABSOLUTELY going to get me to spill the details. Read more »