Self Care and Blurred Lines: Dee

One of the most frequently asked questions from my email group is "Have you ever slept with Cassidy/Are you going to share that story?" I always answer the same way, we are just friends but its complicated. Our friendship is one of blurred lines and this story will highlight that a bit. This story I have never shared with the email group mostly because some things should be a mystery. I am sharing it here because I wanted to surprise Dee. She usually gets my stories ahead of time but this one will post without warning and will be about her. Just because I like keeping you guessing girl. Enjoy.

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Soon after becoming sexually active my masturbation habits went through the roof. I was constantly trying to explore my body and find new ways to stimulate myself. I watched and read porn almost as much as I did any regular reading. I spent most days in a haze of sexual energy from edging, teasing and my newfound hobby online role playing. I managed to find a few people who enjoyed crafting stories out of ideas with the most basic of framework and expand on it as we each took turns sending each other paragraph's of the story. It was insane how much time I spent crafting those words and waiting for responses.

One of those stories an anonymous internet "friend" and I worked on involved two sisters that enjoyed a game of masturbating in risky places trying to out do the other. I will admit it was a bit on the taboo side of the house but it was all fictional so why not. During my day I found myself wondering where my character would get off next to out do her equally adventurous sister. It didn't take long before my imagination stopped showing the made up character and it showed me doing this risky public pleasure sessions which led me to ask myself if I really wanted to try it.

Of course I did, but lets be real here getting off in church while pretending to sing in the choir wasn't quite feasible for me. The fear of getting caught was one thing but the possibility of actually getting caught terrified me. So, I shelved the idea for a while preferring to stick to the safety of my own home in my bed where I could let loose and let my fingers walk me to my destination.

A month or so later Cassidy my best friend was in town which always meant a good time. As per usual she crashed in my apartment and she forced me to engage in late nights of drinking and laughter. As an avid reader of my stories and the curator and admin for my email list she of course wanted to know what I was working on. I was exploring a lot of kinks with James while he played as my sexual Sherpa letting me figure out what I liked and didn't which made for good reading but repetitive.

"I love this James guy and I don't know why you don't let me meet him but what's next?" She poked pouring another shot.

"You don't get to meet James because I don't want things to get complicated. We aren't friends like that we just have sex a lot." I laughed feeling giggly thanks to the bourbon she picked up on her way in.

"But he likes you though, I mean its obvious right?"

I waved off her remark grabbing the shot and picking it up for a toast. She was right, he did like me but I didn't want a relationship it would have complicated my overall goal of sexual freedom. We made sure to tell each other when we had sex elsewhere and got regular checkups and I felt how weird it was the first time I turned him down for a newer partner.

"To the next thing!" She proclaimed louder than required hitting our glasses together and downing the shot.

"Do you have any sex toys?" I knew the answer or more accurately I assumed the answer but I hadn't quite let go of the idea of public masturbation and decided I might need something faster than my fingers.

She coughed a bit surprised by my question while she was focused on the chips and salsa.

"Uh duh? What kind of woman do you take me for? Don't you have some?" Her face made me feel stupid because I didn't and she saw it.

"What the hell! Seriously? Not even like a little vibe?" The amount of drama she was bringing to these simple questions was way over the top but such is my girl.

"No, not even a vibe. Sometimes I look online for some but never order anything. I don't know what half the shit does and most of it is a lot. Like why do I need ten vibration settings?"

She immediately burst into laughter bringing me along with her while we imitated jackhammer noises. Laughter turned into tears as the jokes got more and more vulgar one upping our power tool references and what it must mean about you if you needed all that to get off. When we finally calmed down remembering I lived in an apartment and had neighbors she poured another shot told me to hang on and got up heading to my room. I imagined she was just using the bathroom but she came back with her hands behind her back.

"This is one of those moments where I tell you not to get weird on me." She said sitting down awkwardly with her hands behind her back. I did in fact have a tendency to get "weird" as she put it but she shocked me so often I don't know how she expected me to react.

"Let me guess you are a jackhammer kind of girl and you have Tim the Tool Man Taylor's workbench behind you." I responded making us both erupt into laughter.

"Oh my god, ok look." She pulled a towel from behind her setting it on the floor and unrolling it revealing four phallic shaped objects with varied size and realism.

"Uhm wow that's a lot!" I said reaching for the one that looked most like a real dick before stopping.

"Are these clean Dee the builder?" I smirked to an extreme eye roll making us laugh once more.

"Yes, they are clean pick one up drama queen!"

I picked up the beige colored dick that was roughly maybe seven inches but skinny. It had veins on it and was very flexible so of course I wiggled it around in her face laughing. When she tried to swat it is when I noted the flared end under the fake set of balls.

"A suction cup, what for?"

"Haha, you can stick it to something and ride it like your floor or a wall. Personally, this one is my shower buddy." She said taking it and slapping it down on my coffee table and slapping it showing it stay secured but flop around.

I immediately pictured my friend in the shower backing up against it and against her advice as usual I got weird.

"Ok I haven't had enough to drink for this." I said averting my eyes only to end up on the other three devices in front of me.

"No, no, no How are you such a deviant and such a prude at the same time! Yes, I masturbate just like you do I just use toys girl relax!" She handed me the poured shot and we both put them back quickly and I decided to just accept this was going to happen.

"Now this one is fun and discrete, good for travel." She said picking up a smaller slim vibrator with a bit of a curve on the tip. She turned the bottom and it began to vibrate making me jump.

"See feel!" She handed it to me and it felt powerful like it would rattle my bones.

"Is this like normal or super strong?"

"Nope that's your most basic, it seems like a lot until you use it. Once it goes inside its not as loud and the vibrations feel amazing. With the end you can hit the G spot perfectly." She said making a penetrating gesture.

My over active imagination was sending me very graphic images of my friend. It made me think of her reading my stories using these toys. I was lost in thought as she explained the next two, maybe it was a fantasy. I saw her in bed with backing up on the suction cup dick while staring at her computer letting my words. I heard her explicit moans, saw her breast swaying while she rocked back and forth slowly imagining James working me over at the same pace. I felt my face heat up and my lip snug between my teeth.

"Uh earth to Belle? You ok?" Her hand in front of my face waving brought me out of my trance.

"Yeah I am cool just, I just, drank too much." I replied feeling embarrassed.

"Oh, shit don't puke on me tonight I really don't want to clean puke."

"I won't, I won't." I tried to laugh it off.

"Well...if you want to take one of these tonight like I said they are clean. In the morning we will go to a shop and get you some." She asked arching an eyebrow. I knew she wouldn't settle for no and I also knew I wouldn't use it, I couldn't. So instead I decided to challenge her.

"So, you want me to use a toy you've already cummed on, girl please." I laughed and waved her off glad she responded with laughter as well.

"You right, you right we will just pick you something up in the morning."

With that the conversation shifted, an hour later we went off to bed. Two more shots, a shower, and a whole slew of non-sexual conversations later and there I was in bed horny and thinking about Cassidy. I tried to just go to bed I really did but my body called for more. I wondered if she was on the couch using one of those toys right now. I wondered if she always did when she came to visit, why else would she bring all those toys she had to be using them. My mind drifted to her long showers, how hard it was to wake her up in the morning and how she always found excuses to take mid-day naps.

Putting the pillow over my face I tried to put the thoughts out of my mind but they kept coming back. I opened my last email I sent out to the group and re-read it playing the scene out in my head the first time James let me work on various positions of me on top. My riding skills needed work but I read my words thinking of how it felt to bounce on his dick while he moaned under me. I let my hand slip into my pajama bottoms slowly finding my clit, going over the words and enjoying the stimulation.

I got to my favorite part reading about how he came from me simply rolling my hips in his lap slowly rising and falling. How it felt to have my hands on his chest feeling his heart race while his dick spasmed inside me filling me. I loved cum and more especially loved the feeling of a man cumming inside me. I picked up the pace with my fingers meeting no resistance gliding over my clit when she popped into my mind. My brain fed me images of my best friend doing the same thing laying in bed thinking of me, wishing it was her. I imagined her on my couch writhing right then satisfying her inebriated lusts. I came immediately.

The amount of shame I felt was immense, I just got off thinking about my best friend, a woman I had known almost my whole life. I put away the story and began writing myself questions I could try to answer when I was sober, I couldn't just go to sleep without working some of this out. I ended up with five questions to get to the bottom of these feelings. Once I finished writing them down I reluctantly left the safety of a writing space, put my computer to the side and eventually passed out.

The next morning, I avoided the notepad in which I wrote the questions trying to put it all out of my mind. I did fairly well until after we ate and she proclaimed she found a store nearby we could visit to buy me some toys. I protested the idea and she of course wore me down until I was in the car and she was making up songs about me getting sex toys. I couldn't help that I was indeed curious about getting toys and I did want to have someone that knew about them to go with but her constant teasing was going to make this a nightmare.

"Look! Dee I need you to relax a bit!" I tried using my stern voice but faltered and sounded whiny.

"Ok, ok, I'm just excited helping you cultivate your inner freak is all. I will tell you what, I will chill and make this a very easy and educational trip but you have to allow me to purchase two things for you with no protests. Deal?" She parked and looked at me waiting for me to concede to her deal while I stared at the front of the store full of mannequins wearing wigs and lingerie.

"So I agree to let you buy two things that I cant have any say in or you make this a tease fest. Why are you my best friend again?" I exhaled.

"Because I slapped big Anne Jenkins in the sixth grade for making fun of your glasses." She laughed undoubtedly recalling the memory.

"Fine lets get this over with." I couldn't help but smile even though I was rolling my eyes at her. My phone started to go off as I exited the car. I pulled it out of my pocket more concerned with the outfits these plastic ladies were wearing. I considered getting one to wear for James but I didn't want him to get the wrong idea. Although it would make for a nice surprise.

I looked down at my phone as we walked in and Dee was busy greeting and subsequently shooing off the lady behind the counter. It was a reminder I didn't remember setting to work on the list from last night.Damn! Ok drunk Belle clever move. I looked up to see Dee beaming from ear to ear standing in front of a wall of skimpy outfits in plastic bags, no doubt imagining what would look good on me. Again that uncomfortable weird feeling crept over me, I exhaled and pushed it down as best I could and opened the list. The first question was simple,Are you sexually attracted to Dee?

I walked over to her and joined her staring at the wall and making remarks about what would look good on who trying to remain natural while also taking an actual look at my friend in a sexual light. I have always thought she was a beautiful woman. Physically she has the physique I would desire in a woman, she has the attitude and she has the brain to keep me interested long term hence why we are friends. Maybe an inch or so taller than me, two shades darker than me and a comfortable thickness, nobody would ever call her fat but she had ass and hips for days. Her work was very physical so that kept her in shape without having to go to the gym but the question was if I was sexually attracted to her.

We ventured around the store with her doing a remarkable job of making it less awkward explaining things and kinks she wanted to try and being vulnerable about things she was too nervous to attempt. It seems neither of us were ready for whips and chains but handcuffs seemed acceptable. Most of it was good for a laugh. Making it to the section of DVD's we scanned through titles picking things up in a mini contest of who could find the raunchiest kink. I learned very quickly I should never let my good friend see my porn history because in truth she was a bit more closed minded to things than I.

"Who still even buys DVD's? The internet is full of free porn." She said looking at the back of "Brazilian Bubble Butt volume 9."

I laughed "I mean they are still here so someone has to be making money off of them right?" I cautiously eyed a DVD themed around "cumsluts" and made a mental note to do further research or maybe come back and get the DVD. I laughed at myself,I was the type of person that would buy a DVD that had 6 straight hours of curated content!

"C'mon the toys are over here, we will take a look and then go get baskets and start shopping." Her eagerness was not lost upon me but I did like her plan of taking a lap around the store before picking things up, it gave me time to digest the things I was learning.

We made our way over to a wall that had an overwhelming amount of toys in an overwhelming amount of sizes. We both stood just staring at the various dicks and dick like shapes in front of us for a moment before the woman that worked there walked up behind us.

"Can I help you girls find anything?" She asked making us both jump and then laugh.

She was a bit older but obviously used to wide eyes and sex toys which I found entertaining. I was effectively about to buy my first sex toy from a woman that could have been my mother.

"Not quite yet actually, we are still in the "looking phase" we plan to circle back around for the "what do we actually want phase." Dee expertly handled the situation once again making me appreciate that she was here after all.

"Oh of course I completely understand, let me know if you have questions." She replied before walking back to the front of the store.

We both giggled like idiots before facing the wall again.

"Some of these are absolutely huge, like how can you take that monster thing up there and still find pleasure in sex?" I asked pointing at the "Mega Meat foot long black dick" on the wall.

"Girl I do not know, I still gotta get married one day I cant be out here all loose."

"RIGHT!" We both erupted into laughter.

We worked our way down the wall where things got more manageable and a little less intimidating. I eyed a package that was perfectly named "My first vibe" it was slim about six inches and straight. Probably the least exciting thing on the wall but I decided it was my first choice.

"I'm getting this one." I said pulling it from the wall turning it over reading the back.

"Not a bad choice! Simple, elegant and discrete. Let me grab a basket since we are picking things." She said walking off to the front of the store coming back with a basket with something already in it.

"What did you find?"

"Oh, I figured this little thing here would be useful to have for your adventures." She replied pulling out a much larger dick that she strung through a harness.

"See you wear it when you are with your special lady." She teased draping it across her jeans pretending to thrust.

I laughed at her obscene gesture and waved her off. In retrospect I wish I had responded better while in that moment I had not discovered sex with women but Dee recently ventured down that path and my response made her less than enthused to tell me about it. I know it seems lopsided that I tell her just about everything when it comes to my sex life and she hid things but years later I would learn my adventurous spirit intimidated my mostly vanilla friend.

I went back to scanning the wall noticing the anal toys wondering if it was something I would be into while she went and put the strap on back. I was a bit embarrassed when she walked up behind me.

"Oh I didn't know you were into butt stuff."

"Oh I mean I haven't tried anything but I dunno." I stammered.

"Its cool, not my favorite but I have tried it a few times. Just make sure you use lots of lube, go slow and find a guy smaller than James." She laughed digging back in the basket for the things she picked up along the way.

My eyes went wide thinking of even attempting to take him back there. He never showed any interest in doing anything like that and I was far from ready from bringing it up but it was another thought I would file away for later.

"Ok so you get to pick which one of these you get as my first gift to you. This one is a set of nipple clamps and this one is nipple suction. I don't know if clamps will good hurt but I'm sure they will hurt at least a little, suction seems more your speed." She beamed holding both boxed in front of her.

I am not sure why in that moment I saw it but she knew me better than I pretended to acknowledge. It was a weird thing to have an emotional response too but I felt love for my friend in that moment and question one was answered probably along with the rest. I wasn't sexually attracted to her I loved her and the rest was just me being nasty.

"Ill take suction and good first pick, maybe this wont be so bad." I smiled looking over the box actually quite excited to try them out. I dropped the box in the basket and proceeded to look at the display to our right that had "massagers" you could turn on and play with.

As per her new habit my companion disappeared to another part of the store no doubt searching for my next purchase. I turned on the toy in my hand and good lord was it strong, I put it down immediately knowing that it would probably kill me if it came into contact with anything between my legs. In my hurry to put it down I didn't actually turn it off so it vibrated like crazy on the display shaking a few things off their display stands. I frantically started trying to catch the run away toy along with putting things back while it buzzed so loud I felt the stores next door would see my shameful juggling. After replacing everything I looked around to see the woman at the front counter simply smiling and Dee laughing her ass off walking up to me.