Heads or Tails

This is a post I wrote several years ago but never posted because the other girl involved did not feel comfortable with it, in fear that someone would guess who it was. I figure enough time has passed (and I don’t really have anyone reading this that knows her) and I really don’t have anything new to write about as of yet. I just noticed that I wrote the actual playing post three years ago yesterday. I found the Crazy, and ironically, that post is called Crazy. I hope you enjoy!

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She said she wanted to flip a coin. Heads she would tell me something, tails she wouldn’t say anything. I thought she was kidding, but apparently she wasn’t. When she came over that night for our weekly sleepover, she flipped a coin. It was heads.

She started to say something, but stopped herself. I tried as hard as I could to get her to tell me what she wanted to say. She said it seemed creepy. I told her nothing could surprise me, and she should know how open minded I am. She told me then that at the last sleepover she had urges.

I asked what kind of urges, and she said she had the urge to kiss me. I told her she could if she wanted. She said she didn’t feel right, that the urge she had made no sense, that it didn’t seem right. I asked her what seemed so wrong about it. She said it just seemed wrong because I was a girl, her best friend, and that she didn’t know where these feelings were coming from. She was afraid that it would change our friendship, hurt it. She was afraid it would become an expected thing.

I told her that everything she was feeling was completely natural. I explained that since we know each other so well, trust each other with anything, it could work. It would be an experiment, and that I was game for anything she wanted to try. I asked what she pictured us doing, how she would want it to play out, what she was curious about.

She described that she saw us kissing, making out, and groping each other’s nipples. I kept calm, but inside I began to burn with lust. Even with the simple way she described what she has been imagining, I was hot. I wanted it too, and what I saw sounded very sexy.

She then told me that her biggest problem with the idea of being with a girl was that when
she got really turned on, she likes a penis inside her. I suggested she could use strap-ons. She said she had already considered that.

She was still very hesitant, and so I explained to her how my experience was when I began to experiment with Sarah that first time. I also told her that I would not push her, and everything was up to her, and she would have to make the first move unless she said otherwise. She told me that in a way that was good because she was too chicken.

I pressed a little more, and asked how she would react if I helped her out by making the first move. She said she still was trying to get comfortable with the idea, but was still thinking about it. I told her that was fine, and to take her time, to just think about things.

The next day she texted me, told me she was getting comfortable with the idea of us experimenting. She seemed to ease up a bit more when I said it was just an experiment for her, and for her to take her time. I got a text the next day again, saying she was looking at strap-ons, and asked if I had ever thought about using one.

I told her that strap on usage had always been a fantasy of mine, but they were always so expensive, I never took any steps to make my fantasy a reality. That is when she said she could buy a cheap one for us, or we could go half and half on one.

All day, I had the image of her using the strap-on on me, and all day I considered my
options. That night, I went online and did some shopping of my own, reading reviews of different dildos and harnesses. I decided that the Jaguar harness and the Raquel dildo would be the best way to go. I went ahead and ordered them at a discount in exchange for doing a review. I can’t wait to try them out when they get here.

Faked

I got back to Leah’s apartment, where her and The T were waiting. I cuddled with The T a bit, before heading into the bathroom to change into my sexy clothes. I wore my yellow negligee with a black thong. They both told me how sexy I looked. The T and I made out for a bit, then we went to Leah’s room. Leah stayed in the living room to finish watching her show.

Things were a little awkward at first, so we started slow by just kissing with some heavy petting. Once I felt comfortable, The T and I got naked. I had never put on a condom before, so he had me do it. I fumbled a bit, but finally I got it.

I wasn’t really wet enough, so he decided to go down on me. It felt good, but not quite good enough. Luckily though, that made me wet enough. He slid his cock in slowly, riding on top of me. We kept this position for a bit, until he wanted to fuck me doggy style.

I had a problem keeping my ass higher than my head, but eventually we had the right position. We decided to get the bullet out, to try and make me cum. That is when Leah came in to join us. Before I got the bullet onto my now dripping wet pussy, she asked to go down on me. I said sure, and opened my legs once more.

Unfortunately, she did not last long down there because all she could taste was condom lube. I did not blame her one bit, so I went down on her instead. She was the first girl I went down on, and I hope she won’t be the last. I did just as I had always imagined myself doing with a girl, and slowly traced my tongue all along the pussy lips, then around the clit. She moaned, telling me I was doing it just right, but it would not make her cum. She had me stop so that The T and I could continue and she could use her vibrator.

The T had me put on a fresh condom and told me to climb on top. It was my first time on top, so the positioning was very awkward at first. Eventually I had a good hythm going, where I gripped the top of the head board and he used his hips to move me up and down. Sadly, just when I was really enjoying that position, I got a bad cramp in my hip, so we switched to him on top.

This time I had my bullet ready, and I got it on my clit while he fucked me. Leah stopped what she was doing with her vibe to encourage me to cum.

“Oh God, Leah, shes so close, shes so tight,” The T moaned.

“Ooo, I can tell shes close, by her breathing,” Leah said.

The truth was, I was close, but not close enough. The pressure of needing to cum was building, physically and emotionally. Unfortunately, the emotional pressure to cum outweighed the physical. Leah was so excited that I was gonna cum, I could not disappoint her. I started making the sounds I make when orgasming, and flexing my pussy around The T’s cock. They both encouraged me while I was cumming, and talking dirty to me. After a few seconds, I slowed down on the moaning and relaxed.
After I “came,” Leah went back to the living room to watch another show of hers. Once she was out of hearing distance, The T asked the dreaded question.

“You didn’t really finish, did you?”

I decided to be honest. “No, she was pressuring me so much I just couldn’t. I lost the closeness I had to cumming,” I said to him quietly.

“I understand completely, and thank you for being honest,” he said back.

That was the only time I faked my orgasm. I never really saw the point in faking. I think that if you fake an orgasm with someone, they think they are doing something right, and will never really know how to get you off. The only reason I faked this time was to not disappoint my hostess, who I knew we would never be hooking up again. I was glad The T was so understanding.

We ended up putting on a fresh condom so that he could at least have his orgasm. Leah was right, it was good sex with him. It was easy to turn down Toby after fucking The T. The T and I never got together again, unfortunately, because Leah decided she did not want to share him anymore. She was apparently jealous to see me fucking her “best friend.”

Crazy

It started with her rolling over and grabbing my waist. She then leans over me, and without  hesitations she buries her face nice my neck. She bites and nibbles all over, She starts scratching her finger nails all over my back and neck. It only lasts about three seconds, and she rolls back over to her side of the bed. I tried to stay very still, hesitant to move, afraid to break the moment. She asked if I was ok. I told her that aside from being very turned on, I was good.

A few minutes later she starts to rub my back. Slowly I relax, but still afraid to move. She has no idea what she is doing to me. The back rub lasts about five seconds, and she asks how that was. I said it was good.

We begin to calm down, or at least she does, whereas I was trying to absorb every bit  of self control I had, afraid to scare her away.

She surprises me by asking if she can fuck me with my strap on. I told her of course, that was why I got it. Carefully and quietly I get out of bed to get my newest toys. I hand her the strap on and dildo. I grab my lube and ask her how it works, whether I should put it on/in me, on the dildo, or both. She said both. When the harness was on, I handed her the lube for her to put on.

Unsure at how squeaky my bed was, I shifted to the middle, and she positioned herself above me. She asked if I was ready, and I told her to put it in. We both guided the silicone cock into my now dripping wet pussy. It’s cold, but it feels so damn good. She gets a good, slow, steady rhythm going. It lasts about ten seconds before we notice the loud squeak of my bed.

“Damn, I really want to fuck you,” she tells me.

“I know. I want you to too, but we can’t wake my mom with the squeak of the bed.” I remind her.

“What about the floor?” she asks.

“We could try. I could put a towel down on the floor and it could work,” I answered, eager for her to fuck me.

“Maybe next time. I am kind of tired. We should sleep now,” She answered.

“Really? You expect me to sleep like this?” I ask.

She says yes, then rolls over and goes to sleep, as I lay there wishing I could get off, yet knowing that would probably freak her out. I just have to wait until the next night, when I am alone.

All About Her

She’s spontaneous. She’s unpredictable. She’s wild and crazy in bed. With her I never know what’s coming next, or how long it will last. One second she will tell me no, then when I least expect it she has her way with me. I am at her disposal. She can do whatever she wants.

She bites me. She scratches me. She teases me. She drives me nuts. I love the rush she gives me. I love not knowing what is coming next, and her surprising me with her impulsiveness. I think she will do one thing, instead she will do something else.

I want to reach out, to touch her too, but this experiment is all about her, and her using me to satisfy her curiosity. I don’t know what she is comfortable with, so I keep my hands to myself, only rarely mirroring what she does to me when she asks me to.

She knows what she does to me, and she uses it to her advantage. I swear, she will be the death of me.

Yeah

I picture her on top. Riding me like a cowgirl. This time it’s my turn to wear the strap on. She talks dirty to me, telling me she loves my cock, tells me to fuck her hard.

I thrust my hips up and down, watching her tits bounce up and down.

“You like that?” I ask her.

“Yeah. Harder. Harder. Push it. Oooh, yeah,” she moans.

“Yeah?” I question.

“Yeah,” she responds, unable to say more as the orgasm takes control.

Hot

I heard from her boyfriend she likes wild sex. I heard from her she likes it rough. I never pictured us doing anything, just because she never showed any interest in women. That is, until the day she told me had urges.

After a few days talking back and forth, we decided to try a strap on.

Now, whenever I picture it, it’s hot; her fucking me, on top of me. Biting and kissing my neck, me grabbing and scratching her back; lifting my hips up and down, taking in more of her.

I think of this image when I masturbate now. I think her name over and over, closing my eyes tight to hold onto the image of her biting, kissing, and fucking me. I think of her as I cum, calling out her name in an orgasmic moan.

Strap On

A week or two ago my friend Maya approached me with the idea of her and I experimenting together., She said she was unsure how far she wanted to go, but so far kissing and groping (above the waist), seemed ok. She seemed concerned on why she was having these feelings, and I tried to explain as much as I could, detailing how I first started out.

Her biggest problem seemed to be that I didn’t have a penis, and a penis is what she craves to have filling her pussy when she is turned on. I suggested strap on usage, and she said it sounded like a good idea. We both did a little shopping online, and I ended up getting the Raquel dildo (silicone) and the Jaguar harness (leather).

I waited anxiously all week, and today they finally came. Tonight I will test out the dildo by myself, see how it fits me. Eventually, she plans to wear the strap on and fuck me with it. I can’t wait.

It took me a while to figure out how in the heck the strap on fit or came on, but eventually I was wearing it and the dildo. For some reason I really liked wearing it, especially sitting at my desk, playing at the computer. Wearing the harness and dildo made me really horny, and I plan to go fix that problem as much as I can as soon as my batteries are done charging.