Chasing Me Chasing You

An uncollared submissive struggling through depression, motherhood, and the constant craving of her next orgasm.

It Always Works Out in the End

The package had arrived two days ago but I was instructed not to open it until I had time to complete the task. So there it sat, tempting me until today when I finally found sufficient time alone to open it, examine the contents and follow the instructions that he had included in the package. I knew roughly what to expect but not the specifics of the challenge.

You see, he’s finally arranged to come and visit me. We’ve been talking for a couple of years now but we just haven’t ever found the time to be together in the same place. We have missed each other by a few hundred miles or a couple of hours on a few occasions which has been frustrating to say the least. He will be finally arriving in a little over two weeks and be staying for around three days. I can’t wait, we have so much to catch up on and so much sex to have to make up for the times we haven’t been together.

Over the years we’ve exchanged a lot intimate thoughts and fantasies, the occasional video, stories and even collaborated on writing erotica. I know that he has one unfilled sexual desire and that is to have anal sex. Not judging, but his partner has steadfastly refused to even consider trying it which has caused him a lot of angst and frustration over the years I have known him. My recent attempts at anal sex have been less than stellar as well due to my lack of preparation, a fact he is aware of so I have a fair idea what the focus of the task will be and what the likely  contents of the package.

Opening the box I find an envelope which I assume contains the instructions, a tube of Wet Platinum Premium Lube, a small anal vibrator, a medium size butt plug and a longish rectangular box. I’m very curious about what’s in the box so I open it up to find a very life like silicon dildo which can have a vibrator inserted into the base if desired. The resemblance to a real cock is amazing. Even the colur is close to pale pink skin. There is also a suction mount that I assume helps secure the dildo to a wall or floor.

So now I have the contents spread out on the bed I decide it’s time to open the envelope and see what he wants me to do with all of this. Tearing open the envelope I find a couple of A4 pages of typed instruction.

The first instruction is that he wants me to video the session and send him a copy once I’m done. He has been specific around the camera angle he wants so that he can see my ass being penetrated close up. He insists that I do a short test video to make sure the positioning is as he has asked.

It turns out that the life like cock dildo is in fact ‘a clone a willy’ silicon replica of his cock. He says that once I’m comfortable taking his cock up my ass he will know that we are both ready for the real thing. How amazing is that. Only he would have been that thoughtful.

The rest of the instructions are more about ensuring I’m clean and that I warm up properly so that I have the best chance of taking his cock in my ass first time. Looking at his cock I think that this will be doable. He has often said that he has the perfect cock for anal sex, long and thin. I think the girth his  fine, but I’ve seen some that are bigger. I think I’m in agreement to his assessment. Time will tell.

Okay, I’ve got myself prepared. A little clean out and lots of lube liberally applied. Test video done.

Now let’s get into position and get on with taking his cock in my ass.. He wants me positioned on my knees so that I can place my ass back onto the cock and allow me to rock back and forth.

I am finally start the recording and get on with it. I’m already wet with anticipation. Maybe I’ll get him to fuck my pussy after the anal preparation. He never said I couldn’t.

Using my fingers first. I reach back and rub my finger around my anus and slowly slip the tip of my finger inside my ass. Moving in in and out I slowly increase the depth of penetration. Once I’m feeling aroused and relaxed I next add a second, then a third finger. I’m may have also missed my ass a few times and ended up fingering my pussy. Oops.

After a few minutes I feel I’m ready to use the butt plug to further open up my ass. His instructions said that I have  to continue with inserting and removing the plug until my ass gapes and remains open for two seconds before closing. Following his instructions I slowly insert the plug. I know from a previous video exchange that he loves seeing the plug slowly disappearing up my ass. So to give him some added viewing pleasure I make sure I do this a few times. I also push back trying to expel the plug creating a bulge which looks amazing and hot. After about five minutes the plug has done its job and my ass is staying open. I do enjoy sticking my fingers into my open ass. Such an anal slut.

I’m ready for the last part of the task. Taking his cock I secure it to the floor using the suction cup he supplied. Next I grab the lube and apply a liberal amount to his cock  and slowly jack the cock smearing the lube over its length. Another squirt and I lube up my ass. Ok, so here goes. Squatting down as directed I slowly lower my ass towards the tip of his cock. I feel it start to push against my anal opening. With a bit more pressure I feel the head slip past my sphincter and into my ass. Pausing to get used to the cock in my ass, I take a few deep breathes. I pull back off his cock and slowly impale myself on his cock again. This time a little deeper. The next time I pull his cock out I leave the head inside. The next down stroke takes him deeper into my ass. It’s a little uncomfortable but I think I can do this.

Moving slowly and deliberately I take my time getting used to his cock in my ass. As my excitement increases, so does the speed of my movements,  lowering myself further onto his cock. With one last push I manage to bury his cock balls deep in my ass. There is some slight pain and some uncomfortable twinges, but it’s not too bad. I’ll do better next time, and the time after that. I then raise myself up and off his cock and turn off the video. That completes his challenge for the day. Now I’ve just got to clean up and send him the video for him to review my progress. I hope he is pleased.

I love that he sent me his cock to practice on. I know that when he gets here I’ll be ready. Hmmm, maybe I need to practice my deep throating skills as well.

Attainable Goals

As I sit here and drink my second cup of coffee for the day I keep coming back to what I want to accomplish this year. As my husband sits on his computer learning Swedish, apparently, I feel the need to also improve myself. I’m not good at languages (as my fruitless six years of Spanish will attest). There are quite a few other goals that I would like to work on though. Finishing a quilt or two that have been started and had to be set aside. Losing weight is always a go to goal. I’m still down on what I weighted this time last year, but another thirty pounds wouldn’t hurt.

However, I have another goal for 2017: anal training. Prior to Jack’s last visit we had discussed how much fun it would be for him to take my ass. We didn’t really have time when I visited in October, so we were both looking forward to it. I thought I had prepped okay. All anal November was a bit of a wash, but I wore my Njoy a bit and tried to stretch when I thought about it.

Apparently thinking about it wasn’t enough. When we did get a chance, in our hotel room, during his visit in December, things did not go well. Although I was able to eventually relax with the help of the Doxy, it wasn’t long before I had to stop. The Njoy did not prepare me for his girth or length. And while I’m sure he would take that as a compliment (in fact I’m pretty sure he did), it crushed me. After all the talk and hype about anal over the last few months, to be thwarted again, was a real blow. Especially as I was mostly my own fault for not preparing better.

I am hoping to see Jack several times this year. It depends on finances and schedules, but my fingers are crossed. In any case I don’t want to be what holds us back from anal sex next time. So I am going to try and start a regimen. I’m sure my husband won’t mind helping me stretch occasionally too. It’s good to have motivation to reach your goals.

Check out how everyone else is starting off 2017 by clicking below.

Wicked Wednesday for post Stockpiled Cravings

November Goals

The last few days have been pretty rough. I wasn’t in a great place on Sunday and things went down hill through the afternoon. Sunday night I was a crying mess. I think my poor twitter boyfriend and Jack were both ready to strangle me through the internet. I just couldn’t pull myself out of it.

In the end Sir and I had a good talk. It was long and emotional, something which usually causes us to avoid it at all costs. But we have been drifting too long; we needed this to figure out how to come back together. Work stress and various other things have been pushing on each of us the last few weeks, and it finally came to a head. In the end we were both feeling a lot of the same loneliness and overwhelmed confusion. And, as usually happens, we realized our silliness and had some amazing make-up sex.

So…on a completely different note, I have decided to take part in two ‘events’ going on in the month of November. The first (tangentially related) is All Anal November. It’s one my 101 Things goals and something I’ve always wanted to try. We are setting some rules that oral is still allowed (because Sir still wants to be able to demand his cock be sucked). Basically I’m not allowed any vaginal penetration. No dildos, nothing. My pussy is already twitching in desperation. But, Sir wanted to look at enemas as a regular thing, so this will give us the chance to try that. Who am I kidding, I’ll be whining about how much I want fucked within a week.

The other thing I’m attempting this year is NaNoWriMo, which stands for National Novel Writing Month. The goal is to write 50,000 words, or a rough draft of a novel in the month of November. I have an idea and a chapter outline, we’ll see if that’s enough. I’m supposed to aim for around 1,700 words a day to stay on target. With trying to write sexy things on here and write that, it should be an interesting month.

A lot of things to look forward to and to keep me on track for the next few weeks. Weight-loss, writing, and lots of anal sex. This might be my favorite month this year.

Yeah, Butt

I bought Rye three things for her trip to California. First, I bought her a brand-new lube shooter. it’s a kind of syringe with a modified tip for shooting lube into an asshole (or vagina). If you’ve never taken the opportunity to fuck an asshole which has been FILLED with lube beforehand, I encourage you to give it a go!

Second, I bought her a six pack of disposal fleet-enemas. Those may or may not go with her on the plane. It will depend on whether I can learn how well they handle depressurization in the luggage compartment of a commercial airliner.

Lastly, I bought her a “standard” enema kit.

For someone like Rye, who is enthusiastic about anal and gets the good kind of woozy when she’s sexually humiliated, you might assume that being “enemaed” (or told to enema herself) is not a big deal. You’d be wrong. This step toward enema play is a big deal.

This is the first time that I have ever pursued an area of play without first discussing it with her. Her ass has always been in-bounds. I have, on occasion, fucked her asshole without so much more warning than squirting lube on her asshole in silence. She has always taken whatever I have thrown at her. But I don’t throw all that much at her, really. I don’t surprise her with kink. It isn’t really feasible in our lives as parents and it isn’t necessarily part of who I have been as a dominant.

Honestly, this kind of asymmetrical play is not really my thing, normally. I usually make sure that whatever we are doing has a chance to please both of us. This is mostly a technique by which I manage the possibility of failure. Enema play will be something completely different for us. This will be an unknown for both of us. So, it is very different that I have come to Rye, tools in hand, and told her that she is going to receive an enema. This is the first time when I’ve presented her with something that is totally for my benefit and offering fuck-all in exchange. Taking completely without giving, at all.

In a way, it feels a bit like I am forcing this to happen against the natural grain of our relationship. It is the sort of thing that would fit better into a Master/slave or Owner/property dynamic than the more playful rhythm which we have been enjoying. I recognize the poor fit at the same time that I am compelled to ignore it. Perhaps the fact that it doesn’t fit is why I want to do it. For the first time, I’m not going to think about it too much. I’m just going to make it happen.

As I alluded before, I told myself that the reason I bought these things was because I wanted to give them to Rye for her trip to California. The man she is going to see has said, in no uncertain terms, that he is going to take liberal use of her asshole. I welcome this! But, if I am going to loan my wife to someone for butt sex, I am going to at least make an attempt to make sure that it is safe, clean, and awesome.

I want the experience for everyone to be as perfect and memorable (in a good way) as possible. In part, that means I want her to fuck like a pornstar. I know she can handle the acts well enough on her own. But, we all know that porn stars enema before doing anal porn shoots. It makes everything clean, easing post-orgasm body anxiety.

But, honestly, it’s for me. All of it. The novelty, her discomfort, her cleanliness and the easy sluttiness I want it to inspire. All of it is in the service of my desires.

Something to Njoy

Lately Sir has really been back on an anal sex kick. It generally comes in waves; not that I’m complaining. If my stomach has a rough day or two, or we’re busy, anal often gets halted. And after a break, for whatever reason, I find that fall ‘out of shape’ quickly.

So, Sir has decided that this is no longer acceptable. It wasn’t all my fault, but it’s obviously something that needed addressed. So the other day I got an early birthday present.

Rye's new Njoy butt plug.It’s not quite as large as my glass plug, but he didn’t want me to start out with the Njoy 2.0 just yet. And what shocked me was how much easier it is to put it and wear. I guess I was sort of under the impression that all butt plugs were created equal. No, no, no. This is not the case, my friend. And, after the easy time I had putting in it, I could wear it for hours with no pain. This included three hours on Sunday during the toddler party. Enough pressure that I’m not going to forget I’m wearing it, but not so much that I can’t focus.

I know Sir is looking to move to more of a 24/7 set-up with the Njoy. I’ll be allowed to take it out for anal sex, obviously, and for bathroom reasons. Other than that, I have a feeling he’ll want it in. I’ll admit the idea of sleeping in it has me be a bit nervous. I’m not sure why. The first time I wear it to work should also be interesting. I’m sure he’ll let me take it out if I get too nervous and/or upset at the office. For awhile. But a time will come (knowing him sooner rather than later) where he just says, ‘suck it up, buttercup’.

For now I will continue my practice and hope that security at work doesn’t turn up the sensitivity one day without warning.

 

The Gift of a Key

This is the next installment to the Beth and Graham story. If you want to catch up you can link to Part IPart II, or Part III here.

~

“That was excellent salmon Graham, thanks for your help with dinner.” I cleared the plates quickly and returned to the table. Graham and I had relaxed most of the afternoon and enjoyed our trip to the store. His recipe was amazing and I know Sir was impressed. Sir had been working since his shower, so I was hoping he was going to take the evening off. I was surprised when he started to walk down the hall again to his office, until he called for Graham to follow him. I walked down the hallway behind them, not wanting to miss an instruction from Sir.

“Cunt, come kneel next to the desk. I need to talk to Graham for a moment.” I moved quickly as Sir gestured to Graham to have a set across the desk. In his office chair he seemed even larger and more in command than normal. Kneeling at his side I’m sure to Graham he looked like a king with his sex slave looking down on a lowly serf.

“How have you enjoyed your visit so far?”

“Yes, Sir. It has been lovely. Thank you for allowing me to visit.”

“I know you and Beth have been close on Twitter for along time. Does our D/s reality still appeal to you?”

“It does appeal to me greatly. But my wife doesn’t feel the same. And although she gave me permission to visit a friend and experience a scene with male dominant, I don’t think she would ever be comfortable with me having a regular female top. But I love her more than I need this, so our BDSM dynamic will have to be limited it to what she is comfortable with.”

“So you seem to have resigned yourself.”

“I wouldn’t say resigned. I certainly hope to have more experiences like this. I’m so grateful to her. I wouldn’t have felt right coming here at all without her blessing.”

“Good. You did well this morning, but I wanted to make you were comfortable being here before I gave you this.” Sir handed Graham an envelope. He pulled out a short printed letter. After he read it, he and Sir kept talking, but he handed it to me to read while they spoke.

~

Sir, Please give this to Graham should you deem it appropriate.

Graham,

This letter is to clarify to you that I trust you. And after several conversations with Beth’s Sir I trust him too. You have my permission to enjoy this weekend. You’re not cheating. You’re not being unfaithful to me. This is an experience I don’t know that you will get a chance to repeat. And Sir assures me that he will make sure you earn everything that he decides to give you.

Please remember that I love you. Your service to me will be through Sir. I expect you to make the most of this visit. See you soon.

Hannah

~

Short and to the point, but knowing Graham, it was necessary for him. I was surprised he had done so well with everything that had happen over the last few days. I knew that some of our activities would eat at him if he didn’t have those clearly expressed words of permission.

But Graham didn’t know about the letter that had arrived a few days before he arrived from Hannah written for Sir. I hadn’t read it. Sir didn’t offer and I didn’t ask. I was obvious that Hannah was putting a lot of trust in Sir. And that I would have to trust that the two of them knew what was best for Graham. This was part of that.

Sir took the letter from me, folded it, and placed it on his desk. Then he reached into this top drawer and removed something small. Putting it in his pocket, he told both of us to go to the play room and prepare. I moved quickly so as to explain that prepare meant we were to get undressed.

When he entered a few second behind us he told Graham to stand next to the St. Andrews cross. Sir pulled some of our larger rope out of a bottom drawer and began to tie him to the cross. I watched almost mesmerized. Sir would rub Grahams chest and legs as he tightened each knot. There was a sexual energy in this exchange, but Sir’s demeanor never changed. Graham had his eyes clothes and was already moaning.

I knew he was hoping to have experiences like this. Hannah wouldn’t permit him to go to clubs or purchase their own equipment, so I was sure this was his first time being tied to anything. Normally Sir would put cuffs on my wrists and ankles before clipping me to the wall, but as I thought about it I realized that my cuffs were probably too small for Grahams limbs. The larger rope would have to do.

When Sir had Graham secured to the cross he walked over to the toy box and pulled out a riding crop and one of the smaller canes. Grahams eyes followed the cane as Sir walked across the room toward me.

“Pick one.”

This was a pretty standard practice for Sir. He would have me pick an implement that he would use on me. But now, I wasn’t sure if I was choosing for myself or Graham. I went with the cane, hoping it was the former. I was wrong.

“Here you go, Beth. Show me your form.” He handed me the cane, but I just stood there staring at it. Sir lightly slapped my right cheek.

“Let’s go cunt, before I get impatient.”

“Yes, Sir. Sorry Sir.”

“Graham you will count. And Beth, no holding back. If I think you are being too easy on him I will take over. Make him earn his reward.”

Walking over to Graham I stared as his cock was already straining against the cage. I ran the cane up both of his legs. He moaned. I tapped the end on his already hard nipples. He turned his head away from me. I tried to channel Sir.

“Look at me.” Graham instantly opened his eyes and turned to me. I don’t think he was expecting me to talk. I’m not even sure what possessed me to, but I didn’t hear a correction from Sir, so I kept going. As I walked in front of Graham his eyes now followed me. I wouldn’t have the element of surprise, but I didn’t want it. I wanted him to know the strike was coming, because it was going to hurt.

The cane made a slapping noise as it hit his upper thigh and a thud followed as his body jerked against the St. Andrew’s cross. He teeth were gritted together as he groaned and a red line almost immediately appeared.

When I was on the cross, I always wanted the hits to come closer together, as it was easier for me to get into subspace. So I decided to stick with that method with Graham. My blows were deliberate and in quick succession. Up and down his thighs and torso. I hit his nipple once and he yelped with such a pain that I couldn’t bring myself to do it again. I have no idea how long it took me to get to fifty, but by the time I did I could feel his exhaustion. Luckily Sir told me to stop.

“I am impressed. With both of you. Good form Beth. And Graham, I’m deeply impressed with you. You handled everything she threw at you.”

“Thank you Sir.” Graham was breathing heavy, but his eyes were focused.

“Now, let’s see how you handle your reward.”

It almost sounded more ominous that the beating. Sir reach into his pocket and pulled out a small key. I looked at it with confusion, but Graham’s eyes had gotten very wide.

“This, dear Beth, is a copy of Graham’s cage key. His mistress sent to me in a letter a few days before he arrived. In that letter were specific instructions of when and if I was meant to use it. She has agreed that certain experiences would be beneficial to you and she wants those to happen in a protected setting. Therefore, Beth, take this key, and remove Graham’s chastity device.”

I smiled as I took the key. Graham still looked confused, almost scared. I unlocked the cage and carefully removed it; setting it on the floor next to the cross.

“Now, Beth, Graham has heard of your talents from afar for a very long time. Let’s show him that I don’t over exaggerate your skill.”

I looked up and Graham and smiled as I watched his cock timidly grow. Unsure how to act without the cage surrounding it, his erection almost seemed unsure how to respond. I was practically giggling when I began licking and tonguing his shaft. He began to moan and strain against the ropes almost immediately.

Oral sex was always something that he had fantasized about. We had talked about it at length. When I had originally talked to Sir about Graham visiting, it had been a desire of mine to service him in this way. When the cage restriction had been announced I was upset that this wouldn’t come to fruition. Now I was enjoying every minute.

He filled my throat as I took him deep. I rubbed the cane marks on his thighs with my fingers and nails. He hissed and moaned. Unable to distinguish the pleasure from the pain he thrust into me one second and pressed back against the cross the next. Soon, his body took over and he was thrusting in earnest. I opened my jaw and stuck out my tongue to massage his balls with each thrust. His moans increased and then stopped as he came. I had meant to have him come all over my breasts (another fantasy of his), but the connection I felt as I drank in all of his orgasm was too amazing.

I sat back on my heels to await further instruction. As I looked up at Graham’s face. He was leaning back against the cross, breathing heavily, but a huge grin had appeared.

Sir handed us both bottles of water and tugged a strand of my hair affectionately as he walked by. He didn’t mind sharing me as long as he got to show me off. I am pretty sure we both loved that, actually.

Graham set the bottle of water down on the floor and gave me a quick smile before looking at Sir for further instruction.

“Beth, do you want to be my little piggy?”

“Yes, Sir.” I nodded eagerly.

“Then come assume the position. Graham, grab three lengths of rope from that second drawer and bring them here.” Graham began following the order, but I could tell he wasn’t sure what was happening. I kept waiting for him to meet my gaze so I could let him know it was a good thing, but he stayed focused on his task.

I climbed onto the spanking bench as ordered. Placing my hands together under the bar I rested my knees on each of the side bars. I let all my muscles relax as I sank into the padding. Taking one of the pieces of rope, Sir began tying my hands together. Without words he indicated to Graham to use the other two lengths on my thighs. Once they finished, Sir checked to make sure they were secure.

“Pick a toy Graham. Any toy you like. And use it on our little piggy until I say otherwise.”

Sir walked around to the front of the bench and unzipped his pants. Without order I took him into my mouth. I couldn’t see Graham walking about the room, so I focused on Sir’s cock until I felt him standing behind me.

I’m not sure what I was expecting; some impact toy, I guess. What I wasn’t expecting was the sharp point of the wartenberg wheel pressing into my flesh. I wriggled on the bench, but my legs were tied fast. Plus, Graham’s sadistic side emerged as he began to push down and drag the wheel whenever I attempted to move away. I was trying to focus on Sir’s cock, to let the pain take me into subspace. However, soon I felt Graham’s erection against my thigh. And I wasn’t the only one who noticed.

“Seems you are finally ready to help me roast our little piggy Graham. Put the wheel away and grab some lube off the shelf. Get yourself good and wet, and when I say, you are going to take her ass.”

“Yes, Sir.” He wasn’t even attempting to hide the eagerness in his voice.

My ass and pussy were soon dripping with a mixture of my own desire and the water soluble lube. I tried to indicate to Sir that I was ready by taking him as deep as I could. I’m pretty sure he understood my message, but liked it too much to act upon it until he wanted to. He never was one to bend to another person’s schedule. Graham rubbed the tip of his cock against my thighs. He was just as eager as I was.

“Okay, now.” As he gave Graham the order he grabbed the sides of my head and began to face fuck me slowly. I moaned around his cock. Graham pressed against me for only an instant before sliding in.

It only took a few thrusts for them to synchronize their movements. I relaxed every muscle and just enjoyed each moment of the glorious double penetration. Everything slid in and out and filled me just like I had dreamed. Being used by two men had topped my bucket list for a long time, and the chance to experience with these two made it even better.

It didn’t take long before we were all a moaning, coming mess. I don’t remember much after I was untied. The blissfulness of being used and getting to please two men I cared so deeply for had me drifting off to sleep. Sir carried me to bed.

I woke up around 11:30 to find myself sleeping alone. I ventured out into hall and down to living room. As I rounded the corner I heard laughter. Sir and Graham were sitting in the arm chairs on the opposite wall. Each had a whiskey tumbler and similar belly laughs. I only heard part of the discussion; something about each growing up in religious households.

I smiled at the thought myself and tiptoed back to bed. Graham would have to leave tomorrow and his cage was probably already back on. I crawled back in bed thinking of the big breakfast I would make for them. I hoped this visit was everything he had hoped for. It was more than I could have dreamed. And I still occasionally dream about it. On really good nights.

Creating a New Way

“It’s not going to fit.” I wish I had been joking. Just fluffing his ego or something; but I wasn’t. “There’s not way; I’m sorry.”

“Oh, it will fit, maybe not today. But by the time I get back down for a visit, mark my words. I’ll fit.”

*                      *                           *                       *

That was two weeks ago. Two days after he left I got a package from a lovely sex shop in London he had taken me to once or twice before. In it were three progressively larger butt plugs. Each was a plain, stainless steel tear drop shape. The smallest had a red ‘X’ on the end of the stopper, the next a black ‘X’, and the largest has a pretty emerald colored jewel. There was a note with them:

X = 3 days, at least 2 total hours/day

X = 4 days, at least 2 total hours/day

Gemstone = 7 days, at least 2 total hours/day, work up to 1 hour blocks of time

See you in two weeks cunt. xoxo

The first day was rough. Even the smallest plug was larger than any I currently owned. I found if I came once, and put my clit vibrator to high, I could relax enough to get it in. I tried to wear it as long as I could, but I ended up with several short spurts to equal my two hours.

The next few days weren’t so bad. Even moving up to the black ‘X’ size wasn’t as difficult as I had feared. Sir texted and told me to take a picture. He has colored the ends so he could tell which one I was wearing; I had wondered why they all didn’t look the same. He was happy with my progress, but warned me that the last size jump would be hard. His vote of confidence that I would be good to go when he saw me was not longer reassuring.

The day I first put the largest plug in I cried. And considering that I didn’t cry when I broke three fingers slamming my hand in the car door, that’s saying something. Even post-orgasm with the vibrator on it’s highest setting, it took me nearly ten minutes to put it in. I only wore it for another ten. There was blood. I called Sir bawling.

“I told you this was going to be difficult, but I wouldn’t ask you to do anything you weren’t capable of. Relax and give yourself an hour or so and try again.”

“Yes, Sir.”

“That’s what I like to hear.”

An hour and a half later it still hurt, a lot. But after getting it in place I was able to leave it for an hour. My body adjusted quickly after the initial pain.

The next few days didn’t help as I continued to struggled, but once in I could leave it with little pain as I went about my chores and regular work. I could feel it, but only insertion and removal were painful. My anxiety grew, however, as it was not his intention to very slowly put his cock in me and then stay perfectly still. I was worried how anything rough or even just regular movement would feel. The last thing I wanted was to safeword after all the work I had done.

*                          *                          *                           *

I wore the plug as he arrived on Friday evening. I had dinner prepared and his drink waiting for him. He had me bend over and present myself to him before we ate.

“I am happy you are wearing the plug to dinner, cunt. I appreciate your commitment to my pleasure.”

He snapped his fingers and I sat down on the floor next to him. All that I laid out for myself was a napkin. Tonight he decided to feed me rather than give me a plate. It was a welcome gesture as I’m sure he could feel my nervousness.

He decided to wait on dessert, so I put the cheesecake in the fridge and we went upstairs. He told me to remove the plug. When I reentered the bedroom his dress shirt and tie were on the chaise and he was throwing his socks in my hamper. I would wash them in the morning.

He pulled the large bottle of lube from the drawer in my bedside table. I was ordered to grab a vibrator and get into position on the bed. With a mixture of excitement and dread I just wanted it over. I wanted to be everything he wanted. My mind was racing so much I opened the wrong drawer twice trying to get my vibrator.

When I climbed on the bed I shaking. He rubbed my breasts and arms as he turned me around and pushed me out into the bed. He pulled me arms around my back and told me to hold myself open for him. The lube was cold and it felt like he was using half the bottle. I was going to make a snarky comment, but then I felt the pressure of his cock against my skin. I knew there wouldn’t be the slow entries that I had given myself with the plugs. All I could do was relax as much as possible as he grabbed my hips. I took a sharp intake of breath as he pushed his tip in an squeezed my hips with both hands.

“There’s a good girl. See, what did I tell you? If there’s no way, create one.”

Wicked Wednesday for post Stockpiled Cravings

Perfect Evening

Connections are fleeting. Great sex, a lovely cuddle, they don’t last forever. So, not only do you appreciate them while they happen, you cherish the memory of them.

Last night Sir was in a giving mood. We talked about some Sub issues that I have been having. Before D/s I had no issue flirting and very openly letting him know that I was eager for sex. But now I feel weird even playfully flirting with him. He listened patiently to my ramblings and then calmly explained that he didn’t mind my open flirtations. It’s still his call about whether he takes advantage of my offerings or not. So it’s okay.

And, after being turned to a gooey mass by his expert tongue, he told me that he was going to have my ass. I’m actually really getting turned on by anal. The prude that my parents tried to create in me has made it a struggle to enjoy things previously considered off limits. Even so, in my post-orgasmic state I was happy to do whatever he said. I have obviously been a very good girl lately because he even let me use a vibrator on my clit. A girl never feels more loved then when they are allowed to use a vibrator during anal. Trust me, it’s a fact.

So, amazing oral and vibrating anal done, we curled up in a puddle of naked and fun fluids. And we talked about college. We remembered all the great food at the dining hall. The nights when we lived with his mom right after college and we would sneak out (even though, as adults we didn’t need to sneak) late in the evening to get fast food. And he looked at me, and I looked at him,

“I’m starving”.

“Me, too”.

“I’ll go to McDonald’s, you get Bob’s Burgers cued up on Netflix”.

“I love us”.

“I love us too”.

It may not seem romantic to everyone. It may not be kinky enough for most. But it works for us.

Popping the Cherry

So I lost my anal virginity last night. Is that a thing? I’m sure it’s not. And those of you that have been doing this for a good decade or so will just laugh at this milestone. But for me, this is a big deal. I’ve been training for a few weeks now. Sir has been pushing me quite hard. We were going to start earlier in December, so I could be ready by 2015, but life happened.

I was just excited that it didn’t hurt as much as I thought. It actually felt pretty good. I don’t know what that says about me. That I was silly enough to think that it would hurt, or smart enough to be happy that it didn’t.
So that was my Friday night. Several orgasms and my first anal intercourse. Hope you all had a nice night too. I’m looking forward to the rest of my weekend. We’re staying in as it is still negative temperatures outside and in the forecast. After a few job applications I am hoping to curl up with a book and some coffee. Baby cuddles and quickies sound like my perfect Saturday afternoon.