Recently, Alex expressed interest in being fucked in her pristine, virgin ass. I immediately began helping her learn how to have anal sex safely, and if you’ve ever seen Alex’s ass, I think you’d agree I’ve made the right decision.

The secret to happy anal is patience. Take everything slowly. (That, and use insane quantities of lube.) Alex started small, with a well-oiled fingertip placed just inside her anus. Over the last several weeks, she’s worked, moaning and begging, up to the point where she’s ready to try something a little larger.

About a month ago, I presented her with an Njoy “Pure” medium-sized plug. It’s a luxury toy, made from surgical steel about 1.25″ at the widest point, and heavy. Alex went crazy for it, and I’ve slid it into her ass at every opportunity since I brought it home. I’ve even started calling her from the office late in the day and having her put it in for when I return.

I just ordered an anal “training kit,” a set of three cock-shaped plugs in small, medium and fucking large sizes, along with some nice anal lube featuring a mild numbing agent. Alex will be taking the first of these into her snug butt in the next day or two, and has been begging to get through her “training” as soon as possible. I plan to help her celebrate her graduation, personally, sometime very soon. I’ll keep you posted.

As promised…
We’d fallen asleep about 2 hours before after a fairly marathon night of new toys and hard sex. A pay channel was playing on the bedroom TV and the sounds of serious porn humping woke me just before 3 a.m. I looked over at Jack. He was quiet, shirtless, asleep with a little smile still lingering at the corners of his mouth. I could smell his musk. I picked up his arm and curled in under it, with my head on his chest. He wrapped his arm tightly around my shoulders.

Usually, I am not the one that is the most interested in spooning through the night. I was never a cuddly girl and I never forced people to stay after sex. I tend to sleep cool, wearing very little and often with my legs exposed. Having someone against me is not conducive to cooling. Jack is a furnace of heat all day and night.

This time, I wanted more body heat, I wanted to be right up against Jack. I fell asleep.

Not too long after I woke to find my hand was working his cock through his thin pants. He had his head back, eyes closed. He was moaning quietly. I had no idea I could do that in my sleep. How awesome is that? I slipped my hand inside and wrapped my hand around him and began to glide it up and down. He was very, very hard. I woke up completely and became very excited.

I had to get Jack’s cock into my mouth. I absolutely love to suck him. He helped me slip his pants off and I practically dove onto him. Pre-cum was waiting for me at the very tip. I ate it happily. He moaned. I played with the tip, running my tongue slowly down and all around the base of the glans. I closed my lips and pressed them to the tip, making it force them open. I also gently nibbled and sucked the underside of his shaft, down to the base. To tease, I will slowly lick, as if he were made of ice cream. Then, I stay at the tip until I sense he can hardly stand the wait. Without warning, I suddenly plunge his shaft deep into my mouth, sucking hard. At this point he usually moans loudly and I feel his cock throb.

This time, I managed without any difficulty at all to take all of him into my mouth and throat. I have often come close, but never made it all the way to the base for long. I usually have one hand as a ring at the base of his cock working up and down with my mouth to make up for my shortcoming. Not this time. He gasped. I tried not to smile and had to moan for joy myself. I sucked hard, running most of the way up and all the way down his length. With my hand I massaged his balls. He was thrusting into my mouth, gasping, moaning, breathing in long, uneven sighs. He shot his load so hard it went down my throat without my getting much of a taste of it. I felt the warmth as it ran down my throat, making me swallow and suck harder. I was perpendicular to him. He was working my soaking wet pussy with his fingers and I was pushing against his hand. I hardly noticed my pussy until this moment, as I was so engaged with sucking and deep throating. I continued to suck and lick him a little as he came down from his orgasm. We both collapsed, me tucked under his arm again and we slept.

In the morning, he kissed me. He was wet from his shower but stopped to lean over me before dressing for work. He said “if you need to, wake me any time.”

I had an incredible night. At one point, Jack was working between my legs as I lay in the bed and started to ask me questions about my previous partners. Had I ever done two men at once? Well, sadly, no, although I have had three partners in a 24-hour period of time. I know, bad girl. It was college, and it was early in a semester, when I had some time to date before classes got too demanding.

Here’s more detail:

I had a date Thursday night, where I spent what was left of the night at his apartment. This was a young dark, curly-haired man from an anatomy class that I talked with in other classes. He was not typically my type, medium height but a bit too muscled. We had always had witty, sexy banter in class, which I think finally won me over. He won this date by cornering me near the door to class, pressing me against the wall and planting a very passionate kiss on me. He then just said, “I would like to see you after class.” I breathed “How soon after class?” We met late that evening, saw a movie where we started petting and went back to his place. The sex was for me somewhat uninspired, despite the overall arousal and urge to finally “do it.” He was a missionary-only guy and he asked too many “do you like that?” questions and made too many answers for me, “Oh yeahhhh, you liiiiike it.” He was an overt approval seeker. I wanted at one point to say, “I am laying here in your bed, wet and humping, aren’t I?” We did have a little early morning quickie which has it’s own charm and where he refrained from the chatter.

I left for home to shower and get to class. I had a phone call and made a date with someone else that evening (Friday). I had decided to take his last-minute offer instead of going to a party. The second date involved a quick dinner and a rush to get back to the apartment. We got into my apartment, closed the door and did not even make it out of the living room. I think that the fucking from the night before had me ready to go and I am betting I was pouring out pheromones. This guy was much more exciting overall, a physics major. We had not had a lot of time with each other, but the need to fuck was pretty on-the-table from the first time we talked high-energy particles (he had not talked with a girl about it before). He was a good conversationalist and I liked talking science with him

The sex with him on top and then me on top, feet flat, as he sat on the sofa was rushed. He was not a chatter guy, but his hands never stopped moving the whole time. It was a little ticklish, really. He was also a compulsive tit squeezer. He was cute and geeky without the lack of style, but a little too thin and blonde to completely drive me wild. But like pizza, even if it is not the best, sex is still pretty good. In his overall rush we finished pretty quickly (who knows, maybe someone else was waiting at home). I thanked him for a lovely time and sent him home and he did not argue.

I showered again and went downstairs to do some weightlifting. My long hair was loose and wet, bangs in my eyes and I was wearing a low-cut bathing suit/cut off jeans shorts, with no side seams up to the waist band. Everyone in the building had contributed some effort to turning a room in the basement, next to the washer/dryer into a work out room. I did some light stretching and easy sets to warm up on the free weights. I wasn’t looking to muscle up, but to keep tone and flexibility. I decided that my back and upper arms could use a little harder work out and I locked the weights on to the long bar at the bench. I also liked putting very heavy weights on the bar and stretching my legs and lower back by basically folding in half and wedging my ankles under it, one at a time. Basically an upside-down set of splits with more resistance.

One of my neighbors walked in. He offered to spot. We did date periodically and had for about 2 years. He had moved to the building a few months after I did. He was shorter than my usual dates and his already thinning hair was not dark enough for my taste, but he was lightly muscled, decently endowed and not too thin. His overall aggressive but non-violent nature was attractive to me. He was studying marketing and law at the time, although something about him was always intimidated by my advanced science/medicine major. He complained that when we were out with friends and we started talking about those things, that he could not keep up. It overall meant for me that although we were friends with benefits, we’d never have a serious multi-dimentional relationship.

As I finished stretching, admittedly a series of positions that have to be pretty provocative to a guy, he helped me reduce the weight on the bar for a few lifts. When he took position over my head, I noticed he was sporting an obvious hard on. I lifted, a couple times, keeping my eyes on his crotch. I lost the ability to think clearly. He was definitely aroused. I put the bar back and just looked up at him and smiled. Once he realized I had stopped and moved his eyes from my tits to my face, he did not need another invitation. He came around to the end of the bench and straddled it, between my legs. He undid my shorts. I sat up, kissed him and stood, and removed the shorts and bathing suit. He removed his shorts which had a condom ready in the back pocket (my kind of hero). I lay on the bench again, and held the bar. He set to work fucking me hard on the bench, he was kind of standing — no foreplay needed. We went for a long time, and at one point the bench was suffering from the unusual end-to-end torque. We finished, standing up against the wall, me facing the wall and him behind me (think police pat down). After my other dates, I enjoyed that he was largely quiet other than appreciative moans, groans and heavy breathing and not overly grabby. He leaned against me and whispered an offer to come upstairs and spend the night. I turned around, leaned back against the wall and thought about it. I then gave him a kiss, thanked him and said “I need sleep, perhaps tomorrow, and thanks for the spot.”

I heard the boys downstairs the next day, repairing the bench. I wonder if he explained how it had been damaged (probably).

Maybe Jack will be compelled to tell of some of his hot tales in college. I don’t think I have ever met someone with such an easy time picking up women. I remember before we ever dated, wherever we went for a while, there was yet another girl that came up to complain that he had not called her…

More later.

I have never fully explored anal before. I know, another way in which I am still a virgin. The idea clearly makes Jack very hard, so I am working towards the day that I can swallow his large cock all the way into my ass. I imagine he will have a hard time holding on the first time, as I will certainly be incredibly tight. Jack bought me a medium-sized metal plug (njoy) and some lovely lubricant to start. It has a very organic shape, similar to the tip of a penis. I have to say just thinking about using it makes me very close to an orgasm. The sensation is mind-blowing. Every one of the pleasure nerves associated with sex seem to be stimulated with the weight of the njoy and a few new ones, too. The process of inserting it is almost too much pleasure to bear at once. When my ass feels filled by the njoy and he also fills my pussy with his fingers, mouth or cock, I can’t stop coming. It is especially good when he takes me from behind as each thrust pushes against the njoy. Well it is also good with him on top, Oh and then there is the extra stimulus of a mouth on my clit and fingers in my dripping wet pussy… oh it is all good! Even after we remove the plug (an event worthy of another orgasm itself), I tend to have spontaneous orgasms for quite a while. Soon, I will be ready for the large size. Then, ultimately I will be ready for the next size – him. I will have him enter me and I am sure we’ll both explode immediately. I can’t wait. I’ll let you know…

More later

I had lunch with Jack his office recently. As much as we would have liked to, we really did not have a chance to fool around. I found myself driving around all aroused thinking about him. It occurred that I had to have some interesting facial expressions while I was driving. Sure enough, at a light I was listening to a very sexy song and wiggling in my seat. I had my hand in my hair and my head thrown back with my mouth open. I realized I was being watched by people on both sides, a utility truck driver and a landscape crew. I blushed and got back in control of my public persona

More later.

Jack made a stop to bring home a new friend last night on his way from work. No, not a person you naughty thing, but I like the way you think.

What he brought is about 8 inches long, quite thick, and does tricks.

It is clear, with intriguingly industrial works visible inside. At first glance, it is intimidating. For shape and texture, it does a nice job of roughly approximating a good-sized, hard dick. I did mention regret that the tip has no indent/hole where you can put your tongue to gently probe and lick up pre-cum. The head has the nice penis tip, there are “bumps” for G-spot stimulation. The central shaft has spinning beads and then at the base a “rabbit” extension complete with little ears to reach out and tickle a clit. For tricks, the top half of the main shaft has this hula-like rotation (with three speeds), and/or you can set the rabbit to vibrate (three speeds). It was, of course, a Rabbit G vibrator.

I have had a only little vibrator experience. Not so much on my own, but as a sex aide. One ex used to use this contraption that strapped to his hand. I can’t say it felt bad, as it made his fingers vibrate, but it also got hot and I had to be careful not to get burns on the inside of my thighs. I have also had several insertion devices over the years. I am finding that to successfully masturbate, I need good penetration. Just playing with my hand just will not do. My fingers are too small and I have to be sitting up to insert them. Stimulating my clit while something of girth is penetrating me makes me instantly crazy.

Later that evening, we unpacked the toy (and destroyed the package before recycling). Jack made me put in the batteries he had given me at dinner as a little hint something was coming up later. I set the toy on the coffee table to look at it for a while. I picked it up a few times and checked it out. It was nice to imagine what it would feel like.

Jack admitted that he has been wanting to watch me masturbate. He was clearly setting up for a show and he covered up the sofa and got out some lube. I prepared myself. I have to dress up if I am the entertainment. I put on a short, tight, black satin nightie, no undies and shiny platinum stockings. I also pulled out some of the new jewelry, especially for my wrists, as they were going to be very close to the action.

As it turns out, he wanted to start me with it. I half sat on the sofa with my legs pretty far apart. One foot on the sofa, one on a leather footstool. He lubed the tip and put it inside of my pussy. He turned on the controls. It was like an electric shock. The size of this vibrator was enough to make me want to instantly start humping. The movement made me freeze, arched backwards in stunned bliss. It was almost too much to bear. I could not handle the highest speeds, yet. Even just the vibrate function set the lower half of my body tingling. Vibrate did not just make the ears of the rabbit move, it tantalizingly made the whole shaft alive. It did not take long for me to start coming repeatedly. I grabbed it myself and started playing while he watched. I moved it in and out. The tip has enough of a flare, like a real cock. I always have had a thing for that sensation when my hole is spread by a head of a cock and then closes a bit just after the tip to drag, slowly forced open again to accept the rest of the shaft. I love when the first penetration is slow enough to feel every inch of this. Sometimes Jack will stop in the middle of sex as I am about to come again to torment me with achingly slow penetration. I get instantly quiet and lay still to concentrate on feeling every bit of his shape as it moves in and out.

I got used to the slower rotate and vibrate sensations and Jack took over again. After I came again, he removed the vibrator and came in for a little taste. I was instantly completely crazed. The vibrator had left all of my nerves singing and any new sensation was increased in intensity. He pulled down his pants and entered me, and we fucked very hard. Most of the time, he was holding my wrists down over my head. We moved to the bed and he bent me over so that he could finish in me from behind. I was so wet it was running down my legs. We went for so long that we were both drenched in sweat and panting. He in an earlier post mentioned that while I was laying next to him recovering, ass in the air, I asked for a nice spanking. He kindly made sure I had a tingle there, too. I was sated, tired, but also left just a bit horny for the rest of the night. Maybe I will write later about how I woke him up again at 3 a.m. I am still a bit tingly all over. My ab muscles feel tight.

More later.

Where is the most naughty place that you’ve had sex? We have a few. I don’t have an overwhelming fantasy to do it in a public place, but sometimes we just could not help ourselves. On one occasion when I was in grad school, Jack and I were working on my little red sports coupe in the communal garage below his apartment. I could not afford to have the repair done for me, so I got to know that troublesome car really well.

Jack came up behind me as I was bent over the engine, attempting to reach for the top bolt on the starter motor. Without a word he reached around and undid my jeans. He expertly slid the jeans and my panties to my knees. Without hesitation, I was pressing back against him. I don’t know if I dropped the tool or not. Those days, there was so much heat between us that if he was near me, I was constantly juicy and ready. I probably had my ass in the air moving seductively as I worked without even thinking. I have also been told that my ass is one of my best attributes.

He quickly undid his own jeans and thrust inside of me. At some point, while I was there with my eyes closed, moaning and getting rigorously boned from behind, someone walked into the garage. We heard the door at the other end. It was far enough away, from the other side of the car, that they would have had to stop to look to see what we were doing, but after a few moments I am sure the sounds of sex were unmistakable. I can be quiet, but it was so hot and horny, I am not sure that I tried to be quiet just then. Jack thinks they watched for a while, but he was too distracted to look. I never opened my eyes. The college marching band could have worked past us and I think I would have asked “did you hear music?” We continued unabated until we both came violently. We dressed and fixed the car, stopping occasionally to grope, grind against each other and kiss (I can hardly keep from lowering myself on to his lap when he is working under a car).

The first time I fucked Alex was also the first time anyone had ever tied her up during sex (it was also her first spanking and the first time she’d ever needed to get permission for her orgasm, but I digress). Bondage (the “sensual” kind, not the torture kind) has been high on my “favorite kinks” list almost since I started having sex. Our first sexual encounter was (very!) spontaneous. At the time, I wasn’t expecting anything like the night we had.

We’d started out with fairly conventional (if explosive) fucking, me on top, followed by her climbing onto me and impaling herself there. Alex is very short, and at the time was a petite thing. She discovered that once she’d taken me completely inside her pussy, she couldn’t really move up and down much – her knees didn’t reach the mattress. She was just stuck there, filled to the bottom with my hard-on. Not a bad situation; if there’s one thing I enjoy, it’s a hot blonde marooned on my cock. I decided to take it a little further and see how she’d react to being really stuck.

Gently, at first, I pulled her arms behind her back. Initially, she misread the body language and thought I was trying to roll her off of me, until she realized that the reason she couldn’t roll anymore was that I had clamped her wrists together behind the small of her back with my left hand, and my right was pulling her face down close to mine. She figured it out at that point, and tested my grip, flexing her arms but getting nowhere. I remember holding my breath a little, thinking that if she didn’t share my tastes, here’s where I find out.

Alex moaned, long and low, and came hard.

Keep in mind, this was our first time together, not too many hours after our first kiss. For all I knew, she might have done all of this before, but I had no idea where her boundaries were. Still, I believe when life hands you a moment like this, you should you grab it. I decided to keep going until she showed some sign of hesitation.

She’d been wearing this huge silk scarf, now fallen on the floor next to the bed. While she was finishing her orgasm, I snagged it and quickly tied her wrists together, crossed diagonally behind her. Alex is one of those women who has strings of orgasms, one leading right into the next, and that’s exactly what happened for the next few minutes.

Tied now and lost in her orgasms, she wasn’t really in much control. The way she moved her body was pretty much up to me. I put my hands behind her head, fingers tangled up in her curly hair, and kissed her. I could feel the tension in her shoulders with her arms tied back. Her huge tits were dragging up and down my chest as I rocked her body up and down mine, bottoming out my cock deep inside her with each thrust.

She started to come again, but this time was different. Early in her orgasm, I started rubbing her ass with both hands, and as she started to peak, I spanked her once, hard. Alex went crazy, moaning into my mouth as we kissed, trying to pull my cock deeper inside as she moved. I spanked her again and again, more gently (but thoroughly), until she came off the peak of her previous orgasm.

As she started winding up for the next one, I whispered into her ear that for the rest of the evening she needed to ask permission before she could come, or risk some unspecified punishment. She responded by starting to beg wildly, gasping out the words “Please, please, let me come!” between moans and deep, hot breaths. So much for hesitation.

At this point, I’d like to introduce a theory of mine. My theory is this: your body deliberately limits the strength of your orgasm to keep you from straining a muscle or otherwise damaging yourself. I believe that if you’re restrained, something happens in your brain to remove that limit, allowing you a more powerful and overwhelming orgasm. Combine that with the out-of-control, no-limits sense of submitting yourself to someone else and you’re into yet another whole new level of orgasm.

That’s where Alex found herself that night. We fucked like that for another hour, Alex coming continuously. Eventually, I started to worry about her shoulder muscles, and so I finally let myself go, filled her with cum and rolled her onto her back. She lay there in the near-dark, covered in sweat, flushed, her hair a ruin, her blue eyes shining with a happy-crazy gleam, hands still bound behind her.

Not even the first time we fucked was I ever in a rush to untie Alex. I rolled her onto her stomach and ran my hands over her (pink!) ass, lingering between her thighs, watching her spasm as I brushed her swollen pussy. I think that’s the moment when I realized that I could be sexual with just one woman for the rest of my life. After a few moments drinking her in, I turned her loose. She lay there, spent, and promptly passed out while I rubbed her back.

It’s been almost twenty years now, but the passion of that first night always comes back to me in a rush; the spontaneity, the improvised sex toys, the willingness to abandon yourself to something totally new. These are what keep marriage hot. Let yourself be crazy for each other! Trust me, it’s so worth it.

I bought some sexy jewelry and stockings today with Jack, it was spontaneous as we were actually at the store for unrelated stuff. I happened upon some adorable hair ties with star jewels. They make for very cute, attention-getting pig tails. There was also a stretchy, sequined headband that immediately made me think “choker.” I held it up to my neck and turned to Jack. He got that little smile that said he was pleasantly surprised. After that store, I mentioned a desire to get some cuffs for my wrists. We were on our way to the grocery store. He quickly turned the car around and headed for the mall. We found tight, sparkling cuffs for my wrists, pearl bracelets that interlock intriguingly and could easily become anklets, very attractive earrings, a pearl and silver chain that is long enough to use anywhere and a very sexy choker. The stockings included the standard black fishnet and black, white or sheer sparkly thigh-highs with lace tops. He had an afternoon of erections as I tried things on for him and asked him for his input.

Later, Jack read a bunch of my writing and stroked my leg. We were on the couch, a bit tangled. Stripes was on the TV. “Chicks dig me…” I was hoping Jack would have some posts to add. Instead, he closed the laptop and put it away.

He turned to me and looked me over, intently, from across the room. I had discovered that my pig-tail holders made a very cute anklet, I was wearing the cute earrings he picked out and I was trying out the new sparkly wrist cuffs. My awesome bra had my breasts up at attention, my head was all messy blonde curls. Half laying there in the corner, in a pair of short shorts and a silky v-neck T, I suddenly felt very self-conscious under his gaze. A bit like prey. He made a deep growly noise and an exhale, nnnnnn. He walked over, climbed on top of me and kissed me very hard, forcing my legs apart with his body. He slid down, kissing along the way to land between my legs, he grabbed my thighs and easily pulled me down the sofa a little. My shorts were discarded. He then went past my pussy and kissed my leg, my ankle, and the very inside of my thigh, right next to my lips. I was shuddering with desire. He pulled aside the fabric of my soft, lacy, very sheer pink panties and began to kiss, then lick, then eat my pussy with enthusiasm. He teased my clit, he sucked a little and stopped, he ran his tongue around and then when I just couldn’t take the teasing, he would bury his face in and eat. My mind was instantly gone, as was any self-conscious thoughts. Soon the panties were in the way. He threw off his own pants, pulled me up his thigh and half standing he thrust his enormous erection inside of me. I was being pushed into the corner of the sofa, my hands flung backwards, holding on to the arm with my breasts up near my chin. He pounded me with a look that said he meant serious business. He let out a deep, primal growl that made my heart skip a beat. I just wanted more, deeper harder. Pretty soon my legs were in the air, as far apart as the sofa allowed, hands holding my ankles so that I could take him even deeper inside. We came so hard that I saw stars for a minute. I was completely filled with his cum and completely happy.

Jack looked down at me, looking no less predatory, and said “Now, I can concentrate.”

I really like to be “taken.”

More later.

Staying married takes work, but years of hot, sweaty, nasty fun make it all worthwhile. Tune in soon and we’ll talk about how we manage to keep it going.