Welcome to Rolennia Ch. 02

When Simma undid my last button, I tossed off my shirt. Simma released my penis and spoke to me while stroking it. "You want start usual way first? Or want start right away with butt?"

Simma didn't pull any punches. "Can we start the usual way first?" I didn't want to let on that I was feeling a little nervous about doing this.

"Of course," she said, standing. She slipped her panties down her stockinged legs, stepping her high heels through the leg holes. She lifted her short skirt up to her waist, revealing her smooth-shaved mound and the garter belt holding up her hosiery. I was watching her as I tend to do, so I hadn't moved. Without hesitation she stepped forward, bent one knee and placed it next to me, and swung her crotch over my erection. With practiced efficiency she grasped my penis and guided me into her vagina, already lubricated and ready to go. Ah, to be 23 again--her pussy was wet and ready just from sucking my dick. At first she used to masturbate while sucking to be ready to receive me, but now engaging in intimate acts of any kind were enough to get her juices flowing. I wanted to think that maybe that meant that at some level least she was into me... but I was much too afraid to ever find out for certain.

Simma swung her second leg over, rested her hands on my shoulders for balance and began lifting her crotch and the lowering it onto my penis in rhythm. I straightened my feet on the floor to provide a stable platform and rested my hands on her waist to help keep her torso aligned with my dick as she impaled herself on my shaft repeatedly. It felt a bit funny--not because she was on top, which she frequently was, but because I was sitting up on the bed while she did it. This particular position we usually only did when sitting in my office chair; I found myself missing my backrest.

Simma interrupted my thoughts by wrapping her arms around my neck and bending forward to kiss me again. She did her best to balance continuing to fuck my dick with the necessity of keeping her head still enough to kiss, but I loved it because again she had initiated the kiss. I was already wishing she would come on to ME instead of the other way around every night!

When the kiss ended, our eyes met. "Let me know when is ready to change... I get lubricate." Then she resumed full-bore rising and falling, engulfing my dick with her eager hot pussy. I watched her thighs momentarily, appreciating the muscle tone it required to engage in such aerobic intercourse--she could keep this up for an hour easy if need be.

"I'm just not sure what to do," I confessed.

"Is OK, I teach. You want start?"

"Sure, why not?" I said trying to sound nonchalant. Don't get me wrong--the thought of butt-fucking hot little Simma had me as excited as anyone. But I really didn't want to screw up, not succeed and let Simma down. I expect that any guy lucky enough to have sexual access to a beautiful women 20 years his junior has these kinds of concerns some of the time.

Simma smiled, held my chin in her hands and kissed my cheek before lifting herself off of my dick and standing up. She took two steps to the nightstand and opened the drawer, taking out the silicone lubricant housed there. "You want stand?" she hinted, so I did. She squirted on squeeze of slippery onto her fingers and started to rub onto her butt all around the plug that still filled her. As she worked it in, she knelt and sucked me again, just to make sure I stayed hard, undoubtedly tasting her own juices that permeated my member. Satisfied that my stiff wasn't flagging, she globbed out another dollop into her palm and with expert stroking worked it all around my cock. In no time I was slippery as a greased pig.

Satisfied, she suddenly got up on the bed on all fours. Her knees were just at the edge of the bed, with her calves hanging over, and she lifted her butt up into the air. It was clear I was to fuck her while standing, so I stepped up to the plate so to speak, stroking my slippery staff. Realizing her butt was a bit too high, she spread her knees further apart, bringing her lower. "Just a bit more," I directed. She did, and now her butt seemed to be the right height. "Good," I said. Good thing she was so flexible. And man, is there anything sexier than a girl bending over backwards (almost literally) just to give you a better angle of penetration?

"OK. Now I pull out plug. As soon as I pull out, you go in, yes?"

"Yes," I agreed, mesmerized by the succulent ass before me. I had often fantasized about anal sex, and now with this ass one inch from my dick and about to let me penetrate... any anxieties I had earlier were forgotten in trembling anticipation. Her head was turned sideways as she reached for her butthole. Grasping the plastic plug, she tugged at it, slowly so that her sphincter could expand to let the slightly wider part inside her out. It came out slowly, slowly, until at once the widest part of the plug was free and the rest of the roughly conical plug came out easily. I wasted no time... as soon as the plug was out, I was there, shoving my dick in. My dick sank balls-deep into her anus before her ass could tighten around my dick... but I could feel it tightening quickly. I held my position for a moment as her butt squeezed me tightly. But it reached a certain pressure and then nothing more, so cautiously I tried to slide my dick out.

With my penis so slippery, I had no trouble sliding in and out despite the pressure applied by her asshole. And because it was tighter than a pussy, I found it immensely pleasurable. It took a bit of getting used to the fact that the pleasurable sensations were focused in a narrow band, but my thighs bumping into her taught cheeks with every thrust was a real bonus. Simma arched her back and lifted her head. She even seemed to push back towards me to meet every thrust. I couldn't see her face, so I didn't know if she was enjoying, in pain or indifferent; she said nothing. But with my hands on her haunches, the sight and sensation of my penis perforating her lovely cheeks was quite stimulating. I could see how a guy might get real used to this, perhaps to the point of engaging in anal sex exclusively. Not me, I definitely wanted to fuck her pussy again, but I also hoped this wasn't the only time I'd get to plow this ass. Oh yeah, that's right... I'm the boss and she's the secretary. She'll give me this fine ass anytime I ask for it. What did I ever do before working at Systems International?

Simma turned her head slightly to look over her shoulder sideways. "You like Marteen?" The way she said my name sounded like a double-e instead of an "i."

"Yeah," I agreed lustily, "it feels great." After a pause, I thought to add doubtfully "is it painful for you?"

"Is not hurt, not yet. Is feel funny yes, but no pain."

"OK. Just let me know if it does... I don't want to hurt you, and I can't see your face to tell for myself."

She turned her head slightly around again. "You want see my face?"

I stopped thrusting for a minute (albiet balls-deep in her butt) and said "Ialways want to see your lovely face, Simma." I wondered if that came across as cheesy or romantic--in which case it was somewhat wasted on a girl for whom pleasing my every sexual whim was part of her job. But Simma was on the move... she extracted herself so she was no longer impaled on my dick, did a 90-degree turn and roll, and put her head on the pillow. She spread her thighs and lifted her legs high in the air, ready to receive me... this was a much more common position, and seeing her in that position was by itself a reason for living. I got on the bed and knee-walked to my customary position just below her butt. I noticed that she had rotated her spine up more than usual, so that her knees were closer to her head rather than straight up in the air. Again her hand reassuringly gripped me, and guided my staff towards her asshole. I understood now that she had to lift her butt more so that I could assfuck her while on her back.

I found my way in and started to stroke, but something felt a little different, rawer... "Do we need a little more lube?" I asked.

She nodded nervously "Maybe is good idea." I sensed this was more uncomfortable than it had been doggie-style. I reached for the tube, squeezed some out and started working it into my cock. Simma's hand came out of nowhere, stroking me briefly as well, but then taking the excess lube she had collected and working it into her asshole. It only took a minute and we were ready to try again. She lined me up, a bit gingerly this time, and again I found my way into the dark cavern. There was no problem now, however, with chafing as I resumed my full-on fucking pace.

I watched Simma as I enjoyed the sensations of her tight ass on my dick. She held her ankles in her hands to help keep her legs high, which I found very sexy. Her eyes were closed, however; perhaps she was concentrating on staying relaxed. I liked looking into her eyes when my prick was inside her. Oh well... I turned my gaze to her breasts, her belly, which was scrunched up and almost invisible in this position... hello, now this was new. I guess I hadn't thought about it, but when my pubic bone wasn't pressed up against her pelvis, I could catch quick glances of her pussy. I pulled back and slowed down... wow, that was kind of cool. Her shaved slit, blushed with excitement, lay ready but unused as I plowed her ass. But I also discovered that in order to see her pussy, I had to back way up, to the point that I couldn't get good leverage for doing my business. So it was either watch her pussy or fuck her ass... easy choice. I leaned forward again and resumed cranking away.

When I leaned forward, Simma seemed to be reacting more. This encouraged me to fuck harder, which in turn got an even bigger rise out of her. This was awesome, but I didn't understand what was happening until I paused for a second with my dick deep inside, feeling around. That's when I felt her pushing her mound against me, and I realized that by leaning more forward like this I must be rubbing directly against the bulb of her clitoris in a way I didn't when my dick was in her vagina. So I leaned forward a bit more when I resumed my pumping, and sure enough, Simma was in heaven. She opened her eyes; her face had that wonderful mixture of pleasure and surprise you see when you're really rocking a girl's world. Her ankles slipped out of her hands from the violence of my thrusts; she tucked them around my torso, holding by back lightly just below the armpits. Her mouth fell open and her breathing grew even more salient.

Our eyes met. I kept pumping her with my dick. She kept getting aroused... and more aroused... I knew that look; she was getting close to orgasm. My arms and legs were getting tired, but like a horse chasing a carrot the fact that she was close to cumming spurred me on. Thank goodness it was silicone lube, because anything else would have burned away from the relentless, pleasurable friction. Relaxing was suddenly not a problem, because all she could focus on was the pleasurable sensation of my pube teasing her clitoris while my dick excited its deepest roots that abutted her rectum. She suddenly gripped me more tightly and her eyes glazed ever so slightly; I knew I had taken her to the top. I slowed my pace, waiting to experience the rumbling earthquakes that shook her body when she came from within. I was not disappointed. Her sphincter, however, seemed to squeeze me even more tightly with each tremor. When her orgasm subsided, her ass was really tight... so tight it wasn't very comfortable for me. I withdrew before it squeezed my dick clean off.

"Oh... that I was not expect," she panted, "was very good."

"I love to make you happy, Simma," I replied. She smiled; I bent over and kissed her. The kiss was brief--Simma wanted to get on with business. She lifted her legs again, and I prepared to re-enter her ass... but suddenly it was too tight.

"Oh... I get tight with orgasm," she announced. "I try relax. Maybe get plug again."

"Hold on. That might not be necessary," I said gently. I was starting to understand how to make this work. Simma needed to be relaxed for her asshole to be elastic enough to accept me... and I knew how to make her relax.

She didn't know what I was doing when I moved over and laid next to her. But she quickly got the picture when I gently rolled her to her side. She bent her knees halfway, and I slipped in behind her, mirroring her position. We fit together like two spoons in a drawer. I kissed her shoulder and neck while stroking her arm gently, occasionally letting my hand wander and touch her belly, thighs or breasts, but then returning to stroke her arm and shoulders. This was our usual post-coital position, when we lay in bed in the afterglow before falling asleep. Sex usually tires men but wakes women, so I had grown accustomed to gently caressing Simma in the spoon position to help her relax as well before dozing off myself. It was a very special, intimate time between us, and it really helped build this bond that made me feel like there was more between us than her simply fulfilling her job responsibilities. Simma didn't quite understand why we were doing this already. "Why we do zis now? You not finish."

I propped myself up slightly and whispered in her ear "because it helps you relax, right? And that's what you need... to relax."

She nodded slightly, understanding now. I nibbled on her ear. Her hand reached back and found my erection, still quite aroused. She gripped it gently and stroked it, keeping me hard while I calmed her with my gentle touch. I could feel her relax by the touch of her back against my chest.

I let her keep stroking me while I reached behind me for the lube once more. I squeezed out a fingerful and gently rubbed it around the area of her arse. I even pressed my finger into the tight hole; she didn't tense up at the intrusion. That encouraged me that maybe we were ready to finish this party, so I squeezed out another glop right onto my dick. She felt the slippery stuff and worked it into my penis for me. Then, while kissing her shoulder, I pressed my erection up against her anus. Her hand was there anyway and helped line me up. I pressed my dick against her asshole, and without too much trouble I was able to penetrate her ass again.

I slowly screwed her ass in the spoon position, still kissing her shoulder and neck. She offset her one foot slightly, which made it easier for me to penetrate. I reached around and fondled the closer breast, playing with the nipple that quickly became erect with my touch. She put her hands together and lay her head against them like she was sleeping, except of course that my dick was up her ass. It worked, though--she was relaxed, and so I had no trouble buttfucking her. Spooning, however, does not lend itself well to a fast pace. I loved screwing her ass like this, but I also knew that I'd never cum this way. So after enjoying the leisurely boof for five minutes or so, I returned to my knees.

Simma turned and looked up, ready to move to whatever position I wanted her in. I gently laid my finger on her lip as if shushing her. "Stay the way you are, darling. I think this will work fine." And it did. She laid on her side, head resting on her stacked hands, her butt thrust out in my direction. I was on my knees, fucking her in the ass. Yeah, my body was rotated 90 degrees relative to hers, but an asshole is perfectly round--what did it matter what angle I came at it from? And with the ability to gain traction, I regained the ability to fuck her like an animal.

I suppose it might have looked a little funny; she was relaxing on her side like she was resting, I was screwing her ass like a madman. But it worked; she stayed relaxed, and I got full access to her anus. I also liked that I had easy access to her breasts, and watched my fingers knead them and tweak her nipples while fucking her up the butt. I wished I could see her face, but I could see it in profile, and I could see that she was relaxed and content. That was all I could ask for, really.

I wanted to finish quickly at this point, and so I kept pounding away without letup. She was able to stay receptive, so really we could have kept going this way for as long as was necessary. Only that wasn't very long. Her lean young body laid before me, receiving my erection in her backside... the curve of her thighs... the shapeliness of her torso... the firmness of her young breasts... there was plenty of stimulation. I drank it all in like a desert wanderer, and so it wasn't long before I could feel myself getting ready to explode. "I'm going to cum!" I announced.

I was surprised that Simma jumped into action. She turned and looked up at me brightly. "Try to not cum very deep. I want take picture."

It took a second to understand... of course. She was supposed to provide proof to get out of training. What better proof than to send Ivana a picture of her stretched asshole with my cum dripping out of it? I didn't have time to think any further before it happened. I was still half-in when the first geyser exploded, but whereas I usually like to orgasm as deep inside as possible, this time I pulled back so that just my tip was still in her butt. I exploded two more times like that, and then had the thought to do one better. I got out just in time for the last spurt of cum to splash right across the opening of her ass.

Simma quickly rolled onto her back, lifted her legs high again, and pulled at her ass cheeks to keep her butthole gaping. I quickly reached for my phone and set it to camera mode, then flashed two pictures of her proudly displaying her cum-soaked ass for the camera with a half-smile. I then took a close up. I showed her the pictures, and she smiled proudly. "Perfect! Is done now."

"OK. I'll send them to Ivana," I said, and that's what I did while Simma ran to the bathroom.

When she came back, Simma put her arms around me and kissed me with palpable gratefulness. "Sank you Marteen. Now I not need go train."

"My pleasure. Besides, I keep telling you, I don't want ANYONE but me touching you! Not even another girl."

She smiled almost condescendingly at what she perceived to be my naivete. "You very sweet Marteen. But at convention, you muss share."

I shook my head adamantly. "No way. I am NOT sharing you, my sweet." And we kissed again. I felt like she appreciated my devotion to her; I really treated her like a boyfriend would, and I don't think there was another secretary at SI that could say that--maybe not another secretary in Rolennia. Whether she thought that was a good thing or a burden, well...

"You like very much, I sink," she said with a sparkle in her eyes. "Somesink tell me is not last time I do zis for you."

"God I hope not," I agreed.

We kissed once, then Simma lay back down as she had before. "Massage me again, Marteen?" she asked, almost pleading. I returned to my spoon position as I more commonly did--satisfied and softening. I kissed her shoulder and stroked her arm lovingly until she fell asleep. Normally I was the first one to sleep after sex; I wasn't sure what this meant, but it made me feel good to know that I had lulled her to sleep. I looked at her naked, smoking hot body as it lay next to and up against mine. Resisting the urge to stroke her tits one last time lest it wake her, I reached down and pulled the covers up over the both of us. Then with one last kiss to her shoulder, I closed my eyes and lay down to pleasant dreams... dreams of fucking lovely Simma up the ass again and again...