Reconnecting with Rene

About three months after I fulfilled one of my wildest fantasies by fucking Rene, the older woman who had been my boss for almost three years, I had the courage to share with her an even wilder fantasy of mine, albeit indirectly. I had posted a story that depicted my dream of having sex with my older supervisor in her office more than a year before we actually had sex for the first time, and, as a result, I went back and forth in my mind as to whether or not I should share that story with Rene.

The main reason for my hesitancy was that the story ended with a double-penetration threesome session, and, obviously, I wasn't sure how Rene would respond to that part. Anyone who reads my work knows I'm a fanatic of double penetration, but Rene didn't know that fact about me yet. However, after a few months of enjoyable sex with my former boss, I decided that, even though the intercourse was really hot, if I was going to continue this casual relationship, I might as well go for the fences. If I lost Rene over it, well, I had never intended for this fling to go on forever anyway.

I emailed the link to the story to Rene, and she read it that very night - and followed up by reading all my other work. It was no secret to her any longer what my biggest turn on was. Naturally, Rene commented on the dominant theme of double penetration in my writing, which led to a conversation of some of my experiences and fantasies. The fantasies part inevitably led to my confirming that one such desire was having double penetration sex with Rene.

Rene went on to tell me that she was no virgin to group sex. In fact, in college, she was often fucked by three or four guys in one session, often split-roasted by two men at once. However, double penetration was something that she had never tried and was never really brought up when she was a young adult. Of course, I asked her if she would ever be willing to try it, and my heart practically stopped when she said she would consider it. It wasn't a yes, but it was good enough for me for now!

Over the next five weeks or so, not only did the idea of a threesome not come up again, but my conversations with Rene became less and less frequent and, as a result, our sexual episodes suffered the same fate. I feared that my sharing my fantasy with her was so off-putting that I had irreparably damaged the relationship. Like I said, I had been prepared for that scenario, so I didn't take it too hard. I didn't miss her quite as much as I was disappointed at losing an opportunity to live out another fantasy that just a few months ago seemed utterly outrageous.

Then, around 9 pm one Tuesday night in late August, I received my first text from Rene in at least three weeks: "I hope you're free because it has to be tonight." I may never delete that text. Vague though it was, my gut knew to what she was referring.

"I'm free," I texted back, even though I was planning to go to bed in less than an hour because I had work the next morning. I sent those two words to her as quickly as I could to do my best to prevent this wonderful turn of events from occurring. Then I texted her again, "Free for what?"

"Double," was all she wrote back. It was all she needed to write back. After confirming Rene's house as the location, I was dressed and in my car within five minutes.

It was almost 9:30 pm by the time I got out of the house. I knew I was going to be exhausted in the morning, but there wasn't a scenario I foresaw that wouldn't be worth being less than sharp at work the next day. Fortunately, being later at night, traffic wasn't bad at all, so I was at Rene's house in less than 15 minutes. As soon as I pulled into her driveway, I texted her to let her know I was there. When I got to the door, I was greeted by a middle-aged man.

I'm not sure what I expected, but I was a little taken back when I saw the guy who was obviously the participant tonight. It hadn't crossed my mind that he would be more Rene's age, as he was clearly in his 50s. That's not to say he looked like a wreck or anything. Actually, he was clean, well groomed and I could tell he worked out. I'd just never had group sex with an older participant before.

The man introduced himself as Rene's friend Rob, and I greeted him in a similar fashion. I had to give him credit for being a lot less awkward than I was. I had a lot zipping through my mind, not to mention that my body was calling for sleep.

Since it was already almost 10 pm on a work night, we didn't have much time to waste. Rob welcomed me into the house, and just then, Rene came around the corner down the hall to greet me, a big smile on her face and a long pink robe covering the rest of her. I hadn't seen her in almost three weeks, so feelings of fondness and excitement swirled within me as I greeted my mature lover with a peck on the cheek. A few months ago, even after having sex with Rene, I was uncomfortable with other signs of affection, since it wasn't really affection I was going for but rather pure, depraved lust. However, over the course of time, her and my sessions grew more and more intimate, making me more comfortable to be a little more vulnerable with her while still basking in the depravity that was our fornication.

There, Rene explained to me that Rob was a friend she had met about a month back and had started going out with recently. Her time with him had caused her to not give as much attention to me as a result, figuring I'd understand since our relationship was strictly a carnal one. She needed something more than what I was willing to offer, which I understood.

Rene still, however, craved the attention of a younger man. It was only a couple weeks into her budding relationship with Rob that Rene brought me up and the fact that we had started sleeping together occasionally. Apparently, Rob understood Rene's need for fresh blood, and it was at that point that Rene brought up the next logical step and my longing: a threesome. Rob was game, so with two willing participants, Rene figured she had every reason to finally give double penetration a try.

I couldn't even process my thoughts and feelings as the three of us headed upstairs to the bedroom. As we passed through the door to where the scene of the crime would be, Rene clarified that her daughter was out of town for this one more night and then would be living at home for an indefinite amount of time. Coupled with the fact that she wasn't always in the adventurous mood to try something new and just so happened to be in such a mood currently, it needed to be tonight, sleep and work be damned. No one was complaining.

I could hear my heart pounding in my ears as Rene welcomed us men to undress. I blocked out all the nerves and the anxiety and instead focused on the reality of the situation before me. It had been incredible that I had gotten to fuck Rene in the first place after fantasizing about it for years, but now I was going to fulfill my utmost fantasy involving her by double-penetrating her! The only thing that could have made it hotter was to have done it in her office when she was my boss in the past, but that ship had sailed.

Without giving it too much thought, I took off all my clothes, and Rob and I were immediately sporting hearty erections as we anticipated what was to come. Rene was visibly excited as she sat on the edge of the bed and watched her young stud and her older man get ready to share her. I bet she figured her days of being desired by multiple men were ancient history, but tonight would prove that it's never too late.

Rene stood up and pushed her robe off, revealing the lingerie she was sporting. Like I've said before, there wasn't anything about my old boss physically that initially attracted me to her, so three years ago, I may have balked at this sight. However, having long since developed a very real respect and attraction for the mature lady, not to mention our recently developed sexual relationship, seeing Rene in black knee-high stockings, attached to a purple thong and garter belt, with a matching purple bra added to my excitement. The bra was especially noteworthy, as it cupped her small but round and full boobs perfectly and created a surprising amount of cleavage.

However, there wasn't much of a need for Rene to have been very careful with her choice of attire because, once she gave us the word, it was off her in a heartbeat, save the stockings, which Rene said would increase her chance of an orgasm if left on. I didn't protest; she looked quite good for an older lady with her knee-highs on and the rest of her mature body exposed. Add the fact that this woman once hired me and used to sign my paychecks, and I was as turned on as I needed to be.

Next, Rene asked Rob to turn out the lights, leaving us in darkness once we had all seen each other naked. It was beautiful summer evening, though, so the window was open and allowed some light from the street to come in, making it easier to see well enough once our eyes adjusted. Adding to the atmosphere of this lovely summer night was the oscillating fan that blew gently on us in that quiet room as well as the slight breeze that came in through the window and slightly rattled the blinds.

We quickly discovered that even though I was the youngest one there, I had the most experience with group sex, or, specifically, double penetration, so the older couple was going to rely a lot on my expertise, as silly as it sounds. I knew we would have to go slowly at first and use plenty of lubrication. Also key was for Rob and me to play with Rene for some time to get her fire going, ensuring she was good and turned on before we got to the main event.

To that end, Rob and I lay Rene out on the corner of the bed, having her rest on her back with her legs hanging off the one side while her left arm rested on the foot board. With everything above her knees exposed and a huge, albeit potentially unsure, grin on her face, Rene spread her legs and looked at Rob, then me and then back at Rob as she awaited our moves. I was going to make a move for Rene's pussy, but Rob happened to be closer and got there first. Therefore, I leaned over the foot of the bed and squeezed Rene's left tit as I drew my head near it.

At his end, Rob had squatted at the side of the bed, his mouth now level with his lover's pussy. Staying focused on my part in the foreplay, I put my mouth on Rene's nipple and began to swirl my tongue around it, that movement alone causing my mature ex-boss to squirm a bit on the mattress and flex her ankles. As I sucked on one boob, I squeezed and rubbed the other with my hand. Just as I got going, Rob began to each the bitch out.

Rene groaned, kicking her legs out as she was orally pleasured at both ends. I could only assume this treatment was getting her nice and wet, and she would need all the arousal she could muster if she was going to take two cocks well on her first try. I had faith in her, though, and knew Rob and I together could get the older woman to the level she needed to be.

I didn't pay much attention to what Rob was doing, but I assumed he was fingering and tonguing Rene's pussy, perhaps even her ass, since we would be using that hole too tonight. After sucking on Rene's left tit for a while, I decided to join her in the bed, first straddling over her stomach, my knees on either side of her as I hovered over her, eyeing those boobs that I prized very much. I gave both of them a brief massage in an effort to continue to increase Rene's arousal but then decided to slip my dick in between them. I hadn't tit-fucked Rene yet, so I figured one more first before the big one was in appropriate.

Rene smiled and then let go of the bed sheets to hold her boobs in place while I slid my prick between them, back and forth. All the while, her older pal was still going to town on her cunt behind me, and I could feel Rene's legs kick involuntarily from time to time while her body twitched as well. I would have liked to have fucked Rene's boobs for a little longer than I did, but after a minute or so, I figured there was more I could be doing to prepare her for the main course, so I pulled away and, instead, knelt at the other side of the bed, over Rene's head.

As Rob finished up at his end, I put my prick in Rene's face, and the woman took it in her hand and sucked on the tip, tasting my precum as we waited for Rob to join us on the bed. A minute later, we were all on that piece of furniture and Rene was on her hands and knees between us men as we each prepared to insert our dicks into either end of my old boss. Rene's hands remained on the mattress while I held onto the woman's shoulders and pushed my cock into that wet and willing mouth. Meanwhile, Rob slipped into Rene's pussy and held onto his lover's waist as he began to slowly thrust in and out of the bitch.

For the next few moments, Rene remained in place while Rob and I swung back and forth at either end of our shared lover, each of us guys going at his own pace as we fucked our respective hole. Both of us took just a second to adjust before we just went for it, Rob, I'm sure, being just as ready to go as I was. The only sound beside the fan in that dark, cool room was the steady smacking of Rob's flesh against Rene and Rene's slurping on my cock. The occasionally moan of pleasure from Rob or me or a delightful squeal from Rene added to the soundtrack as well.

By now I had lost track of time and didn't see a clock, but I figured it was time to move to what I had been waiting for, well, years. Without a word, I pulled out of Rene's mouth and retreated toward the headboard as I watched Rob fuck my sexy former boss doggystle for another minute or two before I spoke up and suggested that Rene get on my cock. Rob nodded and slowed down before pulling out, freeing Rene to crawl over to me and then stand up right there on the bed and step over my knees in preparation for the main course.

Dropping to her knees, Rene reached down to grab my cock, which I had been holding at the base while I had waited for her to come over, and helped guide it in line with her pussy. I did quite badly wish to fuck her ass, but I decided that for our first double penetration together, I wanted to be in her twat, even if it meant holding off giving Rene anal until another time. Beside, it appeared I was a little bigger than Rob down there, so it only made sense that I got the hole that was able to make more accommodation.

Rene wedged my tip into her love hole and sank down, the two of us moaning as she did. My heart was tight in my chest as I watched my former supervisor sink down the full length of my shaft as she propped herself up by her hands and knees, the pale moonlight reflecting off her creamy skin. I couldn't believe what was happening, especially as this middle-aged stranger knelt up behind Rene and me as she and I were already joined together. As I worked the entire length of my dick inside Rene's tight pussy, I knew I needed to secure her by her ass and spread those cheeks apart so that my new friend could help me achieve one of my wildest fantasies.

As aroused as I'd ever been, I couldn't help but thrust up into Rene as I held her ass open, at first only slowly sinking my pelvis back before thrusting up into that tight, petite body, but the longer Rob stayed back, stroking his cock and just watching his lady friend take a much younger man's cock, I started to thrust faster and faster until I almost got lost in the sensations of having sex with this older woman in that dark, cool room, all but forgetting that we had convened to be a threesome and not a twosome. Upon catching Rob in the corner of my eye, I recalled why I was this turned on to begin with and decided to slow down in order to initiate the final steps of creating this Rene sandwich.

At last, Rob finally scooted in, pressing his cock against Rene's tight asshole, which I was spreading out as wide as I could. Once Rob had pushed the first portion of his wang into Rene, I let go of the woman's butt and instead ran my hands up and down her back for a moment while more and more of Rob penetrated her asshole. Eventually, my hands settled on Rene's shoulders, where I sunk my nails in as I could feel that thick cock filling the hole adjacent to the one I was inside. Being heterosexual, I didn't need that cock for my own benefit, but being a part of filling a sexy lady with more than one cock was always exhilarating for me.

My breathing grew shallower and my heart was filled with emotions I couldn't even describe as it settled in that, at long last and in the most fortunate twist of fate, my boss (well, former boss) was in the middle of a double-penetration threesome of which I was a participant. Still holding tightly to Rene's shoulders, I pulled the older woman in for a brief kiss as she tried her hardest to not make any noises of discomfort while Rob filled more and more of her butthole until his balls joined nearby mine on the woman's taint.

This night, my relationship with my former boss had finally culminated in her being sandwiched between another dude and me, and as soon as we had her pinned there, we started getting to work, albeit slowly. I think Rob waited for my cue, so I pushed gently into Rene, making her moan softly as I continued to hold onto her shoulders. Then I pulled back, and when I pushed in again, Rob knew it was his turn to pull back. Deliberately and slowly, we men worked our way into double-stuffing Rene on her own bed there, the two of us taking turns going to the hilt inside her, our balls alternating with each other in making contact with Rene's stretched-out taint as we filled both of her holes.

I exhaled deeply, overwhelmed by the sensations of the cool air blowing on our warm bodies in that dark room and the realization that Rene was not only on top of me with my cock stuffed inside her but also had another cock fucking her asshole just as gently and deliberately as I was doing in her twat. The sound of the fan drowned out most of noise, though I could hear the occasional squeak of the bed as Rob and I took turns slowly thrusting into the mature bitch lying between us.

After a minute or two of taking soft pumps from us men, Rene sank her nails into my shoulders and buried her face in my neck for just a moment, but long enough for me to wonder if she was taking the double penetration well. Then, like a dart, her head shot up, her short hair rustling about her face, and she cried out like an animal. The noise was difficult to interpret by itself, but the look on her face, even in that dark room, was one of unmistakable joy.

As I adjusted to the reality of my glorious situation, I was overcome with how good Rene's pussy felt with her ass being fucked at the same time. The pleasure was as intense as anything I had ever felt, and all we were doing was trying to ease her into her most difficult sexual endeavor yet. As the intensity of the pleasure increased, it became harder and harder to maintain a slow pace. Before I knew it, I was pumping faster into that delightful pussy, and Rob was keeping up with me by plugging that tight ass at the same rate.

I wasn't sure how Rene would respond to the sudden increase in our fucking, but she appeared to enjoy it, laughing and moaning as Rob and I sawed in and out of her. Rene propped herself up by her outstretched arms, her hands now back on the mattress as she held herself between our thrusting bodies. The sensations all around me were simply too much for me to stay in control of myself, whether it was the strands of Rene's short blond hair falling in the woman's face as her body bobbed back and forth from the fucking; the jiggling of her perfect boobs right over my face in rhythm with Rob's and my alternating thrusts into the sexy milf; the scent of perfume, sweat and sex all mingled in the air around us or simply the sounds of the squeaking bed and the fan blowing the warm summer air.