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Double Trouble

Category: Mature
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I have always had a yen for mature and older women. This was particularly true during my younger high testosterone years. As I have grown older, the age gap of interest has narrowed if only because women older than myself at this time of my life, are often no longer interested in arousal.

I don’t know what triggers my erotic interest in any particular woman. Physical appearance is not necessarily significant although beauty can be a catalyst.

There is just something about older women that has attracted me over the years. It probably has something to do with their self-confidence and the sense that they know what they want.

In the years prior to my marriage at age twenty-five, I had several sexual encounters with mature women in the 35 to 50 year range, and one with a lady almost 60. I don’t recall actually seeking them out. It just seemed to happen and the memories of those encounters still excite me.

And so it happened during my last year at a college located in a small town. I had been going steady with a girl during the last half of the prior college year. Fay lived with her mother Adrienne, a divorced lady with whom I had developed a nice relationship. She thought enough of me to invite me often for meals and she was generally kind and supportive of my dating her daughter. At the conclusion of the school year she had asked if I would like to board with her and Fay the next semester.

I admit to being cautious in my response. Boarding in the home of my girl friend presented some potentially awkward situations. What if we broke up? Would I have to move out and find another place in the middle of a school year? What about sex with Fay? We enjoyed it regularly, but seldom at her house, and then only when her mother was out. We usually made out in my car, or at a motel, or on a beach. But then of course, those options were still open. It appeared to me that it would almost be like being married and I was not yet ready to get married, nor had Fay given any notice that she was considering it.

But I accepted on the basis that meals would be good, I would have a room of my own and I would be close to Fay. I moved in my first day back in town.

Adrienne must have known that Fay and I were lovers and that we had enjoyed naked times together. And although she did not address the issue with me directly, she did let Fay know that we would not be sleeping together. Adrienne dated occasionally and I presumed that Fay and I would find opportunities for close encounters.

All three bedrooms were on an upstairs floor along with the bath and shower room. This was awkward for the first few weeks for Adrienne and I. We had to remember to be properly dressed going in and out of the bathroom.

On the erotic front, Fay and I found some free time together in the late evening. After our evening study sessions, we had the lower floor to ourselves to watch TV. We made out nicely on the sofa, Fay usually sans bra and panties. When that point arrived where closer quarters were called for, we made do with hand jobs. But it was only a matter of time before nature forced us to risk it all.

We were on the sofa one night, ostensibly watching TV. Fay was wearing a loose sweater and flared skirt without underclothes. I was wearing flannel sweat pants shirt and jockey shorts. We were kissing passionately; touching and feeling while keeping our ears open for movement on the stairs.

I had bared one of Fay’s tits and was squeezing and rolling a nipple in my fingers as we kissed. Fay’s hand was caressing my stiff cock through the sweats. She whispered, “Suck my nipple love, it is aching.”

I almost devoured it before lifting the sweater higher to expose the other tit, it’s nipple almost exploding in anticipation. She enjoyed rough nipple treatment, so I sucked and pinched hard with my lips, occasionally scraping them with my teeth. Soon her hand was inside my shorts and around my cock, stroking it slowly with one finger circling my knob. She had become very adept at hand jobs and could anticipate my pleasure.

I slipped my hand down to her knee and pushed up under her skirt and along her inner thigh. She spread to allow me to reach her pussy lips, while still clutching and stroking my cock. My fingers teased her slit and my thumb stretched upwards to rub her mound.

“Baby, you trimmed your bush, damn, feels different,” I whispered.

She bent to my ear with her lips, “Yes, looks neat, I want you to see it, took me hours to do it. Take a peek.” Her breath was coming in short gasps as my fingers squeezed and rolled her pussy lips in preparation to slipping one into her.

I rose up and paused, checking for any sign of movement upstairs. She raised her butt to allow me to roll the skirt to her waist and totally expose her lower body.

“Oh God,” I whispered as I looked down at the beauty of a woman’s soft belly, hips and long legs. And centered in all of that, was the perfectly shaped tiny triangle of dark bush with its trimmed lower point touching the top of her slit. We looked down as I worked one and then two fingers into her. We continued kissing, my fingers producing sticky sounds as they relentlessly plundered her clit and tunnel.

This would normally have been the time when we got each other off with hands and fingers. We had not reached the level for oral sex as a couple but had discussed it several times. She was strangely reluctant to receive it. But somehow, hand jobs would not satisfy us this night and I would not be mounting her on the sofa.

Fay whispered, “The kitchen.” We entered it silently and I lifted her up to sit on the counter top. I pulled her skirt up to her waist while she pulled her sweater off, her lovely breasts tumbling out. I stepped out of my sweat pants and shorts and moved between her legs.

The desire to fuck overcame the fear of being discovered and added a little extra sauce to our coupling. I pulled her butt to the edge of the counter top as she guided my pulsing knob to her very slippery pussy. We kissed to stifle our groans as I eased my cock into her.

I pulled my own sweater off as I continued stroking. I was almost on my tiptoes because of the height of the counter but we were too desperate to stop and adjust.

My initial burst of cum ignited her orgasm and we uttered our first audible sounds as we clutched together on the counter top. We kissed as her pussy contracted to ease my cock out. We laughed softly, amazed at our daring but thankful for the release of tension built up by several weeks of heavy necking.

We agreed that we would have to find better locations in the future to make love, although we were content with the results for that evening.

Gradually, Adrienne and I relaxed as we became more casual about our attire. She was often in her pajamas or nightie in the morning while I often made my first visit to the John in shorts or sweats. Her attitude softened and I could sense her increasing affection towards me. At this point I was not really thinking of jumping her, but I was becoming more aware of her attractive body.

Adrienne was simply a more mature version of Fay, their bodies remarkably similar although facial resemblance was less striking.

Fay’s body was firmer than her Mom’s but having said that, Adrienne, bra-less in pajama’s or nightie, was a delight to view and she seemed quite at ease when she noticed my appreciative glances.

Women of all ages have the natural ability to express emotion with a brief touch of the fingers on any part of a man’s body. Usually it simply means ‘I like you, you are nice’. But depending on the circumstances it can also mean ‘I want you’. This interpretation can be misleading on occasion and cause one some embarrassment, but for the most part I have read it correctly through the years.

I soon came to the conclusion that Adrienne’s touches and glances were of the erotic variety and that she found me desirable. She would grip my bicep as she giggled at a joke. She would rest a hand on my neck as she leaned over to pour me more coffee. Our hips would brush when I brought my dirty dishes to the sink. And then there were the sweet ‘good morning’ kisses, fleeting and yet telling to my fertile mind. All this occurring at breakfast while Fay was still upstairs in bed or in the shower.

We began trying to find ways to be alone for brief moments. I would drift into the kitchen while Adrienne prepared dinner, watching her as she worked, her ass moving, breasts swaying and eyes seeking mine, and always with a soft knowing smile. I would offer to help out, hoping to get close enough to brush or touch her body. She never backed away or tried to avoid contact.

Fay was always the last one up in the morning, and Adrienne and I soon synchronized our own preparations for the day. We timed ourselves to meet in the hallway to or from the bathroom. Her door would be open and I would catch her in bra or panties, she pretending that she was not aware of me gawking at her. I did nothing to hide my morning erection and she checked for it regularly.

I was ready to fuck her if the occasion arose and if she was willing. I had no sense of disloyalty or shame for my thoughts. My only concern was not to get caught with either of them by the other. I suspect however, that Adrienne was wrestling with a different set of concerns. If she had decided that she wanted to bed me, those thoughts were no doubt accompanied by a lot of angst concerning her daughter.

Adrienne was late one morning as I was in the kitchen preparing my own breakfast. She rushed in and told me to sit down and have a coffee while she made an omelet. She was always quite protective of her kitchen.

In her rush, or maybe it was deliberate, she was still wearing her nightie covered with a light robe. I became very aroused at the sight of her breasts slipping side to side and her ass jiggling and trembling as she moved. I could not take my eyes off of her.

She brought my plate over, resting one hand on my shoulder as she set it down in front of me. I could smell her scent. My thoughts were not on the omelet. She brought the coffee pot over to refresh my cup, her hand on my neck, fingers tracing little circles under my ear. She lingered long enough for me to react by reaching behind her to stroke the back of her leg just above her knee. She pressed her breast against the side of my head and bent down to brush her lips through my hair.

“Oh God,” she groaned as I eased my hand up under the nightie between her inner thighs. She shifted and spread her legs a bit to allow the edge of my hand to contact her slit. She pulled my head more tightly to her breast as I caressed her pussy lips, capturing and rubbing them together. I had just eased one finger into her when I felt her body tighten and pull away from me.

“I’m so sorry Jim. I don’t know what got into me. I’m sorry.” She tried to smile it away but her mouth was tight in anguish, and she ran out of the kitchen.

Well, I was sorry too, but soon I began to wonder about the ramifications of what had happened. Were my days in this idyllic situation about to end? My only thoughts were about myself. It would take several years for me to become concerned about the thoughts and emotions of others, especially for occasions involving my cock.

There were no immediate results from this delightful encounter with Adrienne. Fay remained constant in her affection, and we found ways to get alone long enough to fuck away our needs. Adrienne herself had settled down nicely, although contact opportunities were reduced noticeably. Life went on.

And then it began all over again. Adrienne became flirtatious when we were alone. The touches, glances and suggestive comments became the norm once more. I believed that it was just a matter of opportunity now. She appeared to have overcome whatever moral demons she had been fighting and now made little effort to hide her desire to bed me.

Fay was late getting home one day. I was heading for a shower and met Adrienne in the hallway. She smiled and gripped my arm as we passed, turning her face up to me. I kissed her. I pulled her to me, our lips still engaged, her arm circled around me and I felt those great tits rub across my chest. I rubbed my partially engorged cock on her hip and then on her belly.

I grabbed her ass cheeks as our kiss continued, just as we heard Fay at the front entrance. There was no panic or remorse in Adrienne’s eyes as she pulled back, her eyes burned into mine as she whispered, “Can’t wait till next time.” A little peck on the lips and she went down to meet her daughter.

This lust that I had developed for Adrienne had no impact on my relationship with Fay. If anything she became more responsive to my kisses and touches. In fact, that same night I was awakened from a deep sleep to find a warm naked body sliding into bed beside me. I felt a finger on my lips, “Shh, no noise, let me do it.”

Fay pushed me to my back and crawled in over top of me. I was fed one nipple and then the other as her hand worked my cock to full erection. She slid down my body, dragging her hot tits along my chest. I thought maybe she would go down on me, but she raised her butt as she settled her knees each side of my hips and stuffed my cock between her legs. She pushed herself up on her extended arms, with the sheet up over her back and slipped her pussy down around my cock.

She must have felt emboldened being in her own home, as she had seldom been particularly forward. She gradually lowered her upper body as she stroked me. She pressed her tits against my chest as her butt bounced up and down with increasing speed and thrust. She buried her face in my neck, sucking and nibbling my skin as her orgasm began to build. Stifled groans were accompanied by the gentle slap of her belly on mine. I began to come, driving my hips upwards, lifting her entire lower body, but she did not relent, her hips twisting and turning her pussy around my cock until I could feel her ass cheeks clench and twitch.

We lay still, listening for any movements from her mother. I whispered, “Damn baby, where did that come from. Not that I’m complaining.”

She showered my face with kisses and murmured, “You looked as if you needed it, your eyes devoured me when I came home today. She knows we are doing it, so I don’t care if she hears us.”

During the following weeks, Adrienne and I managed to have brief moments together. Breakfast was always a good time. Adrienne was now regularly in her nightie while cooking. I had pretty much explored her entire body under the nightie. I had held her entire pussy in my hand, squeezing her mound with the heel of my hand as my fingers played and teased her pussy. We had almost fucked in the chair one day, she straddling my lap and rubbing her pussy on my cock still closeted in my shorts. But we had not yet consummated our mating preliminaries. She told me that she had a ‘little helper’ in her drawer upstairs. I looked after my problem with a quick shower before leaving for the day.

I was a happy guy and life was good.

It was a Saturday morning. I slept in knowing that Fay had a meeting to attend for most of that day. I heard she and her mother downstairs soon followed by the sound of the garage door opening as Adrienne drove her to the college. I dropped off to sleep again and was awakened when Adrienne returned. I lay there stroking my regular morning erection and wondering if this might be the day that Adrienne and I would end the foreplay phase. If it were to be, it would have to be Adrienne that launched it.

I decided that I would shave and shower since she did not seem to be in any particular hurry to claim me. I returned naked to my room in the hope that she would stumble on me in the hallway and lose control. But I drew a blank. Just as I was pulling my shorts up, she appeared in my open doorway. My cock was halfway into my shorts and I froze momentarily. When she looked down at it, I tucked it all the way in.

She grinned at me, “I was just wondering if you would like something different for breakfast.” Her eyes burrowed into mine. Now that the opportunity was here, neither of us knew what move to make.

I looked her up and down, not hiding my desire in the least and said, “Yes indeed, something different would suit me fine. What are my choices?”

This little repartee ended abruptly, this was not the time to be coy and play word games. We had admitted with actions and words that we ached to fuck each other. She moved towards me as she opened her blouse and tossed it on the floor. She hooked her hands inside the band of my shorts and pushed them to the floor. When she straightened, I unhooked the front hooks on her bra and watched her tits tumble out. I murmured, “my God, they are beautiful” as I hefted them in my hands and rubbed the nipples on my chest. My words pleased her, her eyes softened and she pressed forward for a kiss, tentative at first, then slowly increasing in desire and passion.

She was not at all shy at being naked in front of me, and in fact looked over to a mirror to watch me push down her skirt and panties. Her brush-cut bush was trimmed to a narrow strip of very dark hair, set off by the chalky whiteness of her skin. She posed for herself in the mirror as I stroked her body, running my hands up and down her sides, cupping her round cheeks, and then sliding back up to hold and fondle her dangling tits.

Words were few as we clenched together, our bodies trying to rub against each square inch of the others. My cock was pressed up against her belly, and as we kissed she touched my bare cock with her hand for the very first time, and pushed it down between her legs. We moved our hips in unison, I could feel her wet slit slide back and forth along the top of my shaft.

I sat her down on the edge of the bed and knelt in between her legs. She pulled my head to her tits, rubbing them on my face, then settled back bracing herself with her hands behind her as I began to kiss and lick. I moved my mouth down, working under one big tit; she sensed where I was going and lifted it as I licked along the crease below. Her nipples were ready to explode so I latched onto one and pinched it between my lips before swallowing as much of it as I could get in my mouth. I looked up at her as I began to lick vertical stripes between her tits, wondering if she would recognize were my thoughts lay.

She did and whispered, “Oh Goodness, yes” and pressed my head down her body. I kissed my way down her belly until I was at the stripe of her bush and then pushed back a little in order to lift her legs over my shoulders. I glanced upwards as I began to kiss my way along her silky inner thighs towards her pussy. She was leaning back on her hands while apparently watching in the mirror.

I can still recall the smell of her rose scented bush as my nose first touched it. Her body jerked as my tongue tip brushed her slit, then again as I ran it down to the bottom of the lips. I squashed my tongue flat and rubbed vigorously up and down her pussy. She used her fingers to spread the lips, silently urging me to penetrate. I sucked each lip before moving my attention to her now prominent clit. Taking the tip in my lips I tickled the hood with my tongue, almost getting her off in the process.

“God you are good,” she groaned, “where did you learn that so young?” And then, “Let me taste you now.”

‘Oh damn’ I thought, it had been a while since a woman had sucked my cock and I worried that I would get off too quickly and spoil this perfect morning. But, an opportunity like this did not happen often, and so with shaking hands I held my cock as I stood up and moved it towards her mouth. She soon relieved me of my grip, holding my shaft in one hand and reaching under to tease my balls with the other.

She smiled up at me, “Easy big fella, easy.” She could feel my cock throbbing in her hand. She waited for it to settle as I tried to think of something else, and then she leaned ahead, ran her tongue around the knob, paused again, and then slipped her lips over the knob and down the shaft. She quickly released it when she sensed my knees trembling.

She worked herself back on the bed, as her tits swung from one side of her body to the other. I took a deep breath and remained standing, trying to gain control of my throbbing cock. Her knees came upwards as she spread her legs and reached out for me.

‘I’m okay’, I thought, ‘take it easy now’, as I crawled up between her legs. As my head moved over her pussy, I bent down for a long lick in an effort to get her as close to coming as was I.

She cried out “Jim, please” as she arched her back upwards to press against my mouth, while reaching down to pull me up over top of her. I didn’t want her to touch my cock again, so I quickly moved the knob to her trembling pussy and pressed it home. She thrust upwards to meet me and my cock parted the silky tongues of her tunnel until our pubic bones clashed and rubbed.

I did not last long and probably only managed about 8 or 10 wild thrusts, but she was right with me. The months of foreplay and anticipation for this had pumped our adrenalin levels abnormally high and her body stiffened with my first shot. Her legs clamped behind me, heels digging into my thighs as we found release and relief.

We lay there, still clutched together, her pussy still pulsing around my shrinking cock as she murmured, “Now that was nice, just what I wanted.” And then, “Short but very sweet.”

We laughed, our bodies still glued together as I said, “Give me five and we’ll do it right.” I pulled her on top of me; she lifted her upper body, bracing on her hands each side of my head. Her eyes were already getting heavy with desire and lust.

She swung her tits over my face and said, “Is that a promise? I have dreamed of you joining me in the shower some morning. Shall we make that dream come true?”

I was thinking that this should be a good year. I hoped that I could live through it and graduate successfully. But if I didn’t graduate, there was always next year.

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