Her Son's Best Friend

From the Author: I didn't know which category to put this part in. This story part has anal, mature, group sex, bisexuality (or some may call it lesbian) and finally, just a bit of incest. If any of those may offend, you have been warned.

This story is told through the eyes of a woman, Barbara Bradley, 42-years old, married for the second time. Her husband is Terry and she has two children, a son and a daughter from her first marriage. She has begun a MILF relationship with two of her son's best friends.

I woke late on the Monday morning after my son Adam's pool party for 9 of his friends. My husband Terry had already left for work so I lay there in my bed, reflecting on how my quiet suburban life had changed in the past two weeks.

Terry is my second husband and we have been married 5 years. I am not at all unhappy with him, either as a loving companion and new father to my almost adult kids, or as the competent lover that he is. So how did I get into this ticklish situation where I now respond – no, not just respond – I sexually crave two of Adam's friends, Kurt and Jeremy.

Admittedly, the two of them knowingly set out to come to my home to seduce me, well aware that Terry and Adam were not there. But I could have said no, how did I allow myself to be seduced in this way, by two young men, 20 and 22, a generation younger than me? I searched for a fault in my marriage that might have prompted me to take these two young men into my body.

The only thing that fateful day was that I had dressed very sexy and gone to my husband's office with a view of seducing him, but he rejected me out of hand, sent me away because he was too busy. So the boys got me on the rebound, as it were, and they took full advantage of my momentary weakness. But that was then, and this was now, two weeks later, and yesterday (Sunday), I had behaved like an out-of-control slut.

I had gone in to our guestroom and allowed the young woman Georgia to lay her head in my lap while her new boyfriend Jeremy – he of the large penis – had fucked her. Then, standing in my kitchen, I had allowed the surly, arrogant Kurt to finger me to an orgasm while the head of his penis was wedged tightly up against my anal ring. Finally, I had knelt down on the floor and given Kurt a blow job, even while my son talked to him through the open window above. My God, what depravity had I sunk to? Now that I had pretty much dismissed the hunch that Terry may have been having an affair with his PA, why did I still need to behave like this?

It was also amazing good luck that Terry had not sprung me in bed with young Kurt, which is where I had so wanted to be, and would have been, but for good timing when my husband came home early.

Yes, I did seem to be out of control. Yet, as I lay here in my bed, the other side still warm from my husband having slept there, my fingers trailed over my breasts and slid in among the lips of my pubis. And my mind roamed over how I could arrange another session in this very bed with Kurt and possibly Jeremy – the latter depending on how monogamous his new relationship with Georgia was.

Would I appear too eager if today I called up Kurt and invited him over one day this week when I was home alone? But I realised that I didn't even have his number, so would I have to roam around in my car to the usual haunts that Adam and his friends frequented, hoping to find Kurt without Adam nearby? No, that would not be a good look and would signal desperation to Kurt and Jeremy. No, I had to retain a degree of dignity about all this and at least wait for one of them to make the next move. I had confidence that they would, given the pleasure that they had both derived from my mature body.

It was hard getting through this week. I jumped up every time the phone rang, but they never called. I was very cautious about what I said around my son, not wanting to arouse any suspicion. After all, I was unsure how discreet this pair would be. How good was their relationship with their buddy Adam? Were they likely to try to gloat over their sexual conquest of his mother? But I saw no sign that Adam had any suspicion about me.

On Friday afternoon, as I reflected on the lost week just gone, and contemplated that nothing could happen on the weekend due to Terry and Adam being around most of the time, I got a call.

"Hi Mrs Bradley," it was Kurt - he who didn't say much, just let his penis do the communicating, at least around me. That was it, then silence, waiting for me to acknowledge him.

I have to admit that I subconsciously adjusted my voice, attempting to sound sexy and sultry. What was it about this young man that brought out all the wrong things in me. "Hello Kurt, I was hoping you'd call. I mean, I don't have your number."

"That's okay, you don't really need it. I will call you when I want you."

How dare he, how super confident, treating me in this cavalier way. I wanted to slam the phone down in his ear, swear at him, tell him to get lost, using the language that he would truly understand, words I would not normally use. Yet, hearing his voice in my ear, I felt a twinge down there, right around my vagina and clitoris. Without even being touched, I felt an arousal. Was it simply from hearing his voice? I reached a hand down and, through my skirt, pressed against my pubis before answering him, "So what do you want? What can I do for you?"

"Oh Mrs Bradley, you can do a lot for me. I never knew an older woman could be so hot."

"Not too much of this older woman nonsense," I retaliated defiantly, "I'm only 42, I can keep up with the likes of you, young man."

"Yeah, well that's what I wanted to talk to you about. Your husband fucked us up by coming home early last Sunday, just when I was ready to have your arse."

I drew a deep breath at the suggestion of anal sex with young Kurt. It was not that I wasn't experienced at that type of sex, but it had been over 7 years. My first husband had a leaning toward it, and I had indulged him because I loved him then, despite his philandering. Now my hand, that had been pressed against my pubis while listening to Kurt talk, slipped around to my back and down inside the waistband of my skirt. The fingers on the outside of my panties pushed the silky material in between my arse cheeks, putting pressure there against my anal ring.

"Kurt, we were damn lucky that he didn't catch us in bed together, another minute and he would have. I doubt that I would have been talking to you now, and my married life would be in tatters."

"Yeah, well shit happens, but it didn't this time. Sure, we were lucky, but let's not dwell on that. So what about it, would you like to have Kurt's cock up your arse?"

He was just too cocky for his own good, I needed to try to bring him down a peg or two, I tried disinterested nonchalance. "I don't think so, Kurt, I don't want to do it that way ... if you really want me, we could do it the normal way again sometime," I offered, not wanting to totally discourage him. "Even standing up against the wall again," I added, "that was quite exciting, I had never done it like that before."

"I suspect there's a lot you haven't done, and that's why Kurt's here to teach you, Mrs Bradley. So when can I come and see you again?"

I didn't want to sound too eager, "Err, let me think. Well, the weekend's out, of course."

"Does it have to be?" he interrupted.

"Yes it does, Terry and Adam will be around most of the weekend. I don't want to take any more chances of being caught. It will have to be a weekday when I can lay in bed with you and we can have the time to do different things..."

"Like my fucking you in the arse," he persisted.

"Oh, I don't know about that, Kurt, we'll have to see about that," I teased, my finger had slipped inside the back of my panties. It was now tracing the soft smooth skin on the inner cheeks of my arse, thinking about Kurt having his hard penis there, just like he did in my kitchen last Sunday while he fingered me.

"So how's Monday then, Mrs Bradley?"

"Yes, I'd say Monday could be very good, Kurt," I told him, trying to sound calm while silently stressing that I would have to wait 3 days to feel him inside me once more. "What about you come over early? My husband leaves for work about eight. If you wanted to park just down the street, you could come in as soon as you see him leave. But don't park your car on my driveway ... you know, the neighbours and all. When he goes, I will leave the back door unlocked. I will still be in bed, so you just go around the back of the house and let yourself in. You know where to find me, I'll be ready for you."

My God, how devious I had become, planning it all so meticulously.

"Sounds good to me," he told me, "see you Monday." A click and the line went dead.

Over the weekend, I must have been unbearable to my family. I found myself snapping at them over the most ridiculous things. I should have been happy, on a high because I would have Kurt once more on Monday. But instead, I seemed to be blaming them and their being around the house for my not being able to have him sooner.

At last, Monday morning arrived. I hadn't slept a lot through the night, I kept thinking about having Kurt come to visit me. Would it be different not having Jeremy there too? Could I bring myself to do all the things that Kurt may demand of my body? Obviously, I thought about his obsession with anal sex. When it actually came to his being here in bed with me, could I bring myself to do it, could I roll over on my stomach and bare my arse – my parted cheeks – to him, to let him have his way in there? It had been so many years since I had felt that experience with my first husband.

6.30am ... 7 ... 7.30 ... I had lain there silently, at last hearing my husband rise, go in to have a shower, then out to the kitchen where I was thinking of him having his morning coffee and some toast – his usual ritual. I had fortunately been to the toilet last night - vacated my bowels, I think the medical people call it. I mean just in case something happened back there. Then I had enjoyed a deep warm soaking bath. I came to bed late, letting Terry get to sleep. I had hoped that he wouldn't wake up horny and want me this morning. I would have had to shower to make myself fresh again.

The bedside clock showed 7.50 and I heard Terry enter the bedroom, come up to my side of the bed. I pretended to be asleep when he leant over me and kissed my cheek. I felt guilty as he did that, knowing that even before he reached his office, I would probably have Kurt's penis up inside me.

I kept my eyes shut tightly until I heard the click of the front door closing. I jumped out of bed, shedding my long negligee and going to the chest of drawers, taking out a sexy baby doll short nightie, not bothering with the matching panties. I grabbed the tube of KY from under my fresh supply of underwear. I dropped the KY on the bedside table and hurried out to peep through the front window. I saw Terry in his car pulling out of our driveway. I looked up and down the street, couldn't see any sign of Kurt or his car. Was he late? If he wasn't there to see Terry go, how would he know what time to come in?

'Oh, don't mess up this day, Kurt,'

I thought as I hurried through the house and unlocked the backdoor, in the kitchen. I stood for a moment recalling the events of the pool party a week ago, the events that took place over by that window.

Then I scurried back to my bedroom, over to my bed. I straightened out the sheets, threw back the doona so that I would be lying with only a sheet covering me. I lay there on my back to wait, I found myself nervous. The first time it happened, there was no planning, it was all impulsive and at the guys' bidding. This time, I was the instigator.

The minutes ticked by, the house was silent, and my nerves increased.

'Oh please, come soon,'

I silently pleaded. I slipped my fingers down to my pubis, found that I was already wet there, just from my eager anticipation.

My mind raced, I had very carnal thoughts. On an impulse, I rolled over to one side, I reached out and grasped the KY tube, lathered some on my fingers and slipped them back around to my arse. I pulled my legs up under me to part the cheeks and my fingers slipped in to my anal ring and I spread the sex gel all around, even daring to slip two fingers inside my anus to make it slippery deep in there.

The preparation completed, I grabbed a pillow and placed it midway down the bed, then I rolled over onto it so that my tummy was lying on the pillow. It had the effect of raising my arse up higher than the rest of my body. I reached my hand back and placed the KY tube to balance on one arse cheek. Then I settled my head onto the remaining pillow and continued to wait impatiently.

Moments later, I thought I heard a sound, was that the back door clicking closed? My head on the pillow was turned away from the bedroom door. I wondered if I should turn my head to be able to see Kurt come in to my bedroom. I heard another sound, was that someone entering my bedroom? For a horrible, terrifying few seconds, a frightening thought hit me. What if Terry forgot something and came back to the house to find his loving wife lying face down on the bed, her bare arse raised in the air, and lube liberally spread between the cheeks?

I heard more sounds, closer. I was now certain that there was someone in the room. I assumed, and hoped, that it was Kurt. But he hadn't said a thing about finding me this way, the suggestion implied by the way in which I lay – the KY tube prominent on one bare cheek - that he would get his wish and take me in the arse. Then again, I had already found him to be a young man of few words.

This was nerve wracking, I heard what I thought to be the sound of clothes being removed. I definitely heard shoes falling on the floor, the sound of a belt buckle. I wanted to turn my head to the other side and look, to again see this virile young man, who was about to take me where I hadn't been taken in years.

I felt the bed move, from the weight of someone on the side of it, either sitting there or maybe placing one knee while he faced my half naked body. What was he doing? What was he thinking right now? Was he excited to see me this way? He might be taking in the sight of my raised arse cheeks, with the gel glistening in the darker recesses between them, and the tube of KY for him to use left perched precariously on the smooth top of one cheek.

I jumped at the first touch of his fingers grazing my smooth soft arse cheek, lifting off the tube of KY. I guessed that he would be very happy at this moment, that he would be squeezing the KY onto his fingers and coating his penis with the gel. His penis would have to be hard by now, seeing the tiny target of my proffered puckered anal ring nestled deep between the cheeks of my arse.

Since Kurt wouldn't acknowledge me or say a word, I broke the silence, "Good morning young man ... so, are you surprised?"

"Very!" was Kurt's curt reply.

"Is this what you want?"

"Yes!" was his husky voiced reply from somewhere just above and behind me. "I didn't think you would let me do it."

"You seemed very insistent."

"Have you ever done it before?" he asked me.

"Yes, my first husband liked to do it."

"Did you enjoy it?"

"Oh yeah, it was alright," I told him, "not as good as putting it in the right place. How about you, Kurt, how many women or girls have you done this way?" I was curious.

His voice seemed to catch on his saliva, or was it dry mouth instead, "None, you're gonna be my first."

I was surprised to hear his admission, even more surprised that he would reveal that to me. He had seemed so keen that I figured he was experienced at anal sex. Now I was hearing the normally arrogant, cocky young man sounding just a bit unsure of himself, hesitant even. I wished that I could see his face. "Do you still want to do it then, or will I roll over and you can have me the usual way?"

"No, it's okay!"

"We could still try it later," I suggested as a compromise.

"No ... no, it's now, I want to do this now."

"Do you want some help?"

"No, I've read stuff, seen porno stuff, I know what I'm doing." The usual gruff and moody young Kurt was back, regaining his confidence.

I felt him grasp my hips with both hands and my lower torso was hauled up, forcing me onto my hands and knees. I felt something hard pushing between the cheeks of my arse, it was obviously the head of his penis. Then it was sliding around the well-lubed inner surfaces of my cheeks, dipping into the cleavage until the rounded tip suddenly caught on my tiny puckered ring.

"Ohh!" I heard Kurt gasp as the head of his penis was captured by my anal entrance.

With his lack of experience, I was apprehensive that he would try to come in too fast. "Easy Kurt," I urged, "not too quick, I don't want you to hurt me. It can feel good for both of us, but you've got to go slow."

"Yeah, okay ... okay!" were his dismissive words, rejecting my advice. I felt pressure back there, he was pushing his penis, trying to make it fit in through my tiny opening. His penis slipped on the coating of gel and it speared upward within my arse cleavage. "Damn it," he muttered, obviously frustrated at it not immediately going in the way he wanted.

"You'll need to hold your penis steady with one hand and just push gently until you feel my sphincter giving way," I advised.

"Yeah, okay, just let me do it, alright," he was getting testy, probably embarrassed at his lack of experience.

I held my breath, determined not to say anything more, if I could help myself. I felt him pressing inward again with his hard erection. He must have taken my advice and be holding his shaft steady because it didn't slip this time. I tried to relax in spite of the firm pressure coming at my arse and then I felt the sphincter give way, opening up to let the knob of his penis into my anal passage.

Ooh, I felt very full, I had forgotten this incredible feeling of fullness in my rectum as the penis begins to occupy all the available space. I heard him gasp loudly, sounding like he was enjoying the tight sensations on his penis as it was gripped tightly by the inside of my arse.

Then he was pushing some more, I could feel his penis shaft making ground inside my rectum, going ahead an inch at a time. It had been so long since I had experienced anal sex. My memory of it was a mixture of good and not quite so good. He kept pushing and I felt some discomfort – not really pain. Then when it felt like I couldn't get any more of his solid penis shaft inside me, he stopped. I could feel his thighs and his tummy up against me and knew that he had seated his penis all the way home inside my rectum.

"How does it feel in there?" I dared to ask him.

"Oh God, it's great!" he enthused, unusual for a young man not keen to show his emotions. "Oh, feels like I want to cum, but I can't yet. I want to enjoy this a bit longer."

"You're okay, just do what feels good for you," I encouraged in a motherly manner to the young man 20 years younger than I. "If you have to cum, just do it, let it go."

Well, he did ... do what feels good, I mean. He began withdrawing until only his penis head remained inside my anus, then he plunged it all the way back into my rectum. Again and again he thrust, his loud grunts telling me how good it felt for him as his thrusts picked up speed.

I had no pressure on my clitoris this way and I knew I wouldn't cum. Still, I was enjoying giving this young man something he had wanted, but had never experienced previously. I stiffened my arms to hold my body upright as the thrusts of his penis in my arse grew harder and faster, threatening to flatten me on the bed. I could hear how close he was getting from his gasping breaths and loud moans of pleasure.