Mother In Laws First Anal Experience

First time, well worth the wait!

This "mother- in- law Fantasy" ex mother in law actually is more an ex son- in -law story and differs from most you'll read in two ways. First, it's coming from the Mother- in- Law, second, it's actually true. 

First, quick background. I was a fairly young mom and my ex son- in- law was a few years older than my daughter so the age difference is only 15 years, I am now 58 he is 43. She left him for another and nothing other than some flirting ever happened when they were together.

I always thought he was attractive and in great shape. From day one something was there but again, not going to happen. I had remarried an older man and sex was few and far between so yes the thoughts were there. When alone we would talk/borderline flirt. For example, on occasion I would "accidentally" walk into a room still buttoning my blouse, bend over at just the right time etc and would catch him look and give a smile. It's all I had. Once he needed to give me a ride somewhere and he showed up with a huge hard on set a top his thigh in tight jeans, very obvious, very intentional. Anyway, recent times are what your waiting for.

My daughter left him, but we stayed close as grandchildren are involved and we live close by. My husband and I have not had sex for many years, all he wants is companionship but I need more. As neighbors my ex son in law stops by to say hi or borrow tools at times. We have talked, really he is my only confidant. He once commented how good I looked and what a lucky guy my husband is and I laughed and explained his lack of interest. His answer was what a fool he is and that if he had me he would start and end each day on top of me. Definitely the most obvious of all our flirtations. At least to that point. 

More recently when discussing the subject he said I needed a "friend with benefits" and that many guys would volunteer for the job. I said yeah more old guys like my hubby and he said no shot, told me I was bound to be more than just his older women fantasy. As he got off the couch I saw in his shorts that same hard on from that day years ago. I was about to explode.

I felt he was about to give up as he was doing all the work and I was not doing my share. I was scared. We both wanted it and trust each other completely but I was scared. He basically let me know where and when to be but I was scared. I posted for advise to a different site and although many responses were nasty, calling me names, telling me I was hell bound, that I was to be nothing more than a toy to him, most telling me as my one other friend/confidant had that I better prepare for my first anal experience, etc.. Some actually understood and where in similar binds, some offered great advice, I finally I took some.

I still could not go to him, scared. What I did was call and ask if he could stop by to remove a limb from my roof. Actually a twig I tossed there. He said he could come at a time that afternoon, when he knew my husband was at work. I "forgot" he was coming and was only in my robe when he showed. He took all of 2 minutes and removed the limb/twig. When he came in I said, and this was actually my own line, "thanks for coming and doing that for me otherwise I may have had to wait for a slight breeze to do so." He said he's glad I didn't wait because he had waited long enough to do this. He leaned into me and kissed me softly as he slid his hand beneath my robe and across my chest. I felt a wave of panic and my heart felt like it was pounding out of my chest. I was frozen.

He stepped back a bit and removed my robe. He grabbed me by the hand and backed into my couch where he sat down and undid his pants. I went to my knees and removed his penis from his pants. It was beautiful, exactly how I imagined. I gently kissed and licked it then took it in, I cannot remember the last time I had a cock in my mouth. He sunk into the seat and told me he always knew I'd be awesome at this. Then he told me he dreamed of coming in my mouth but that that would have to wait for another day as he had other plans for me.

He got up and laid me on the couch, removed his shirt, god he looked so good. He then assumed my prior position and began licking me. I have never felt anything that good and honestly thought he was going to make me come with his mouth. He got up and slid me up a bit, my back resting against the arm of the couch and he climbed up and slid his cock between my breasts. He then climbed higher and stuck it completely in my mouth, slowly in and out I fought the urge to choke as I did not want to let him down in any way. 

He then lowered himself and again kissed me softly. He began rubbing the head of his cock on my clit, teasing me, I was dying! Then very slowly he went in, all the way in. He looked me in the eyes and said "finally". He fucked me better than I had ever been my entire life. I came for the first time in so long and it was amazing. He continued fucking me and I was surprised he hadn't come. I briefly thought maybe I wasn't doing it for him. Then he gave me a really good long kiss and slid out of me.

He turned me over and slid me up and over the arm of the couch. O god look at that ass he said and then he rubbed and began kissing it. He kissed me right on the anus and then asked if I had ever been fucked in that sweet ass before? I said no, that I didn't do that. he laughed and said "you do today honey"! I was nervous but no shot I was to stop him. He did, thankfully, bring a pack of lube. He put some on my butt and some on his penis and lined up. I was very nervous and then felt the head of his cock press against may rectum. God it hurt going in. He was slow and gentle but it still hurt even with the lube. Slowly he started going in and out, then faster, then he came out because he wanted to see it go in again, ouch, he then began going a bit less easy on me and faster. He grabbed me by the hair and turned my head slightly towards him. He kissed me and asked how his cock felt in my ass. I told him it felt great, that I loved feeling his cock in my ass, said he loved hearing that and then he exploded in me, he kept sliding in and out of my ass and finally pulled out and turned me over.

We rested a bit and talked some. I asked if he thought I was a whore. He said, "why, just because your a married woman who just had her ex son- in- law's cock in her ass?" He laughed and said, "yeah but it's fine so long as your my whore."

That afternoon was the best sex of my life. I have no regrets. We have repeated a couple times now and it just gets better. I know it will end soon but again, no regrets. My husband and I actually get along better now as a result. I was getting bitter and so all we did was argue. Now he has his companion, I start most weeks getting fucked by a hot younger guy, and we get along great. My whole life I did for others, finally doing for me!

Sex with boyfriend as his father watches

Worlds hottest story

Started working at a hardware store a couple of months ago. I only assist at the cash register but occasionally my boss, Mr. Chang tries to teach me a few things by making me help with inventory. My step-dad told me to get a job as a way to keep me out of trouble. I'm going to start college soon and my step-dad thinks I've been spending too much time at home. You could say that I've gotten a bit boy crazy in the last couple of years and my friend Janet and I have become partners in crime. Nothing illegal, but things have gotten naughty to say the least. My step-dad doesn't approve of my current boyfriend. He says he's too old for me. I don't think ten years is all that. At least he says he's 28, but I suspected that he might be older.

Anyway, it had been a slow day and Mr. Chang had me in the back room doing the inventory thing. His brother-in-law and work partner, Mr. Kwan had taken off early and Mr Chang was busy dealing with costumers out front. My boyfriend had arrived and he sneaked into the back to surprise me. He just happens to be Mr Chang's son. He startled me, but I was happy to see him. He seemed awfully lustful, taking me into his arms and kissing me passionately. I didn't reject all this wonderful attention but I did keep in mind that Mr. Chang had a closed circuit monitor covering the area we were in. As David held me, I could tell he was hard and excited. I told him that Mr. Chang could walk in at any moment. He just smiled and said that it just make it all that more exciting. I figured that in order for Mr. Chang to watch us on camera, he would have to actually come into the back area. With costumers coming in and out of the store, the chance that Mr. Chang with come back here was a bit smaller.

David grabbed my elbows and pulled me downward. I knew what he wanted and the naughty girl in me decided to play along. I playfully pulled his zipper down, as he unbuckled. Knowing his dad was just in the other room, made it all so naughty. I loved to run my tongue under his cock before swallowing it pressing my lips around and over it. Just as I was getting into it, he pulled me up and began to pull my clothes off. I love it when he does this, and it gets me really hot. I felt so vulnerable being naked in such a place, and my worries about his dad surprising us had me more worried.

I held my arms around my breast, and felt my nipples harden more against the cool air in the room. Kissing me on the neck and nibbling on my ear, he whispered that he loved to look at me. He then surprised me by asking if I liked older guys. I told him I was dating him, so yes, I was. He then asked if I would fuck any of his friends. It was my time to surprise him. I said that I would even fuck his dad if he showed any interest in me. That shut him up, but he continued kissing me and leaned over to suck on my nipples.

"Ohhh, yes. yes," I moaned to encourage him to continue.

"You want me to get my uncle in here too?" He asked finally, probably to test if I was serious or not.

"Yes, I like that, yes, very much," I didn't care exactly what he was saying, but wanted him to continue sucking my tits. Since Mr. Kwan had left early, I must have decided to ignore his comments about him. My hunger for David's cock was growing.

Having pulled his pants down, David pulled me up into the air. My legs wrapped around him with his cock poking me underneath. "My dad and uncle think your hot. Why do you think they hired you."

Getting irritated by his lack of focus, I told him, "Look, Mr. Chang. I want you to fuck me right now." After all, David's last name was Mr. Chang too, right?

Placing me back onto a nearby table, David started fucking me. I didn't know it at the time, but the older Mr. Chang was listening to us from the door. As I moaned for more, he thought that I was thinking of him.

"Harder, yes..." My legs found themselves stick up into the air, resting on his shoulders. David grunted as he drove his cock deep into me. I no longer thought about where we were or that we were on camera. Having forgotten that, I was hot and burning in the moment. Cumming all too soon for my taste, David came deep inside me.

Mr Chang and his brother-in-law would later watch the surveillance video tape of the whole thing.

(And What happened next day*******)

But that didn't happen to the next day...

First Time Sex With Older Women

Women will like this TRUE story more than guys) I met my older brother and several of his friends at a bar to say goodbye one evening shortly before I was shipping off to boot camp. I was leaving in four days and wouldn't be seeing him again. I was only 18 but had a fake ID as most of us did in those days when the drinking ages were all on the rise. My friend David was with me; he and I planned to just bum around together for the next few days.

I ended up sitting between my brother and his friend Brenda. She was a pleasant, good-looking, voluptuous brunette whom I had met numerous times before. We had a few beers and just chatted and laughed about things. David and I both thoroughly enjoyed being accepted by an older crowd and being included by my brother.

After a few hours of this, it was time to go while we could still function. I had earlier mentioned that I was staying in a hotel for my last few days in town. As I stood up and was telling Brenda that I had enjoyed her company, she looked me coolly in the eye and said, "Would you like to take me to your hotel room?"

I must have looked like an idiot for a moment, staring blankly back at her as I digested what she was asking me. I was trying to figure out if I had heard her correctly, if she was asking what I thought she was asking. I had always enjoyed looking at Brenda's body, her generous breasts and her curvy ass, but had never thought about her in a sexual way because it had never occurred to me that a mature woman like her would be interested in me. She was a professional career woman who had just turned thirty and owned her own home. She had been married and divorced and lived a real life and here I was, a mere pup of eighteen years. I had never had much luck with girls my own age and here I was being invited to have sex with a real woman. It seemed to take forever for me to go through the mental gymnastics, but I doubt more than two seconds elapsed. I had no doubt that I wanted to be with her, but I did doubt that she was really asking me to.

"Sure, " I finally responded. She grinned at me and I knew then that I understood correctly. The look in her eyes told me that I was really in for something. She took my arm in hers--giving me an erection that would cut wood--and brought me to stand by my brother. "I'm taking your little brother off to have my way with him" she said with a laugh.

That was the first time I ever remember seeing my brother speechless. After he finally picked his jaw off the floor he simply said, "Have fun. Make sure he gets to the Navy on time."

I had almost forgotten my friend David in my excitement. Brenda and I went over to him and I said, "Uh....hey...something's come up." He looked back and forth between us, at two people grinning in anticipation and oozing sex. He was obviously going through some of the same thoughts that I had just moments earlier.

"Uh, Dave....I'm really sorry, but I'm going to go with Brenda here. I hope you don't mind. Why don't you just stay here with these guys?" I felt a little bad about it, but this was certainly well within the "guy code". Besides, I couldn't count the number of times that David had blown me off to go be with his steady girlfriend. At any rate, there was no way in hell I was going to miss out on this opportunity. He took it good-naturedly and we were out of there.

As we walked outside, Brenda put her hand brazenly on my ass, squeezing my cheek and telling me she couldn't wait to get me naked. You can imagine the effect all this was having on a young, fairly innocent, fairly inexperienced guy. I was having a hard time maintaining my composure and thinking clearly in my excitement.

Fortunately, my hotel room was close and we made it inside quickly and without being accosted by the police for indecency. We threw our arms around each other and kissed hotly for some time, standing just beside the bed. I was lost. I had never been kissed so passionately or so thoroughly by the few young girls I'd been with. I got into it and returned as best I could, reveling in the sensations going through my body.

She was frantic to get my clothes off, pulling my shirt over my head and tearing at my jeans. Between the two of us, we managed to get each other naked very quickly. I had been looking forward to this and greedily put my hands on her luscious breasts. They were very generous and nicely shaped, with small pink circles and long, firm nipples. I had never touched such mature, wonderful breasts in my short life. I leaned toward her and took her nipples alternately in my mouth. She responded by moving her groin against mine and grinding into my rigid cock. I moved my hands to her curvy ass and pulled her hard against me, stroking my cock against her.

This was enough foreplay for both of us. She moved backwards to the bed, pulling me onto her as she lay on it and both of us moved towards its center. We kissed and groped each other for a moment until she said, "I want you inside me now."

"Brenda, I'm afraid I'm going to cum too fast. I'm so turned on I could easily cum right now, and I'm not even inside you."

She responded with a smile, "Don't worry sweetie, I want you to cum in me no matter how quickly. I know you'll be ready again soon and I plan on using your body all night."

I was sold. She was wet. I was inside her seconds later. She felt fabulous. Her body embraced and welcomed me, in sharp counterpoint to the feelings I'd had with the few previous girls I had penetrated--almost as if they had been fighting my cock on its way in. Brenda was so wet and ready for me, eagerly pulling me toward her. I held her in my arms close to me and still for a moment, enjoying the feeling and wanting to record it for later, hoping that I wouldn't spill my seed in the next few seconds.


I calmed myself and kissed her for a few minutes, staying deep inside her and touching her. I was mesmerized by the sensations of being inside this lovely woman.

To my surprise, I didn't immediately shoot off and embarrass myself. This sensation was so different from my previous frantic experiences that I was able to enjoy it for an amount of time that surprised me. Brenda kept up a stream of talk, constantly encouraging and directing me. She pulled her legs up close to her chest, aiming the head of my cock at her g-spot (I was oblivious of its existence and purpose at the time, but she was clearly not). She had apparently been just as aroused as I was--within moments she was moaning sharply and moving toward a quick, sharp orgasm. As I stroked in and out of her and she cried out, I joined her, releasing myself into her. This pushed her further and we rocked back and forth against each other eagerly.

She released her legs and wrapped her arms back around me and we began kissing again. After a moment, she began grinding against me, and then suddenly opened her eyes wide in surprise. "My God! You are still hard!"

"I am? Are you sure I'm not just hard again already?" I asked, being ignorant of my own bodily response.

"You didn't lose it at all. Get busy and start moving again, I want you to cum again."

I was so aroused and enthralled by this mature and sexy woman that I'd have done anything she suggested, anything at all. I found it hard to believe that I had maintained an erection through that orgasm, but I wasn't going to question it. I worked hard against her body again, and again she pulled her legs back so I'd hit her g-spot. She came again soon after, her face grimacing and her hair shaking as she cried out unintelligible words, mostly "Uhhhhhhh!"

"Let me be on top of you, " she said, rolling us both over. I laid back and watched her ride me, loving the feeling and the view I had never experienced before. It was easy for me to hold off this time, enthralled by the experience more than the physical sensation. Sweat broke out on her entire body as well as mine. I watched her cum yet again, her hair flying and her round breasts shaking. I kept my hands on her ass throughout, squeezing her cheeks and enjoying her movements.

She fell on top of me to rest for a moment and to give me more passionate, appreciative kisses. I loved touching her soft skin and caressing her back and ass.

I had built up some confidence by this time since she hadn't thrown me out of bed or stormed off in disgust, so I rolled her off of me and told her to get to her knees. I moved behind her and entered her as I took her breasts in my hands. I began to ride her vigorously, my hips slamming into her sexy ass as my cock slid in and out of her. I loved watching her back and her ass moving; this turned me on to no end--ever since, this has been my favorite view of any woman's body. I came again, violently. She screamed as I did, which I took as a good sign, and then we lay down on the bed holding each other.

I can't recall exactly how many times we coupled again that night; it was twenty-two long years ago, the entire span of my very full Navy career. I do know that we got out of bed and stood up to have sex at least once and that she rode me several times and I rode her from behind several times. I am sure that I came more that night than almost every other night of my life. I'd like to think that she did as well.

I woke up in bed with a naked woman for the first time ever and kissed her awake. She rolled me on my back and said good morning to my cock with her lips, then climbed on top and rode me for another orgasm for both of us. This time I could see her in the morning light and thoroughly enjoy the sight of her breasts moving above me and the expression on her face when she came.

While she made coffee we discovered that we were both starving, so she suggested that we shower and get something to eat. At this point, I was surprised that she was still around and hadn't gone off to do whatever it was that adult women do during the day. Little did I know that I was in for another shocker. "Why don't you check out of your room and come spend the next few days at my house?" she asked with an impish grin.

"I can't imagine anything I'd rather do than spend these last few days with you."

We showered together and I soaped her sexy body all over, concentrating on her fabulous breasts and then her generous, shapely ass. I took her from behind while I soaped her front, making her cry out loud again as she came. These days were full of brand new experiences for me, including this one--showering with a sexy woman and entering her without stopping to ask if it would be okay.

Once we got to her house, we headed straight for the waterbed that I had sold her a few weeks earlier when I gave up my apartment. She asked me to taste her and taught me how to do it well and how to make her cum reliably. When she showed me how hard she could cum from that and how much she enjoyed it, I became a convert to the cult of cunnilingus. I was amazed at the power this gave me over her body and how affectionate she felt towards me afterwards. To this day, I love going down on a woman who enjoys it more than almost anything.

We spent the next three days together, most of it in bed. She did let me sleep in the next day while she went in to work briefly and arranged things for days off, but for the most part the real world did not intrude. We watched some movies and had some food delivered, but mostly just lay around naked together either in the afterglow of sex or working each other up towards more.

I became addicted to going down on her and making her cum hard, and then entering her to do it again. I got spoiled being with such an orgasmic woman so early in my sex life. She sent me a very nice letter in boot camp, but by the time I ever visited my hometown again she had settled down seriously with another man and I stayed away. I remember thinking what a lucky guy he was to be with such a sexy woman.

Brenda was my first in so many ways: --My first older woman --the first woman I 'shacked up' with --the first woman I slept all night with --the first woman to ever wake me up with her mouth on my cock --the first woman to ever 'pick me up' --the first woman I ever gave an orgasm to through oral sex --the first woman I ever made scream during sex --the first woman I ever saw get sweaty from sex --the first time I had sex in a hotel --the first time I had a woman on top during sex --the first time I had sex in the shower --the first time I had sex standing up

I will never forget her. I will always be grateful. Boot camp was so much more tolerable after those days with her, but I was never happy with young girls again--even now I prefer a more mature woman to a younger one. Fortunately, I did experience a few other older women after that who also taught me a few tricks.