older girls younger guys

[lawless_smurf]

Most of the women i've been with have been older than I am, ranging from 5years - 27years older.
I just love older women i guess

 

[SCMOM44]

Not much new to read in here

 

[CamMan22M]

About 6 years ago I met an older woman online. She was in her late 40s and me in my late 20s. She was avg height, short blonde hair, very tan, and nice fake tits. A true milf. We flirtted online briefly and both wanted to meet so I came over to go for a swim one summer afternoon. I met her at the pool and she had a nice brown bikini on sunning herself. I took my shirt off and went swimming quick while she tanned. I came back to lay next to her and start the small talk. All of the sudden she leaned forward and starting tounging me out of the blue. This was awesome so I kiss her back. She was drinking a bit and wanted it. The poor family swimming at the pool left quickly as we kept going at it. Once we finished I hid my erection, which she grabbed through my trunks and she invited me inside......

 

[CamMan22M]

.... When we got inside we started small talking about the beach and ocean as she was from CA and I like to surf. We both started drinking beers and I noticed she stayed in her bikini the whole time only wrapping a small towel around her hips. We both got tipsy and somehow she started taking about her old ex and how he paid for her boob job which explains why she loved showing them off. She asked if I wanted to feel them so of course I did and they were lovely. If I wasnt so nervous I would have made a move right there but I didn't. We talked a bit more and ended on the couch side by side. We moved closer, started touching legs and then touching more. After ten minutes of this we started making out and I undid her top letting her sharing tan lined tits out. She laid down and we got busier. However she never stooped drinking and was starting to feel it by this time. She stopped and laid there and here I am with my cock out on top of this way hot mature woman and she runs out of gas! I try to get her going again and she says its ok and I can just fuck her. She pulls her bottoms down and I waste no time sliding in there enjoying my cherry pie. She is still awake but just kind laying there and I'm going to town. I finally climax after 5 min cause this whole night had been one big cock tease as I pull out and cum on her stomach. She smiled and asked if I was happy. I remember going down on her after as I want her to cum too, shaved bald, but she says not to worry and I end up laying on her naked skin on skin asking myself what just happened. I stayed a bit more as we watched some movie on TV and left as she went too bed.

I wish I had read the signs that she was good to go earlier, but I'm bad at that and my mind was racing thinking of ways not to ruin this. She was very sexy though and knew we were going to screw when she invited me over. I thought I fullfilled a fantasy and was happy. But when I got home I realized I left my board shorts at her place. Id have to go back sometime later to get them

 

[CamMan22M]

Last part

So as I mentioned, I left my board shorts at the MILFs place by accident and called her next weekend to see if I could come by and get them. I came over and we did the awkward small talk thing. I wasnt sure if there was still intrest after last time, but she was drinking again, and had on a skirt and tight cleavege showing top so I liked my chances. However things were going nowhere partially because I was quite nervous again. I figured to cut my losses abd leave after an hour. But she met me at the door and hugged me and there was a huge rush of sexual tension on both sides. We hugged a bit longer and both started running hands over each other then started kissing while standing in the door way. So I decided to just fuck it and asked point blank if she wanted to have sex. Im smooth like that. She thought about it briefly and said "ok" as she grabbed my hand and led my upstairs to her bedroom. She had a nice bed with a large closet with mirrors on the sliding doors and I remember my heart was beating out of my chest. We made out upon entering until she leaned herself over the bed and hiked up her skirt showing a sexy black thong between that mature ass. She spent an hour on her stairmaster every day she always bragged and it showed. I ran my hands and gave over her sweet ass as I pulled out my cock. I was still nervous and had to do some quick stroking to get myself right. I started fingering her wet slit as I rubbed my cock head over her smooth tanned butt watching in the mirror the whole time. Then I grabbed my cock and entered her and she went wild on my cock. I asked her if she liked fucking younger cock which only made her hotter. We had mindblowing sex....... and then I left, lol. She was a little upset with it I think but I remember feeling guilty. I had gotten back with an ex within the last few days and here I was screwing somebody else. That wasnt who I was, but I was so horny I did it anyways. She acted a bit upset and I remember thinking that was that.

Fast forward a month ahead and I got a call from her asking if I wanted to go out and have drinks with a friend of hers and her husband at thier place. They were very nice people I was told and itd be fun. I was still with my ex and told her I had plans already. But it was one of my biggest regrets once I put two and two together. Everytime I had met this lady we always ended up fucking, as and I imagine she wanted me over, I think they were hot tubbing, to swing or just fuck. Ive rubbed a lot out over the years thinking about my sexy mature woman and what would have happened if I came out to meet her friends. I did meet another older woman which was hot, but she was the one I let get away. She just wanted a boy toy to fuck and I dropped the ball. Talk about regrets. Thats probably why I still get so attracted and tirned on by older women today. I know how good they really are.

 

[newplz]

Wow

I've been visiting family for several days by myself. There is an incredibly hot 33 year old friend of the family who has been flirting heavily with me. I've been fantasizing about being with a younger man for quite some time now.

I can't get the thought of going down on him out of my mind. I keep envisioning myself slowly pulling his shirt out of his pants and running my finger along the waist of his pants to tease him. He takes his shirt off as I kneel down and I am looking straight at the hard bulge in front of me. I can't help but place my hand there and hear a slight moan escape his lips. I imagine myself looking up at him as I start to run my tongue along his waistband and undo his zipper. I let out a devious giggle when I realize he has nothing on underneath. Taking my tongue and encircling the head of his cock, I slowly suck the life out of him.

I can't stop thinking about this and all the other dirty things I would love to do to him.

I could read this over and over again.

 

[Kenn89]

Older women/ Younger men stories?

Hey everyone, I've been coming to literotica for a while now, but this is my first time ever exploring and posting on the forums.

I don't know what took me so long!

As a young man of 22, my biggest fantasies have always involved older women. Not that fake milf crap you get in porn, but real, mature looking women.

I'm just curious if any younger men/ older women on this board have stories they'd like to share? I'd love to hear them. I have a couple of my own, but I've never posted anything before.

If someone could help me get comfortable by telling me a story, I'm sure I'd open up ..

 

[Savannah11]

My cougar experience

I've had quite a bit of experience with younger men. There is a 20 yr. age gap between myself and the guy I'm seeing now. Don't have time to post stories in the thread right now, but will come back later. If you want to ask me some specifics, feel free to pm me!

 

[SCMOM44]

Well for those of you who read my post about the kid in the clothes store a few weeks ago, he has been dropping by alot since then, under pretence of visiting my daughter, who is always out with her bf mostly as he well knows,well this warm weather in sunny SC had me out in the yard and getting the pool ready, I was in jeans shorts and a tank top, no bra not looking sexy just scruffy work clothes, well guess who turns up! told him Ash was not here and I was busy, so he asked if he could help, he had already noticed my braless state his line of sight! gave that away, so I asked him to help me get the cover off the pool, this required lots of bending over and he had his eyes glued to my tank top...the iside of t most of the time, I did not really mind as I was getting free labor and I enjoy the attention of young good looking guys anyway.
well we rolled the pool cover back and dragged it to the pool house. He said he was ready to go for a swim, I laughed as the water was nasty,having been covered for months, so I dared him, he loked at the nasty water and laughed saying maybe later, I said I bet it is cold as well as nasty, he laughed saying he liked cold water

 

[SCMOM44]

so again I dared him to go in, he looked nervous and said he had no swim wear, I said he could go in as he was, in his underwear or naked, he laughed nervously and said maybe when its cleaned and a bit warmer, I laughed saying thought you liked cold water, he just smiled
I leaned over to get a water sample and in a way he got a good look into my top,
I could see movement in hs shorts and smiled to myself.
I said I was going to drop the sampe off at the pool store and he could ride with me,stay and vacuum the pool or go home, he opted to ride with me, I went to change leaving him to clean up a few things, I came down in a clean white shirt and clean shorts this time with a bra on
he looked me over and said I ooked nice, I thanked him and we headed out to the store, they tested the water right away and gave me the supplies needed,so we headed back, when we got to the house I again changed back nto my work clothes braless and headed out where Steve had already started on the water applications, he looked up and said I looked nice going out but great in my work clothes, I knew why he said that but pretened not to. as we worked I made sure he saw my boobs a few times and he was practically drooling at the mouth and certainly bulging at the shorts, when finished we were both hot both from work and the situation. I told him he could clean up in the pool house bathroom and said I would get him a towel, I went to the house got a towel and went in the pool house, Steve was naked and under the shower. I stopped dead in my tracks he just looked at me grinning and said I could put the towel by his clothes, I was blushing I coud feel my face burning but still I had to look one lst time at his still errect cock

 

[preacher72]

so again I dared him to go in, he looked nervous and said he had no swim wear, I said he could go in as he was, in his underwear or naked, he laughed nervously and said maybe when its cleaned and a bit warmer, I laughed saying thought you liked cold water, he just smiled
I leaned over to get a water sample and in a way he got a good look into my top,
I could see movement in hs shorts and smiled to myself.
I said I was going to drop the sampe off at the pool store and he could ride with me,stay and vacuum the pool or go home, he opted to ride with me, I went to change leaving him to clean up a few things, I came down in a clean white shirt and clean shorts this time with a bra on
he looked me over and said I ooked nice, I thanked him and we headed out to the store, they tested the water right away and gave me the supplies needed,so we headed back, when we got to the house I again changed back nto my work clothes braless and headed out where Steve had already started on the water applications, he looked up and said I looked nice going out but great in my work clothes, I knew why he said that but pretened not to. as we worked I made sure he saw my boobs a few times and he was practically drooling at the mouth and certainly bulging at the shorts, when finished we were both hot both from work and the situation. I told him he could clean up in the pool house bathroom and said I would get him a towel, I went to the house got a towel and went in the pool house, Steve was naked and under the shower. I stopped dead in my tracks he just looked at me grinning and said I could put the towel by his clothes, I was blushing I coud feel my face burning but still I had to look one lst time at his still errect cock

Wow this sounds soo hot you must have been going wild

 

[SCMOM44]

I turned and walked away wishng I had more nerv...

 

[preacher72]

I turned and walked away wishng I had more nerv...

It canbe very nerve wracking on both ends. Sometimes as much as we want to you never know how the other would react. Ive been in that situation a few times with
Older women. Now theres times that it has worked out but other times i chicken out depending on the woman and or situation but i find the more i turn away makes me want it more and more

 

[shylondoner]

A couple of years ago, I think my mum tried to set me up with one of her friends. She was a beautiful French woman called Cat.

Mum would invite Cat over for dinner and they kept teasing me about needing to find a cougar to show me the ropes. I would get so embarrassed - which make them laugh and do more.

One evening Cat was over for dinner and had too much to drink so she stayed over. I was petrified. I looked my bedroom door when I went to bed. Later there was a knock on the door (I didn't know who it was) so I pretended to be asleep. Whoever it was tried to open the door but couldn't.

I so regret that now. 19 and still a virgin :-(.

 

[sparktj]

I'm a 53yo male and have always loved older women and over the past few years have especially enjoyed sex with women in their 50's and 60's. Last year I met Val, an escort in London who advertised herself as being in her mid-60's. She was lovely, attractive face, fuller figured, gorgeous legs and could have easily passed as early-60's. She was the lady-next-door type, dressed in nice middle-class clothing that any mature lady would wear when going out. Once stripped down to just her sexy lingerie she became very dirty and showed me what a huge appetite she had for sex.

Once I was buried deep inside her and with both of us getting heavily into some intense love-making she whispered in my ear that she had lied about her age and hoped I'd forgive her. I reassured her I'd forgive her anything as I was enjoying fucking her so hard & deep - she sheepishly admitted she had celebrated her 72nd birthday the previous week. I loved it that she taken me into her confidence and I was blown away as she was so sexy and wanton. I held her tight to me, told her it turned me on even more and we proceeded to fuck our brains out.

As we calmed down after both climaxing powerfully, she told me she loved seeing men's reactions when she admitted her true age, and explained that the vast majority of men responded positively though not perhaps quite as enthusiastically as I had. It was so heartening to see her enjoying herself so much and with such abandon. The only difference that I could tell between having her and a younger lady was a slight loss of suppleness. She couldn't maintain the same position for too long without stiffening and getting uncomfortable - but that wasn't a problem as we just enjoyed ourselves in lots of positions!

Having met Val I wouldn't hesitate to see women in their 70's. I've related this experience since to women in 50's and they've drawn much inspiration and reassurance from it.

 

[DrRickMarshall]

I was with a 38 year old back when I was 18, she taught me A LOT!!!!

 

[GyratingGiraffe]

Ah, when I was 21 I dated a hot, adventurous and funny 33 year old woman for a few months. Not a night went by when I didn't have my horizons broadened in some way. Looking back I only wish I'd had more experiences like that and that my horizons were broadened even more.

 

[dagslady]

so again I dared him to go in, he looked nervous and said he had no swim wear, I said he could go in as he was, in his underwear or naked, he laughed nervously and said maybe when its cleaned and a bit warmer, I laughed saying thought you liked cold water, he just smiled
I leaned over to get a water sample and in a way he got a good look into my top,
I could see movement in hs shorts and smiled to myself.
I said I was going to drop the sampe off at the pool store and he could ride with me,stay and vacuum the pool or go home, he opted to ride with me, I went to change leaving him to clean up a few things, I came down in a clean white shirt and clean shorts this time with a bra on
he looked me over and said I ooked nice, I thanked him and we headed out to the store, they tested the water right away and gave me the supplies needed,so we headed back, when we got to the house I again changed back nto my work clothes braless and headed out where Steve had already started on the water applications, he looked up and said I looked nice going out but great in my work clothes, I knew why he said that but pretened not to. as we worked I made sure he saw my boobs a few times and he was practically drooling at the mouth and certainly bulging at the shorts, when finished we were both hot both from work and the situation. I told him he could clean up in the pool house bathroom and said I would get him a towel, I went to the house got a towel and went in the pool house, Steve was naked and under the shower. I stopped dead in my tracks he just looked at me grinning and said I could put the towel by his clothes, I was blushing I coud feel my face burning but still I had to look one lst time at his still errect cock

If his cock was hard and he smiled at you as you looked, he wants you as bad as you want him. Sounds so erotic....tease him a bit more and then let him have what you both want so bad. Keep us posted pretty lady!

 

[wolex]

older black women

I love to date a black woman in in mid forty

 

[bigdeal7]

AMAzing!

this just made my day! 20/m and the idea of an older woman is one idea that i would love to explore more. bravo!

 

[SCMOM44]

Not much new to read in here lately

 

[Pj2424143]

Not much new to read in here lately

I know.... I have been on and off all day,, seems so quiet everywhere I look

 

[eric60red]

I have a problem finding older girls than me

 

[SCMOM44]

I have a problem finding older girls than me

have you tried the morgue...lol sorry eric

 

[Pj2424143]

have you tried the morgue...lol sorry eric

I was going to say the same thing