Taking heed from SEAJ, I am starting this thread for all bros out there to share experiences with older more experienced women when we were younger. I am very sure some of us learnt the finer art of sexual enjoyments whether to receive or to give from some MILF that we may have encountered in the course of our lives... I am attaching the experienced I had to start and hope all you bros out there will share your experiences as well!


I had a fling once with an older women when I just started working in my early 20s (I was 22 then)...it was good but thinking back, I actually think I wasted that opportunity for not fully utilizing the chances and every moment that I could've shagged her!

She was a Manager in the sister company where I worked as a Junior Buyer then. I was actually in a different company but since it's under the same corporation, we are all housed in the same building but different sections. She was a stunning woman who was full of confidence...still she was only in her late 20s when the escapade we had took place. I can still remember her perky breasts (they were not too big, B cup) but her nips are nicely pinkish colored as her skin is quite fair. She is ethnic Chinese btw... But her butt is to die for, round and perky with really smooth skin. I especially remember the doggy we had (which was her favorite position), both standing and on all fours. She liked it very much when I pound her hard, really hard and fast from behind! She had this really juicy and wet mount which seemed perpetually ready for action, not to mention the tightness that grips my LB when I thrust it in. I was younger then and was full of energy. The problem is I couldn't hold it in long enough each time to keep on pounding...always blowing my load too fast...

I actually can't really remember how we hit it off and why she even picked me, she was quite petite and she told me she likes big and well-built good-looking men (maybe I fitted the criteria). I knew she already had a bf at that time and if not mistaken she was like 6-7 years older than me. She did all the leading and all the moves that leads me to at least 4 sexual encounters with her. Once in a motel, once at her friend's place and twice in her office over the weekend under the pretense of having to work over-time. I can still remember vividly the first time a girl taking my load in her mouth and actually swallowed it all...and that took place in her office with me sitting on her chair and she kneeled in front.    I have had a couple of girls before who took my loads in their mouth before but non swallowed and when this lady did that...I was blown away!

But still, I think I didn't do my best to make full use of all those opportunities then as the sessions were rather short (as her boyfriend checks on her quite often) and I was rather inexperienced ...if this happens to me now, it will be completely different for sure.

She ended the escapade soon enough and I learnt she was actually in preparation to get married with her bf when she "used" me. I guess maybe she was looking for some ways to release some stress and pre-wedding jitters by using me...but good learning experience for me nonetheless. I was actually starting to fall in love (more like loving to shag her) with her after the 3rd encounter... After she got married, I tried to get her for more, but she just shrugged me off...have to admit I was kinda sad...

Any other bros have similar experience and would like to share?  I think if it could happen to me, there will be many more similar experiences out there. One thing which I am not sure why or how, I seem to attract older women. Counting this lady, I had and ex-gf who is 2 years older and my wife is 3 years older. There was another lady who was 8 years older but also hot as hell, but unfortunately nothing happened with her even though the sexual tension with her was unbelievably high! I knew she wanted me, but she was too scared to go all the way... it was one of those big catch that got away...

Similar but this was when I was on a expat forum of HK where I had planned a drinks get to gether for all online forumers to break the ice. There was this woman who owned a BMW and she made it known to a lot that she liked driving around town in her Beamer.
So we all met in Stormy Weather and this woman (lets call her BWM) so she stepped into the bar and introduced herself.  Fast forward, we all had a good time chatting and this woman of 44 years at the time (I was 32) got talking to me and we spoke a lot . Found that she was married but her husband was handicapped and she is out to relax.

One thing led to another and she ended up giving me a lift back to my home on New Year's eve and I invited her home for a cliche-esque coffee and we ended up staying awake all night making love. If that was not enough, we continued till the afternoon of the new year's day. And man that was some time we had - with me going on overdrive in every way I could.

In following months we must have met at various different places - hotels, her home in Tai Po, in parks and every time we were high on the sexual drive . Heck we even made love in the cinema watching a movie I could care less to remember.

On her birthday she invited me to her place with other friends and thats the evening I found she has a daughter. It was quite a matter of factly opening "hey P.. meet my daughter".  Till that night, she had not mentioned anything about her daughter but that was an eye opener.

Over the years (2 years I guess) we were still in touch and still shagging on and off in our sexual overdrives. There was a lull and then one fine day she told me she has found another man and that she was to marry him in 4 months time. Strangely I was not disappointed nor jealous nor felt any sense of envy. Even attended her wedding reception and she still had that twinkle in her eye as she saw me coming over to the reception altar.  But I left it at that  and never bothered to contact her again. All's well, ends well.

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When I was 25, I used to attend ballroom dance lessons and there was this student dancer from Belgium (I think she was 45+) . All students decided one day to go into a big mexican restaurant where they had a live band and a huge, really huge place for dancing and partying .  The band played some Chacha / Rhumba numbers and (Adele) casually asked me if I would be willing to dance with her. I obliged and with the kind of dance Rhumba is, there is a big scope for being in close contact with your partner. That's what happened and my 25 year old hormones were racing and raging . She could feel the bulge and was responding aptly and her eyes were doing the dirty talking then. Heck the bulge in my pants was a feelign to remember and she whispered "my my, another member wants to come between us, can I take him after we party?"

It was late by the time we all called it a night. Adele and I were high on our drives but I suggested we take a small walk on the waterfront . We did that.. and late into the night 1 or 2 something.. we were making out , touching each other and feeling our bodies in full view of Victoria harbor. Not a soul was there at that time except for a few boats bobbing up and down and a distant bark of a dog on some fishing boat.

We met again a few times over dinner and were completely in sexual bliss with each other - and for a 45+ woman from Belgium, she was a stunner body ! Our last love making session was at the church near the American Embassy on Cotton Tree Drive. What a place and what a night it was.

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AFF - I must have shagged at least 5 MILFs (All Chinese + 1 Japanese) and I am of the firm belief that a woman in her late 30s-40s is ever hungry !

Older women starved for sex as they wanted to feel they are still capable of seducing younger men.

This got me going through the mental roladex, and I realized that I have never, ever had sex with an older woman.  I wonder how common that is.  Maybe a topic for a 141 poll.  Should I start now?  

Neah... why break a perfect record.  I can keep some virginity in something.

Yes,  must confess that this topic is of great interest to me, for in my younger days, I DID get it on with quite a few ladies who were older than I. Perhaps not really an appropriate topic on this a board dedicated to paid experience with WG's i/o civvie experiences - but since such experiences do make up the whole of many a mongers' body of what makes them mongers.......!

Anyway.... when i was younger, I had always "ran" with guys who were at least 2 or 3 years older than I. But since I had grown large physically at a younger age, I never felt out of place - except of course in the deepest recesses of my own consciousness, for lets face it - I just ain't had the experiences of my contemporaries!   But I certainly made a convincing act of it!!

One of my most memorable experiences had been with a gal I met at a party when I was barely 14 - lets call her Julianna; I was having a GREAT time when a gal I knew came up to me and said - Hey SEAJ, meet Julianna, my good friend" Just like that and then just disappeared and left me with "her friend."

I stammered a few words facing this BEAUTIFUL gal with full make-up and a sexy body to boot and she in turn blurted out - "Oh, I'm a Secretary at XXXXX (quite a well known large Company)!" I don't know why she told me this as I know I never asked her the question. LOL!

Through the course of our "relationship," she had told me that she was 18 - but I'm 99% sure that she was quite a bit older than that.  Now you guys are probably gonna say - "Harumph... an 18 or even 20 YO gal ain't nuthin' - she's a pup herself!" Yes, right now I do see how she was just a young un' - but I was barely 14 - and to me then, she WAS the archetypical experienced older gal.

She introduced me to a whole new world of "grown-ups" with taking me to all sorts of Clubs (which even my older friends couldn't get into/not even aware of), Love motels (and many a session on top of her building in the staircase next to the Lift machinery, or other "unique places" even at the woods on the slope of Broadwood Road which was then not as well developed - as my school boy "allowance" even supplanted by her quite generous and frequent subsidies cain't always afford a love motel!) - and best of all a whole gamut of REAL SEX i/o of the usual grope, insert and WHAM that is the usual modus operandi of teenagers.  

Slow, soulful, intense sessions when she taught me the art of making her really feel good (of course including and foremost - DATY!!) and returning the favor by giving me some of the most memorable blow jobs of my life; and oh yeah - rimming, which she referred to as "round-the-world" as she would flick round and round my nether regions prior to thrusting her tongue full bore!! Omigawd - I can still remember that even today!!  (Anybody here know if anybody else uses this term "round-the-world" to describe rimming? I've not heard it being used except by her).

And from her, I got "exposed" to a variety of other rather older friends both guys as well as gals; and thus for a couple years prior to my going off to University overseas, I had basically been well "taught" by quite a few older ladies.

My kudos to the older women of our lives!!

SEAJ

[ Last edited by  SEAJ at 29-11-2011 13:06 ]

Great experience I must say you have there p_diller! I find myself wishing for the same experience like you...

You are spot on when you say women in their late 30-40 are ever hungry! The fact is, this is the age when they have matured to the level that they are confident enough to get what they want and knows how to ask for it and enjoy it the same time. To me, a women with confidence is a turn on. But I know many men find confident women intimidating.

You are one lucky dude to have the opportunity to meet someone who ultimately becomes a fuck-buddy of sorts. Good too that you don't feel anything when you learnt of her marriage, that means you have achieved the highest possible level of maturity in having a fuck-buddy!

Wish I could find one like that as well...

Yazoo, if you ever come across a MILF you just gotta have...I strongly suggest you give it a go. Lose your "virginity" on this one...it will be worth it. But please make sure the MILF is hot and willing!

SEAJ is right about them older girls even smelling different. The younger ones do have something the MILFs don't have...namely youth but nothing can replace experience and confidence! All MILFs I know so far have been great except for the one hot mama that got away because she was to scared to go all the way with me...I never get to find out if she is great in the sack. But from all the flirting and sexy looks and talks we had, I'd reckon she may just be a wild thing in bed...

By the way, do you know women's body doesn't age as fast as their face?

[ Last edited by  Tuffbod at 29-11-2011 18:05 ]

as this is non-mongering related, you may continue your discussions in Veggie Cafe

The dust collected here is getting thicker by the day

It's been a while since any bros added more stories here... I am sure there must be more from all you bros out there. So if you have, let's share it and enrich all of us here with some interesting ways of learning facts of life from some MILF that you encountered upon...