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...