Age is just a number

[geordiekev]

Tell us about your first fuck and your age gap between you and any fucks.

My first ever mature lady was my neighbour when I still lived at home with my parents. She was about 4 years older than my mum. Joyce would be about 47/48ish. I was in my late teens and would fantasise about her. One day she caught me in their house(we had a spare key so to walk there dog with ours), me dressed in her undies & heels wanking away on her bed. I was so embarrassed but she kindly & coolly stripped and joined me in her bed and took my virginity. That was a start of a 6 yr relationship.
My 2nd mature lady was a neighbour of my now wife's & myself. Her hubby had been real poorly, I would often speak to Dyllis over our garden fence or sometimes if the weather was rubbish, we'd pop into each others houses. This particular day, we're in hers and we're talking about this and that when she just kissed me out of the blue. WOW, I wasn't expecting that, she then started to apologise but when I went in for our next kiss, she knew she didn't need to apologise. We ended up naked in her bed, fucking like rabbits. I was around 29, she was late 60's. Even all these years later, we still meet up for a fuck, especially around this time of year.
Now I'm married(2nd marriage) to a gorgeous woman who is now 70, to my 44.

[joker1961]

My first experience with an older woman was by shear accident. I was 21 she was 48 and smoking hot . I was the bar with my best buds drinking and saw another friends mom drinking at other end of bar. I walked over to say hello just to be polite because she was looking my way. My 2 friends stayed at other end of bar because they didn't know her that well.
We chatted up a bit then I offered to buy her next drink . She had 2 lady friends who were sitting with her talking between them selfies who from time to time would look over say something to one another and giggle. I didn't want to intrude on her night out so I said goodnight and wandered back down to my friends. When I got back to my friend they both asked who are the milfs. We all laughed and continued drinking.
About an hour later both my friends decided they wanted to head home because it was slow at the bar and figured they wouldn't begetting laid so off they went. It was a neighborhood bar so I decided to hang back and have a couple more beers before I left. The bartender brought me a drink I hadn't ordered and said it was from the pretty lady at the end of the bar. I looked down an it was my friends mom sitting by herself . The bartender was right she was a pretty lady. He friend were kind of sl*tty and must have left with the drunk old guys they were hanging all over to get free during the evening. I felt bad she was sitting alone so I got up and joined her.
I asked if she minded if I joined her and added that the prettiest lady in the bar shouldn't have to sit alone. It wasn't really meant to be anything more than a polite compliment but she lit up and became extremely happy that I said it. We started talking about a million different things and even started dancing and have a good time. I had noticed she started touching me more and more and well I started doing the same. At some point the night was coming to a close. I have to admit I was a bit bummed out she was a great person to party with.
I escorted her to her car She was a bit buzzed and asked me if I could drive her home. She lived on the other side of town as was afraid she was to drunk to drive . I was buzzed but said sure as long a I can take your car home so I wouldn't have to thumb back from the other side of town. She told me if I prefer I could crash at her house because her son was spending the night at his girlfriends so I could us his room. I had slept over there when I was younger but it had been years ago when I was 10. I said sure why not. She wrapped her arms around me and pressed her very large breast against me. I am 6 feet tall and she is about 5'1. I was caught of guard by her hug but couldn't help it but my cock went hard. Like all 21 year olds you get hard when the wind blows. She pulled back from our embrace looked down at my crotch back at me and said that you for this. I wasn't sure if she meant the hard on or the ride. She grabbed my arm and we escorted each other to the passenger side of the car. I couldn't help but keep staring at her amazing breast. I could believe I didn't notice her body all night. just her gorgeous face. I put her in the car still checking her out and still very erect which I was trying to hide to no avail. Then one amazing surprise from her as she sat in the car.
As she sat down she hiked the skirt she was wearing up while she slid in exposing her gorgeous legs and giving me a slight peek at her well shaven pussy. I had never seen anyone women [only2] I had been with to this point shave their pussies. I was amazed how wonderful it looked. Her lips looked very full and swollen. I almost blew my load right then. I couldn't believe she was wearing underwear at all. She again looked directly at my cock then up at me and smiled thanking me again. I shut the door and ran to the driver side as fast as I could think this was going to be one amazing trip across town.
I was right it was . I climbed in and she didn't even waste a second . She reached across the seat and grabbed hold of my cock . She smiled and said is this for me. Stunned and shocked by this I said something stupid. She smiled and unzipped me and swallowed my cock whole. I'm not huge but none of my other girlfriends ever to me down my whole length. Her mouth was heavenly. This women sucked cock better than any other woman to this day. What a fucking pro. I reached for her skirt and tried to hike it up to get a few finger in that gorgeous bald c*nt but it was too late . I started streaming load after load down her hot throat . She swallowed every drop which now one had done to this point either. damn it was amazing. She pulled her head off my cock looked at me straight in the eye an said lets get across town so I can suck and fuck that beautiful young cock all night. She gave me the best sex in my life that night. I will never forget that night and to this day have never had more fun in bed than I did with her that night.

[daskers]

Originally Posted by geordiekev

Tell us about your first fuck and your age gap between you and any fucks.

My first ever mature lady was my neighbour when I still lived at home with my parents. She was about 4 years older than my mum. Joyce would be about 47/48ish. I was in my late teens and would fantasise about her. One day she caught me in their house(we had a spare key so to walk there dog with ours), me dressed in her undies & heels wanking away on her bed. I was so embarrassed but she kindly & coolly stripped and joined me in her bed and took my virginity. That was a start of a 6 yr relationship.
My 2nd mature lady was a neighbour of my now wife's & myself. Her hubby had been real poorly, I would often speak to Dyllis over our garden fence or sometimes if the weather was rubbish, we'd pop into each others houses. This particular day, we're in hers and we're talking about this and that when she just kissed me out of the blue. WOW, I wasn't expecting that, she then started to apologise but when I went in for our next kiss, she knew she didn't need to apologise. We ended up naked in her bed, fucking like rabbits. I was around 29, she was late 60's. Even all these years later, we still meet up for a fuck, especially around this time of year.
Now I'm married(2nd marriage) to a gorgeous woman who is now 70, to my 44.

I was in high school so was she! The year was 1983. A year after high school, I ended up fucking a lady who's husband was in the county jail, she was the step sister of a older friend of mine. Me and her fucked a few times, she was 38. Some years later is when I had my oldest one, I was 39 and she was 64. She was an ex mother-in-law of my brothers!

[crazyhorse91]

When I was 19 I was asked to give a new lady a ride home after work. She was 36. We were working 2nd shift. On the way to her house she asked if I could give her a ride to work the next day. When I pulled up to her house I said "well see you tomorrow" . She said "don't you want to come in for a cup of coffee or something? We fucked for about 3 months until she met a bf her age. My mother found out and wasn't happy about me fucking someone twice my age.

[mrhitachi99]

My older lover post is here so I won't take up the space here again.

She was around 40 or so and I was in my late teens. Lately I find myself thinking about that encounter more and more. Good god, she was a sexy woman! The beautiful images and great stories here making me appreciate it even more. If only I knew then what I know now, as they say!

[richyguitar]

The biggest age gap I've experienced so far (and probably ever will) was back in the days when I went to college. I had just turned 28 and I was spending my evenings down in a local pub where I regularly met a lovely ginger haired mature lady. It turned out she was 57; but pretty young at heart and I really enjoyed being with her, talking about music, laughing, havin a few drinks together... One night, closing time was near, she eventually invited me to come with her and so I did. Walking along the way, I was totally thrilled by the thought that she might be in for more than just another drink, but pretty much because of our age difference I was far from confident about making the first step. For sure we had spent some evenings with great conversations, but there had never been any kind of physical contact between us.
When we arrived, she offered me a seat on her sofa and disappeared for while before she came back into the room with a nice longdrink she had mixed for us. She sat down beside me and it didn't take long until she started fondling my arms and thighs. Soon we were kissing each other and she took off her black top first, then her bra and before I had even time to realize I was fondling and kissing her mid-sized pale white and slightly freckled breasts. I ended up with my pants down and she gave me an enthusiastic blowjob until I blew my load in her mouth. She knocked it down with a slug of her drink and seemed absolutely comfortable with keeping her pants on that night. She went back into party mode and stayed topless while we were talking, drinking and I was allowed to touch her breasts and nipples whenever I wanted to. It was one of the most incredible nights in my life and I made up for it the next day. We finally became very close fuck buddies for about one year. We kept seeing each other 2-3 times a week and were just going at it like crazy teenagers... she's a really great lady.

[dftemp]

I got an hj from a lady 30 yrs my senior yesterday. I came twice with very heavy loads....and noisily. Her husband was downstairs, and must have heard.

[Minimusminimusminimus]

I normally go for girls my age or younger, but twice I've nailed cougars (and maybe one or two more when I was in the military, but those memories are fuzzy due to alcohol ).

The first one was quite interesting. Probably my greatest day sexually ever. I nailed my 24 year old girlfriend after we worked out at the gym. She was cheating on me and I knew it, but she was a great fuck, so I decided to continue in it and just fuck other chicks too.

She was a bartender and had to go to work, and I was off. So I went over to a friend's house who had a pool. A girl from work was texting me about her jerk boyfriend, so since I'd been eyeing her for months I told her to come by and bring a swimsuit. Well, the 18 year old hottie showed up... with her prick boyfriend. Lame. Anyway, apparently she wanted to make him jealous because she kept rubbing on me and flirting obviously. He was the smallest marine I've ever seen and though he looked sullen, never said a thing! Long story short, I took her into a room and we made out. I kissed her all over and she gave me head.

Later the same evening I went to a dinner party at a lady's house I had been invited to. It was being given for some German college students that were hiking a local trail and were in town for a few days. Two couples, although I didn't know at the time. I had my eye on one of the girls, but it soon was clear that one of the guys was with her. She ended up getting a little sick, so the Germans all went back to the hotel. There were also a couple girls my age there who lived next door. One was a wet dream, but I could never quite figure out if they were gay. At any rate, they left too.

I figured I'd be nice and offer the woman who threw the shindig help doing the dishes and cleaning up. She was a blonde, 45 or so, well built with large tits and a nice ass. She was good looking for a 45 year old, but no thought had even crossed my mind about screwing her. After we cleaned up we chatted for a few minutes an I was going to leave as well. She thanked me for being so thoughtful and told me I was welcome to crash in her guest house since nobody used it and it was late. After considering, I accepted. She got me some blankets and we said goodnight. When we hugged the whole atmosphere became instantly sexually charged. Without even thinking about it I kissed her and 10 minutes later clothes were all over the floor of the front room of the guest house. We weren't quite naked, but both were moaning and panting and kissing and grinding. Her bra was under her tits and she still had her panties on. Just then, the two neighbor girls came over to discuss plans for the next day. Since it was summer, only a screen door was closed between us, and they had a full view of our passion.

So... we didn't fuck that night, but apparently she hadn't been with anyone in a couple of years, so was ready to have me over soon and often. I think I nailed her the next night, the night after, and she wanted it in her ass the third night. That was the only woman I've ever been with where I could cum and keep fucking as if I never had. She kept me hard for hours. I once came in her mouth three times seconds apart ( best and most unusual orgasm ever!) And still was able to fuck her!

Wonder what ever happened to that chick?

I know I said two milfs, but this is long, so maybe later I'll tell you about my mom's friend. Haha

[xxxxenophile]

Originally Posted by richyguitar

We kept seeing each other 2-3 times a week and were just going at it like crazy teenagers... she's a really great lady.

That sounds like an ideal relationship with an open-minded cool chick!

[explorer98]

The other enduring feature of my life!

I've been fascinated by older women as far back as I can remember - which in this context goes to infant school. At that age, I didn't know what was behind it, just that I liked things - that others clearly didn't get!

I was brought up in a house which was frequently full of women. My grandmother was a dressmaker and so the place was often busy with various ladies trying things on and having adjustments made and of course they didn't bat an eyelid at stripping down to their undies with a cute 7-year-old around (I was then, really!).

I still maintain that's where it started!

Of course it was years before it became sexual but I noticed even at 11-12 that I fancied my then-girlfriend's mother more than I did her!

At 14 I had a fling with a friend of my mother's. She was 24 and though we never had full sex, we spent a lot of time naked together and I got to thoroughly explore and enjoy her ample body - until her parents kicked off and came round for a row!

After I left school, there was a woman at work - in the same factory as me - who worked different hours, coming in later and leaving earlier. She'd go to the canteen and change into bib and brace overalls and I found her quite fascinating.

I found out she was 59 (I was then 16) and although quite old-fashioned in her ways and appearance, she was always very smart, immaculate makeup and very carefully dressed.

We got to know each other and got on more and more and I'd deliberately hang around when I knew she'd be changing. Eventually I pushed this further and found things to be doing where she was changing and was pleased to find that she simply continued - and she was wearing stockings and suspenders the whole time!

She always wore very red lipstick and I commented (positively) on this and other things a few times which she clearly found flattering. There's a gap in my memory here but somehow we ended up kissing - quite innocently at first but it became deeper as time went on - and after a time, she let me touch her bare thigh above her stockings (I've NO idea why!) but the real coup as far as I was concerned came when she let me slip my hands into her overall and hold her breasts!!

We'd do this by the canteen door which gave us a good view of anyone approaching and I'd nibble her neck while I rolled her nipples. From the weakness in her knees, she clearly loved this and we soon progressed to her playing with my rock-hard 16-year-old cock while I enjoyed her tits.

It never went any further than that and we lost touch when I left the company (1979!) but she was a treasure and I'll never forget her. After that, I was completely incurable!