First time with older woman?

[zotique]

I have always had a fantasy about losing my virginity to an older woman. It didn't happen, I first fucked a girl who was about a year older than me.

I used to have the hots for a lady I delivered papers to when I was a teenager but of course it was all in my mind and I used to jerk off in the bushes on the way home I got so horny.

But I'm curious, did any of the men here get initiated into sex by an older woman?

The lady next door, your mom's friend, a stranger?

How was it?

 

[Justfantasies]

I have always had a fantasy about losing my virginity to an older woman. It didn't happen, I first fucked a girl who was about a year older than me.

I used to have the hots for a lady I delivered papers to when I was a teenager but of course it was all in my mind and I used to jerk off in the bushes on the way home I got so horny.

But I'm curious, did any of the men here get initiated into sex by an older woman?

The lady next door, your mom's friend, a stranger?

How was it?

It was great and I came buckets

 

[wildwifey]

Don't assume its all in your mind, young man. Some of us older women are thinking the same thing and we might be "jilling off" just after you leave, just as you are jacking off right after too. Food for thought...

 

[Justfantasies]

Don't assume its all in your mind, young man. Some of us older women are thinking the same thing and we might be "jilling off" just after you leave, just as you are jacking off right after too. Food for thought...

Giggle -my wife, who is a college teacher, tells me how hot some of the young men she teaches are, and what she does to relieve tensions

 

[Samisstout]

Giggle -my wife, who is a college teacher, tells me how hot some of the young men she teaches are, and what she does to relieve tensions

Now that's so hot !!



When I was 18 I fucked my Sgt she was in her 30 , Dominican . She taught me a lot about women . She was a total slut and she fucked a bunch of marines in our unit . It was fun times

 

[LIVINRFANTASIES]

D(.)(.)

Don't assume its all in your mind, young man. Some of us older women are thinking the same thing and we might be "jilling off" just after you leave, just as you are jacking off right after too. Food for thought...

D(.)(.)---------- I enjoy jilling off after seeing some young men with a bulge in their pants.
We just don't have to hide in the bushes.
I think my hubby did that when he had a paper route. Don't worry it wasn't last week.

 

[jehoram]

My virginity was taken by a woman maybe fifteen years older than I was. I wouldn't have had it any other way. (And I didn't tell her I was a virgin, but I'm sure she figured it out anyway.)

 

[zotique]

It was one of my biggest fantasies as a young person and I had perhaps the best wet dream of my life with a very realistic dream of one of my mom's friends naked in bed with me rubbing against my cock.

 

[iluvboobz]

When I was in my 20s and Myspace was in its prime for meeting people, I had the chance to meet a few older women. All three had the same thing in common. They all had huge boobs, all were in there 50s, and they all were a lot wilder than the average female. I still fantasize about them from time to time.

 

[NorCalCumCannon]

I love older women

I got jerked off by a woman in her 30's when I was 18. Got sucked by and fucked a 29 year old when I was 19 or 20. Had a year and a half long FWB relationship with a 36 year old starting a 23. Had a threesome with a 38 year old and her husband at 22. Lastly, got sucked by and fucked a 50 year old when I was 25. Almost fucked a 54 year old this past December (I'm currently 27) but she blew me a little and I had just gotten my cock in her pussy when a car rolled up in an adjacent parking lot and she got spooked.

 

[Ubiquitious_too]

Hahahaha.
Check out my Post thread about virgins-
Hahahaha

 

[Nudenative]

First Time With Older Woman?

-I lost my virginity to my girlfriend who was three years older then I was, and the largest age difference was I began a brief relationship with a woman when i was 37 and she was 41. A petite native woman and she was insatiable and enjoyed being naked. We had spent an entire day nude twice at a spa in Santa Fe during that time too, with skinny dipping.

In retrospect, I do prefer older women, or women my age!

 

[zotique]

She was my second fuck, it was our first date (camping in the wilderness in one sleeping bag) and just like the first time I'd had sex, I ejaculated at the entrance to her vagina as soon as my cock tip felt the wiry pubic hairs. Shoved it in anyway.

I was 18 and she was 20 and she must have liked me despite my inept lovemaking and I moved in with her and we were lovers for three years. I was probably the only guy in grades 11 and 12 getting fucked every morning before catching the bus and every night before going to sleep.

 

[Peach102]

I was 18 when I lost my virginity to a 19 year old who was not a virgin. She was thrilled at the prospect as busting my cherry.

 

[docexprt]

I was 19 and had a good bit of experience with girls my age, when I took a summer job remodeling old homes in East Dallas, riding my motorcycle down from N Dallas every day. Two doors away lived Barb, and after her husband left for work, she'd come flirt with me. Ten years older than me, one could tell she'd been around a bit. "When you take a break, can I have a ride on your bike?" Turns out, that wasn't all she wanted to ride; God, what a freak. She soon determined my budding affinity for pussy lickin', and coached me on the fine points of pleasing a woman. Soon after we started rolling around together, I was between her legs giving her tongue action, couple orgasms, and she did something amazing. Grabbing the backs of her knees, she pulled them up by her head, presenting me her big brown gorgeous puckered asshole about one inch from my nose. Not a word, just staring intently at me, the implication was "git after it, boy" I did not hesitate, and have never looked back; almost every woman (and one man) have enjoyed my asslicking skills since then, many for the first time ever (including my wife, who was astonished that a guy would lick her butthole, she lets me indulge when we do butt sex)
That day, Barb was cooing her appreciation and coaching me up. She then showed me, with the help of one of her moderate sized dildoes, how she expected me to fuck her ass, giving me a little at a time while she sucked my dick and balls. This helped me fuck a lot of women's assholes over the years by making it a good experience, as my dick is probably a bit on the thick side.
It also helped when I got fucked myself (and fucked him), a great experience.

 

[screwher]

My wife

Heres something a bit different. I would actually like to see my wife (45) bring a young young lad (18) into manhood.

 

[MomFucker40]

Older women are always fun.

 

[DianneB]

Old women have the experience....

 

[Katieb_38]

From the female point of view I was 20 at the time and I lost my bi virginity with a woman in her 40's who was a friends mother.

 

[followmenow6969]

Old women have the experience....

From the female point of view I was 20 at the time and I lost my bi virginity with a woman in her 40's who was a friends mother.

Very nice

 

[darkpsy1986]

My first time was with an older woman. When I let her know she was popping my cherry it turned from playful foreplay to her taking over and making my head spin.

 

[peterthelicker]

Yep! Married, mother of three, 37 year old 3rd grade school teacher took my 18 year old cherry. We were in the front seat of her station wagon. It was a hot, exciting, fuck filled spring, Summer and fall!

 

[whynotjustsayit]

Heres something a bit different. I would actually like to see my wife (45) bring a young young lad (18) into manhood.

I'd like to do something to that effect if possible and hubby supports that.

 

[sevenalllin]

you will like it for sure!! when i was 19 i would cut grass for a friends grand mother she was 56 yrs.old.. i cut my self on a fence and was bleeding the cut was inner thigh near rear .she saw the blood and said in the house now and had to drop my jeans for her to clean and bandage. well instant hard on she said it's ok i've seen them before . we laughed . next week she asked about cut i told her heeling nice ty. we where haveing ice tea when i was done with grass. she said come in next she says she has not been with a man since her husban passed 10 yrs. ago and she is haveing feelings since last week would i be interested . and is blushed and said you bet, well i cut her grass for 15 yrs. after that and enjoyed every week .during winter and cold weather i'd help keep her house in repair she was by far my best F.W.B and me at 67 thinking of her after all these yrs. still gives me a hard on

 

[curious_newbie]

Not sex but when I was 16/17 I was taking a class at a local Community college. I was particularly good at math. So I started tutoring some of the students. One particular student needed a bit more help than the rest. She must of been in her 50s. One night we were tutoring at her house and it went a bit longer then expected. Long story short, we started talking about sex. She asked me if I was a virgin and I said yes. One thing led to another and she eventually jerk me off. Unfortunately I was too nervous to climax. But that was my first experience. To this day, I have a huge fetish For h my first experience. To this day, I have a huge fetish for Handjobs and older women!