Author: ayoungamerican02

Mature Kindergarten Teacher . . . Young Man . . . Hotel Room [MF]

Ok, a new post after my recent reposts…

Me: tall, gawky kid growing up, with glasses and an overbite. Then wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles–I’m 6′, brown hair, blue eyes, fit), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged, and alternate between overconfidence and no confidence.

I’ve been going through a stretch lately where I’m happy with my friends, I’m very busy professionally, and I’m not looking for a relationship…but I am human. However, I guess I’m a little unusual in that I do primarily prefer, if I’m going to strictly hook up, to hook up with women older than me (I’m in my late 20’s)–it’s intrinsically established that this will not evolve into a relationship, they seem to enjoy having a young energetic guy to play with, and I enjoy the maturity and lack of pretense (and definitely having absolutely no pressure to turn it into a real thing). Also, it’s just a little kinky–being with someone I theoretically shouldn’t–and I like that, especially because I’m pretty straight in real life. Read more »

College: [F]ingered with Dad in the roo[M]

[Repost from my previous account. I’m going to put up a few of my previous posts to fill in my history–leading into new posts about other experiences I’ve had.

A lot of my posts are going to be about me and older women–I just find those sessions sexier or easier to describe for whatever reason. Being with someone unexpected, I guess. With girls my age I guess it’s more your typical meet through friends or catch each other’s eye on a night or. And I of course have relationships with girls my age. The below is about the my most serious girlfriend and a memorable time with her.]

To just start with a little background, I was a tall, gawky kid growing up, with glasses and an overbite. Then I wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence. Read more »

Late 40’s [F] and the college boy [M]: A first for both of us Pt. 2

[Repost from my previous account. I’m going to put up a few of my previous posts to fill in my history–leading into new posts about other experiences I’ve had, too.]

As a refresher, I was a tall, gawky kid growing up, with glasses and an overbite. Then I wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence.

Again, Kim was in her late 40’s, curvy but not fat, maybe 5″4″ with a cute, youthful face (smooth skin, no wrinkles) and gray and white hair, cut kind of in a fashionable bob haircut. I should define fashionable bob, because it’s basically the hair style that it seems women over 35 have–where it’s kind of longer in the front framing her face and then gets shorter toward the back (I find it the perfect mix of cute/professional/sexy). Medium skin color, kind of reddish like she had a tan that was fading but still had the freckles. She had wide hips and a large, very nice ass that still had some perk to it (though larger than what I was used to), and–by my estimate–double d breasts with fairly large areolas and eraser-like nipples. Read more »

Late 40’s [F] and the college boy [M]: A first for both of us

[Repost from my previous account. I’m going to put up a few of my previous posts to fill in my history–leading into posts about other experiences I’ve had, too. For the impatient I’ve placed an **action starts here** below, as I realize this is long.]

Should probably start with a little explanation. As I was growing up I was tall, gawky, had glasses and an overbite. Then I was a wrestler throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence.

I remember hearing my dad and his buddies laugh about how ridiculous and unrealistic “I can’t believe it happened to me” letters that were in Penthouse (or Playboy? Both?) and that’s kind of how I feel about the experiences I’ve been fortunate enough to have–I don’t consider myself overly sexual or deviant, but I’ve somehow managed to have a lot of encounters that, upon reflection, are large in volume (everything from college girls to probably an unusually high amount of milfs/cougars) and kind of unusual (in semi-public rooms, fingering under the covers in front of the girl’s family, threesomes, with food, tying up, and so on) and seem like bs. Read more »