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She was a wild one
Posted:Nov 25, 2020 10:32 pm
Last Updated:Nov 26, 2020 1:20 am

about five years ago, things were bad at home. So I put out a post craigslist looking for an online girlfriend with. I never really wanted meet this person. I just wanted have that "dating" experience again.

I posted in Pensacola because that felt close enough have similar experiences, but far enough likely never meet.

That's when "CB" sent me an email. She was 66 years old but open chatting about everything. I was interested so we chatted and things developed into affection and we started doing some cybersex type stuff.

She was very experienced in her sexuality and was very open to discuss everything with me.

Then she revealed "how" experienced. She was married for 30 years, until she started having an affair with a co worker. so she divorced her husband to be with him. except she never stopped sleeping with her husband. Strange to me, but whatevs. I'm just now starting to open my eyes to the world and we weren't actually dating.

We continued chatting throughout all the orgies her new bf brought her to. she'd tell me stories of the gang bangs, sitting on phone meetings with him eating her out, fucking the young guy who came to pick a package.

I was fine with of it.. i really was. But then she wanted meet. Fantasy meets reality... I wasn't prepared for that. I'm pretty confident about myself, but after two years of stories listening to her talk about getting pounded in holes with 9,10, and " cocks, I had zero confidence...

I kept putting it off. but then she got cancer and her life turned around and she went back her husband. we talked occasionally, but nothing like before.

She confessed that she wanted leave that life behind. she wanted commit her husband only and maybe an occasional visit . Apparently she had really developed feelings for .

I still put her off.

last year around june, we started talking heavy again. she was only with her husband and her old bf was out of the picture with his new gf. her husband was leaving for a trip in early july and if I could find an excuse go see her.

I committed.

two weeks
1 weeks
6 days
5 days... i get a message

the bf is back in the picture... and the gf... and the room mates... and co workers... and other people.

She can live her live, and I wouldn't judge her for it. But I didn't want be another person in a crowd. so we talked and dedcided part ways. She didn't owe anything and I didn't want her wast her time coming around.

but damn she had big boobs and I just couldn't get her out my system. I'd email her a few times and we'd a little. especially with her cancer recovery and covid I wanted check in.

but in September, I realized I had a problem. I couldn't get her out of my system, even now I think about her. I sent off a final email telling her that I was done with this email... I deleted the email and officially lost her contact info...

i both regret and am happy that I was so impulsive. I couldn't get past her and I had never met her. Hell, I'm still not 100% it was even a woman. I mean, she sent pics and all. but who really knows.

my last email did have my new email address in there. so maybe I was a bit of a chickenshit.... probably a lot.

Anyone else have a person they just became addicted ?

and if anyone thinks I judged her on any of her exploits, you couldn't be more wrong. It was a period where I really learned about sexuality and started putting thoughts together about what I liked and didn't like. She helped through that and I'll be enternally grateful (and she knows it).
Attempting to take a V card
Posted:Nov 24, 2020 8:52 pm
Last Updated:Nov 26, 2020 1:20 am

dating my girlfriend for 8 months and we finally had the discussion on sex. Although we were both in college, I had only recently lost my virginity and she still had hers.

Things were going okay between us and we lay on the bed kissing. This is the only girl I've ever dated that would wear short skirts and you know my hand was all up in there.

Her panties were off and after fingering her to her second orgasm, I had her top pulled up and softly sucking on her nipples. She's pulling my shirt off of me and i'm unbuttoning my pants..

do you have a condom, hell yeah i do. i reach over and before i open it. I made the "nice guy" mistake. "are you sure?"

tears... no, not really. damn it. we talked for awhile and finally discussed that the sexual activity had kept us going and the dating had lost its flair. in the span of an hour, I went from tight virgin pussy to not having a girlfriend.

Honestly, I don't regret it. I'd rather lose out on sex than be remembered as a regret.

Side note: She did hook up and lose the card to a friend of mine. she confessed it was her biggest mistake and was glad I didn't force the issue when i had the chance. Then she married a complete asshole.

but damn I miss those short skirts
Overeager injuries
Posted:Nov 23, 2020 8:38 pm
Last Updated:Nov 26, 2020 1:20 am

I'd been traveling for 3 months and when I got home I was so happy jump in the bed. She was down for it too. a big kiss as the airport terminal, kissing on my neck at each stop light, rubbing my leg in between.

pulled up to the apartment and didn't even bother to get the bags. ran inside stripping clothes off as we got to the bedroom. one last leap to the bed and saw the new end table that collided with my knee mid flight, twisting me around and slamming my foot into the bed frame...

no stitches needed, but the foot had fractured bones and walking was a pain. had wait another couple of days get that sex we needed...

but went a little slower the bedroom. side benefit was that all the extra pain helped control my orgasm so we had sex for quite some time... even if i had stay on bottom (i wasn't complaining)

Although I didn't need stitches, I do still have a scar.
First time I Fucked someone
Posted:Nov 22, 2020 10:16 pm
Last Updated:Nov 26, 2020 1:20 am

I'm counting this as the first time I had sex after losing my virginity, when the nerves were a less prevalent.

We met in an aol chatroom... yeah.. this was awhile ago.

I met her at her work and followed her home. she wanted jump in the shower and freshen so i sat the sofa and watched some tv. she came out wearing just a towel so we started making out and i started to pull her towel down to expose her tits.

She was the chunky side and self contious. so we backed a bit and we just talked while i ran my fingers and down her leg. She pulled the towel down her own and i made sure they got some loving (again b cups, but quit tasty still).
I moved my way between her legs and as she started get into it, she requested we move to the bedroom.

but she was perfectly happy with contining go down her until she cam, then she pulled onto the bed laid back and reciprocated the fun. she is the only person this day that spent do much time sucking and licking my balls and underside. I just wanted make sure I didn't cum in 2 minutes and I was focused that and still trying enjoy myself. I told her I was getting close and asked what she wanted to do.

her had at the base of my cock and stoking it as her lips moved and down. the groan preceded the cumming and she didn't waste any. she went off the bathroom get a towel and brought one for .

it was wasted because i went right back being chin deep into her shaven pussy. I could feel my body recovering so I grabbed the condom I brought, put it on and climbed on top of her.

I know condoms decrease the sensitivity... but when she was that tight, i felt everything. This was the first time i felt "in control". i was able to go deep, pull out to tease, then back deep to really feel her groans.

got to try doggy style a little... she an extra cushiony booty, so this didn't really feel great. plus it was the first time (next time felt better).

ohhhh then she got on top of me and took control. a bigger girl on top is an amazing thing. eventually, too much pleasure got the better of both of us.

another amazing orgasm

we hooked a few times. a couple more firsts with her.
Boob size, overrated?
Posted:Nov 18, 2020 3:01 pm
Last Updated:Nov 25, 2020 6:42 am

On some of my blog posts, I've made comments that I want be with a well endowed woman, at least once. I've generally been with the A or B cup, regardless of their figure. I've never been picky about a woman's size, but always end up with women on the smaller size.

Is this something I'm just over hyping in my head?

curious guy is happy with what he has, but can still dream

judging from the poll results, it seems that boobs are just awesome. enjoy them whatever size they came in. #notashockingrevelation
Be happy with what you get.
Bigger is better
Smaller is more fun
All you need is a handfull
Go big-big at least once.
0 Comments , 4 votes
The first affair... almost
Posted:Nov 17, 2020 9:18 pm
Last Updated:Nov 18, 2020 3:02 pm

Back before craigslist became completely dominated by bots, I met a girl and we talked for about months.

She was 7 months pregnant and her baby took off 5 months prior. We had been talking and she needed sex and I was on a 3 months dry spell.

She was a curvy girl and the more we talked, she was looking forward to eatting her pussy, which he would never do and I was looking forward her DDs. I love big boobs even though every woman i've been with has been in the B sting club.

We figured out a good time meet at her apartment with her asleep and I would be out "see a movie."

I headed over and no answers... I finally just went and saw the movie. The next day she sent a message that baby called her and asked her come visit. Things didn't work out well for her and she wanted re-establish a connection...

But as much as I wanted big boobs, I don't put myself in a position be stood up twice. One day i'll get by big boob experience. *Y*
exceeding expectations, but porn still isn't real
Posted:Nov 16, 2020 2:40 pm
Last Updated:Nov 26, 2020 1:20 am

One of the benefits of being 20 and still a virgin is you have a lot of time to plan out "what to do" during sex. The downside is your reference point is porn, not exactly the real thing.

The first girl naked in my bed was cute, small breasts (apparently I set a pattern early) and a nice booty. I had received a blow job before, but i just wanted to eat some pussy for the first time.

I pulled her yellow panties down and went to down to the sweet spot. I was doing everything I had ever remembered watching or reading. sliding a finger in to massage her g spot while using my tongue and lips to stimulate her. I even pulled out the Alphabet on the clit. Then I heard the words I had been dying to hear, "OMG i'm going to cum"

Then I said the words I'll never forget..." hold on I'll get a towel". facepalm

That was when i learned that women "came" differently then men. she was patient enough to yell out "no stupid, don't stop". so i didn't and she came, I lost some hair too.

afterwards she said "I was going to ask if you were lying about never going down on someone. Because I never cum that way (not sure if lying) and that felt so good. then you did that dumbass thing and I knew you weren't."

fortunately I learned from that mistake and never really expected things to live up to the "dream of porn" now that I'm older, I imagine a squirter is fun.. but messy.

This story always makes me laugh..hope you were able to get a chuckle out of it. 18 years ago, I've learned a few new things since. like laying the towel down first... jk
On the way to the chapel
Posted:Nov 13, 2020 2:51 pm
Last Updated:Nov 26, 2020 1:20 am

I was off at a work trip in Nashville waiting on my flight. One of my coworkers met me in the terminal as she had the same flight. at 11:30 pm, our flight was cancelled. This was on a Thursday and she had her wedding rehearsal on the next day at 4:00 and scheduled to get married the next morning.

They couldn't confirm our flight and she asked if I would mind driving through the night. We grabbed a car and hit the road at 1 in the morning.

At 4am, the delirium set in and we loaded up on caffine to stay awake.

a game of would you rather popped up and she kept asking me about work people I'd rather do. Then she included her own name with someone obviously not in her league. I declined to answer...

About an hour later she said we could pull off somewhere and get some sleep if we needed to. Luckily I was smart enough to recognize this as a HR nightmare, so I kept driving.

I've never spoken of this experience but she has made reference to the other games we've played in the car.

I certainly don't regret passing up the opportunity (if there even was one) but damn, why did all these opportunities pop up AFTER I was married.

Anyway, she made it in time for her Halloween wedding and I think their divorce paperwork was filled out by that Christmas.

I probably saved myself from getting my ass kicked from a redneck. She has remarried 4 more times since then. It might have been one of the smartest things I'd ever passed on.

so, was I reading too much into it or was I smart to just keep going.
Ouch Ouch Ouch
Posted:Nov 11, 2020 9:26 pm
Last Updated:Nov 26, 2020 1:20 am

I always thought blue balls were a made thing...

The story starts with my high school crush that kind of just kept the hook my junior and senior year. After going college, I got a girlfriend and suddenly she was interested.

junior year of college (now single), I had drive Tampa and she lived and Tallahassee. Wanting reconnect I figured we'd meet for lunch while passing through, but she offered let crash at her place and break the trip.

I still think she has the hook so I'm not expecting anything. Watching a movie I start rubbing her back and leave it at that. Now it is bed time so I figure I'm the sofa but she invites her room and hops in the bed with clothes , i do the same. Still not thinking anything is going happen.

Now the stuff you are interested in.

She snuggles into the little spoon position and tells how turned she was getting with rubbing her back... I start rubbing her back some more, her shoulders, her butt, waist and her breasts. at some point I started kissing her neck, I lost track.

she turns face and asks that I be gentle with her breasts, they've gone a size recently and are quite sore. We start kissing and I slip a finger inside her.

kissing her neck some more I slide another finger in rub her clit and turn her more. She moves her hand down mine and pushes a 3rd finger in. i practically have my whole hand inside her and it is soaked.

I'm kissing her nipples and breasts (gently) and she arches her back for a deep moaning orgasm.

she gives a kiss, sits , adjusts her shorts and top, says "wow that was great" and rolls over to go sleep.

wait... huh? am I really getting nothing?

not wanting to push matters, 1) it's wrong, 2) i realize this is a hook manuever, 3) i'm a little bitch.
I go to sleep.

about an hour later, it feels like my testicles have retracted into my body and are attempting to get pulled out from every direction at once. just so much owwwwwww

I had to stumble to the bathroom and jack off. I remember it wasn't even a good jack off. like it was surgical and it hurt to even do that.

I never got an answer as to what the hell happened. I got put on the hook again, it sucks. took me another 5 years to finally break off.

But I'd tap it in a heart beat if I ever had the chance.

Anyway, I've always thought this story was kinda funny. I have a few more funny ones if anyone is ever interested. I've dropped off of here, but might post more on occasion. at area dot ventures404 at . I'm the google too.

I'm a believer of bad things can happen, but they generally can make good stories out of them if you are willing to be light-hearted.
Finding the fire again
Posted:Oct 30, 2020 10:15 pm
Last Updated:Nov 10, 2020 2:36 pm

A couple ago I attempted find an online girlfriend that lived a few hours away from . I wasn't prepared for an affair but needed share my life with someone else... Very easy thing say with low expectations. But I found an amazing woman older than .

We've spent the past few talking regularly about our lives and relationships. She was very adventurous and we became confidants on all her sexual adventures. She and her husband were swingers and she would describe the lifestyle .

A couple months ago, I had the opportunity meet her. we were both nervous and when we looked into eachother, it was like seeing an friend... and I went for it, a gentle kiss on the lips.

My body came alive and all I wanted do that day was hold her body close mine. A five second kiss felt like minutes. I pulled away and she pulled be back for another eternal bliss of a kiss.

I felt alive again. I love my wife, but this was new and exciting. since then I've been wanting meet with her again, but what was initially a safety blanket of distance is now a barrier of pleasure.

She recommended a few website for me find someone new and local. Here I am, looking for the fire once again and hope find a woman who can recreate the same lightening again. and honestly, just having that confidant of anything was so amazing have.

That is laid on the table. These blogs may not do much, but it is cathartic. And everyone could use a release.

To link to this blog (areaventures404) use [blog areaventures404] in your messages.

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