[FM] My Foray into Anal, and the Men who are my Kryptonite- an Overseas Adventure

I should disclose up front that for a semi-tall, green eyed blonde like me, handsome Italian men in particular have always been my kryptonite. I can offer little resistance and if they are also assertive men who can be a little dominant and insistent in the bedroom, well, forget about it… I could offer about as much resistance as if someone with stubble was nuzzling my highly ticklish neck. Wet putty.

In my late 20s early 30s I took a rather unconventional professional job overseas that had me working alongside mostly Italian men, where me, being a female with same credentials was both a definite minority as well as highly unusual amongst what are slightly chauvinist, traditional Italian colleagues. To add to that, I consider myself highly intelligent, with a very sharp wit and love of mirth and bawdiness where I can get away with it. A most unexpected combination if you factor in my typical blonde reputation. Being striking and physically attractive only added to my female advantage, and in this particular role I’m not ashamed to say that I milked my femininity for all it was worth to assist where necessary in my male-dominated workplace. Sometimes my role involved taking apart complex electronics and subsequently transporting them off for further repair or back to our US home-base, so heavy boxes. This is an example where I would make the initial effort but gladly hand off said heavy box to whatever gentlemanly, strapping Italian offered to do so. Usually I’d just have to pick it up to put it on a trolley and one would come running, “Ciao bella!” Like clockwork. *smirk* Wearing somewhat mandated short skirts, having well groomed and toned legs that I often clad in heels didn’t hurt either. I have a flair for style and definitely dressed and smelled better than the job required, I am quite appearance conscious. But I digress!

The Dating Game [mf] [oral] [mast] [squirt] [facial]

Gotta make dating interesting, or else we end up miserable and frustrated. Dating can seem ultra repetitive, especially if you’re dating some basic bitch or douchebag guy who asks you all the cookie cutter questions: Where did you grow up, did you have any pets and/or siblings, what do you do? Baaaarf.

I like to go right for the juicy stuff, which makes dating fun, but the very real downside is it makes you very endearing. Women think you’re unique, special, funny, interesting and they don’t wanna let you go. But they definitely fall head over heels, which means no trickery and no deception needed. They’ll suck your cock in the car ride home or let you finger them in the tucked away corner of the bar on date one.

But, so long as you’re being honest about your intentions, it’s all good.

I was working on this theory that interesting first dates lead to first date sex. So, I lined up a series of dates. The first date, I went all in, asking strange, silly, goofy questions instead of the boring personal stuff that ends up feeling somewhat scripted if you go on enough dates. I went out with a woman named Sasha and my questions totally caught her off guard.

That Time I Accidentally Discovered A Glory Hole [Straight] [M/f] [Young] [Teen] [Gloryhole] [Strangers] [Schoolgirl]

It happened when I was walking back from school one day.

I was an innocent – well, mostly innocent – young, teenage girl. It was a hot, summer’s afternoon so I was just wearing a little pink tank top and these tight, denim shorts with rainbow colored thigh-highs. I usually just head straight home from school but as it was so hot, I had been drinking a lot more water than usual and suddenly found myself needing to go to the bathroom.

Out of desperation, I ended up taking a detour down a secluded alley that I’d never been near before in hope that I’d find an isolated spot to pee. I followed the dirty, bumpy path down and found that it went on longer than I expected. I was tempted to yank my shorts down there and then and hope nobody would walk past and see my exposed, hairless little slit but instead I carried on walking and finally reached the end. I appeared to have taken a stroll into the countryside as there was just grassy hills stretching as far back as the eye could see, except not too far in the distance following another wonky-looking path appeared to be a public restroom. So with my backpack slung over my shoulders and my body trembling with desperation, I quickly moved towards it, my slender legs carrying me as fast as they could go.

That Time I Accidentally Discovered A Glory Hole [Straight] [M/f] [Young] [Teen] [Gloryhole] [Strangers] [Schoolgirl]

It happened when I was walking back from school one day.

I was an innocent – well, mostly innocent – young, teenage girl. It was a hot, summer’s afternoon so I was just wearing a little pink tank top and these tight, denim shorts with rainbow colored thigh-highs. I usually just head straight home from school but as it was so hot, I had been drinking a lot more water than usual and suddenly found myself needing to go to the bathroom.

Out of desperation, I ended up taking a detour down a secluded alley that I’d never been near before in hope that I’d find an isolated spot to pee. I followed the dirty, bumpy path down and found that it went on longer than I expected. I was tempted to yank my shorts down there and then and hope nobody would walk past and see my exposed, hairless little slit but instead I carried on walking and finally reached the end. I appeared to have taken a stroll into the countryside as there was just grassy hills stretching as far back as the eye could see, except not too far in the distance following another wonky-looking path appeared to be a public restroom. So with my backpack slung over my shoulders and my body trembling with desperation, I quickly moved towards it, my slender legs carrying me as fast as they could go.

That Time I Accidentally Discovered A Glory Hole [Straight] [M/f] [Young] [Teen] [Gloryhole] [Strangers] [Schoolgirl]

It happened when I was walking back from school one day.

I was an innocent – well, mostly innocent – young, teenage girl. It was a hot, summer’s afternoon so I was just wearing a little pink tank top and these tight, denim shorts with rainbow colored thigh-highs. I usually just head straight home from school but as it was so hot, I had been drinking a lot more water than usual and suddenly found myself needing to go to the bathroom.

Out of desperation, I ended up taking a detour down a secluded alley that I’d never been near before in hope that I’d find an isolated spot to pee. I followed the dirty, bumpy path down and found that it went on longer than I expected. I was tempted to yank my shorts down there and then and hope nobody would walk past and see my exposed, hairless little slit but instead I carried on walking and finally reached the end. I appeared to have taken a stroll into the countryside as there was just grassy hills stretching as far back as the eye could see, except not too far in the distance following another wonky-looking path appeared to be a public restroom. So with my backpack slung over my shoulders and my body trembling with desperation, I quickly moved towards it, my slender legs carrying me as fast as they could go.

Silver Fox Fucks a 21 Year Old [Mf] [oral] [prostate] [swallow] [creampie] [mast]

Jeff was almost 40. After a lengthy failed marriage, he looked to rebuild his life. As with most people exiting a long term relationship with the prospect of dating, he skewed younger and he had his reasons. People his age were likely also divorced and with that, came divorce drama, which he wished to be far removed from. Of course, dropping the age range down to mid 30s brought it’s own problems. Women in their early 30s wanted kids, husbands, families, the security of an older, career established male.

Jeff didn’t want to go down that route, either, which lead him to one final conclusion: In order to have 100% no strings attached sex with as little drama as possible, he had to skew very, very young. We’re talking early 20s, here, girls right out of college who wanted to have fun and then move on to the next casual fuck.

He knew the odds were not in his favor, though. After all, he was turning 40 soon. Would a 23 year old really want to fuck a 40 year old? He decided honesty was the best policy, and so he crafted his bio to say that he was looking for something very casual and wanted to have fun.

CREAMPIE ANGST [mf] [mF] [oral] [mast] [swallow] [milf] [anal] [creampie] [creampie eating]

My ex knew I didn’t want kids, and yet, she tried to get pregnant time after time. Things got so bad that I developed a severe case of sex related erectile dysfunction. I didn’t want to have sex, and this was my body’s get out of jail free card. My ex couldn’t get pregnant if I couldn’t get hard.

Naturally, we broke up a short while after. But my anxiety followed me. Shortly after the breakup, I decided to go online and find some fun. I figured the best way to get over someone was to get under someone else. I hooked up with this skinny blonde with perky tits and a firm muscular ass. She was absolutely cute and adorable, but when her clothes were off and she was fidgeting and biting her bottom lip, her hair over her eyes, I couldn’t perform.

[MF] my unknown viagra encounter – more than expected – she spiked me

So, bear with me as I detail the recent “viagra adventure” and the backstory… sorry for the length, but it’s how it happened…

Let’s take care of a few things off the bat – I’m 38 / never had a problem getting it up, but have had the usual times we as males get after drinking / mental nerves on first encounters etc. All standard stuff, never felt the need for a pill like viagra (Sildenafil) never intended to take one…

However, I have a scandalous FWB that visits sometimes. She is slightly older, 44, mother of 2 – married to someone close to her age. She’s very fit, body that most 20 year olds would die for, and she somehow kept whatever form to her chest that childbirth gave her – ample / full / wonderfully huge nipples… and to top it off, she found out recently she has a wild side – and that’s me!

We have played games with each other in the past, when she started sleeping with me, we got a bit more adventurous and aggressive in the bedroom / torturing each-other at times. I took it up a notch when I had her rope-restrained as she requested, and she was playfully misbehaving, undoing her restraints and clawing at me… leaving some marks.

My Fiance’s Birthday Surprise Pt. 1 (Oral, Anal, Long) [FM]

~The Backstory~ 

I’ve been with my fiance for four years. He and I are incredibly sexually compatible and this year, I decided to surprise him with a secret trip to New Orleans complete with a night out to an expensive dinner, gambling at the casino, and a night of anal play at our Air BNB ;) Since we’ve been together for a good while, I had to really try to outdo last year’s birthday surprise that I had for him. I decided to buy a sexy lace bra and crotchless panty set that included a matching garter belt with clasps, lace stockings, anal lube, and a three set of butt plugs especially for the occasion. This is part 1 of the story of how I made SEVERAL of my man’s fantasies come true in just one night.

Part 1: Getting Ready

New Orleans was only a 4 hour drive away from where we were. I told him we were going to go to brunch then see a movie. I had packed a travel bag for him and hid it in the trunk, we went to brunch, and then I started driving East on the interstate. It took him a solid 20 minutes to realize we were not going to the movies. I handed him his “lucky tie” (the only one he gambles with) and he knew. 

How I started paying for my girlfriend to go to orgies [MF] [MF] [MF]

My girlfriend and and I started dating in college, years ago. We had a fun, if vanilla, sex life. The most daring thing that happened was that I bought her her first few thongs. She knew I liked it when she wore them during sex, so she would do that. The sex was frequent and enthusiastic, and I was happy. I graduated, and she still had a few years left. Since I was living a plane ride away, she brought up an open relationship, and I agreed. I had some fun during the open relationship, but that’s another story. Our open relationship had a few ground rules: use protection, don’t get emotionally attached, and a general “don’t ask, don’t tell” when it comes to hook up details, as she didn’t want to he about what I was up to. We talked a lot about feelings, reassured each other we still loved each other, talked on the phone all the time, had some phone sex, etc. I didn’t think very much about the open relationship at all; it was just a normal distance relationship.