Update — Been a lot going on

Country Girl

Yep its done and over with. I never did reply to her long text. There’s really no coming back from where she went.

Sugaring lesson here girls… If you don’t want to feel like a whore, don’t act like one.

Sugaring lesson here guys… If you dont want to feel like a “john” don’t make arrangements with girls that think of themselves as sex workers.

Smart Girl

We have committed to a year of arrangement. This happened when she asked me to co-sign for her apartment lease of a year. She has agreed that once her work schedule allows she will be meeting three times a week going forward. We are more or less doing that now.

Sex has been a bit of a challenge of late. Her schedule hasn’t allowed for more than an hour give or take to spend per meeting. She has this slow blow job technique that while not the best I’ve ever had, is definitely the sneakiest I’ve ever had. It takes a bit longer to get hard, but if I’m not paying close attention, it goes from hard to cuming in her mouth in just a couple of minutes.

Cuteness to be had!

So I asked her early on what she thought about when she masturbated. She was too shy to tell me. Of course I poked and probed the subject of her fantasies coming up with nothing. Then last week I brought up that I would spank the living shit out of her if did poorly in school this semester. BINGO! Despite her objections there was a sparkle in her eyes that just screamed SPANK ME!

Wednesday after her glass of water downed (I call her my favorite two hump camel), smoked her cig and went to the bathroom she came out to find me sitting in a straight back chair with no arms on it.

Wash your hands and come here.

She did. As she stood in front of me she asked what the chair was for. I was silent.  I reached up under her dress and grabbed the crouch of her panties and pulled her closer and then yanked them to the floor. I shoved a finger in her pussy and guided her to the side of the chair with it. She was already very wet… I up eneded her onto my lap and pulled her dress way up.

I rubbed her butt and legs for a short bit, then slid my hand between her legs and spread them. I grabbed a handful of hair and pulled her head back with my left hand while at the same time delivering a solid swat to her ass cheek with my right hand. There was a sharp intake of air and a squinting of her eyes. And it started…

On a scale of 1 – 10, she got somewhere between a 3 -5 hardness. I stopped after 15-20 swats as the redness was coming up nicely and played with her clit. She came like a good girl in a very short period of time, like maybe a minute or two at the most.

Back to spanking! Another 15-20 swats then stop to rub her clit, she came in seconds this time. Back to spanking and she came again just as I was about to stop to play with clit again, so I kept going. It took another 10-15 swats and she came again.

I spun her on my lap so I was holding her, her face of soaked in tears, red as a beet. Lower lip quivering which just begged for kissing. She didn’t want a lot of after care, she was hungry for cock and was off my lap and on her knees in a minutes times. She got me hard as a rock quickly and I pounded her in the chair doggy style for a good half an hour.

Afterwards in a nice cuddle… Yes this is more or LESS her fantasy. I explained how hard she was spanked and more in general about spanking. I explained that a truly hard spanking especially with a belt or cane or paddle would leave welts and marks for weeks, that she wouldn’t be able to sit without pain for days. Then I reinforced my “threat” to spank the living shit out of her if she didn’t do well this semester to which in the smallest of shy voice comes…

But what if that’s what I want?

She will be introduced to my black leather with spring steel insert paddle tomorrow…

How did I end up here?!?!

Smart Girl, great, very happy. Still looking for a real relationship though and find potentials in the form of arrangements.

The Chef

She is 19 and curvy. Okay while I like that SA added this as a body type, I hate to say its rather abused. Now my Chef is not an abuser! She is the text book definition of curvy. She is 5’6″ and IDK how many pounds. She has moderately firm DDD/E breasts with always hard up turned nipples. I’m kind of guessing here using what I know so bare with… In a mens pant size she is likely about a 45 waist. She has a firm round and big ass. Large muscular legs and flat tummy. You can “pinch and inch” most places on her, but make no mistake, this girl is fit as fit gets!

Long light brown to blond hair below her shoulders in length. The most beautiful green eyes I have ever seen and the face of an angel. With a smile that says nothing but wonderful.

She is primarily motivated by experience with an older man, a friend and mentor. Her request for allowance is VERY low, lower than if I were to use a backpage whore.

I’ve talked about “tight pussy” on the blog before. Basically there are two type of tight, one of natural tightness aka thick vaginal walls and the true tightness which is strong pelvic floor muscles.

The Chef is the tightest girl I’ve ever known! In both meanings. Despite her being dripping wet, it is an effort to penetrate her. When she squeezes OMG! She can literally stop a stroke and there is no movement unless she relaxes.

The sub

So I have a proper submissive now too. Just as with the Chef, her allowance is VERY low.

She is a true submissive with experience in the role. She chased me on SA for nearly a month before I finally gave in and agreed to “at least her for lunch”. Her pictures are not very attractive…

But she herself is a fucking knock out! Very smart, I’m guessing she has an IQ in the 130+ range. She’s never been measured. Polite, common interests in and out of bed. BINGO!

She is 5’6″ with a truly average build, a little extra weight around the hips, but nicely formed and will make a nice handle for pounding. Small perking and pierced breasts. We have our first private meeting Monday, so the rest is yet to be seen. She smells incredible!

She is into impact play, forced orgasms, sex in risky places.

If things work out well, she will be moving in when her lease is up early next year. She loves the idea of being kept in a domestic and sexual slave type relationship while in the home. She has somewhere between a 1950’s housewife and naked sex slave wish. We are both agreed that if this works out over time that a permanent relationship is likely to be the end result, aka marriage.

So here’s to a way too early to tell hope that I have found her!

One man's experiences in sugar dating