How and where to "entertain"?

#1
After years of searching for a non-pro for play, I finally found her.
Ever since I was a teen I've enjoyed bdsm. I started out as a masochist and found myself bottoming, mostly to pro-dommes over the years. I always enjoyed harder and harder play. As most of you know, sex with pros is usually not on the table, and that was fine. I was lucky enough to have some "personal slave" relationships when I was younger (and had more hair and was in better shape). Eventually came marriage and vanilla and kids and then hating the s/o and no sex what-so-ever. The lack of disposable income has put a stop to any type of play, along with not being able to hide transactions and my refusal to take money out of the family needs, despite my growing need for companionship or sex or kink.

I've been searching on OKC, Fet and some others, but mostly morbidly obese black female subs would contact me. Just not my thing. I'm too picky, and have too many neuroses - I admit it. Also, I won't put up any face pic or even share online because of my situation and my line of work. I eventually changed my dating site profile to a blatant bdsm one, but ambiguous as to whether dom or sub.

I open up a 26 year old cute chick (who has nothing kink related in her profile) but we are a near 100% match. After a week or so of messaging come to find out she's submissive. Like major. We start sexting and she's sending nudes. She's got roommates and I've got wife and kids at home. She's desperate to meet. I meet up with her one night in front of her place just to see if she's as real as she appears and holy shit- she is. She's hotter in person and a fucking slut. I'm fingering her in some shitty part of Brooklyn and I've got her against a wall as she's trying to get my dick out. She wants me to choke her and I oblige, but theres no way I'm getting put on the internet fucking a chick or getting blown- I calm her down and tell her I'm married. She doesn't care! She just wants it.

I tell her we'll figure out logistics and go home with blue balls. The next week is her non stop messaging me nudes, telling me how much she wants me and how she's getting fucked by other guys and what they do to her. Meet up again outside her job and again wants to pull her clothes off.

Neither can afford a hotel, I can't/won't show id, theres always a roommate home, I need to be able to shower off any possible signs of her before I get home and I won't bang her in public. (She's offered to fuck in bathrooms- gross!!!)

And oh yeah, she wants me to beat her and choke her and face fuck her, fuck her ass, fist her and more. So I've pretty much found the female version of me, and I can't fucking find a place to use her. Despite the fact that I've been looking for someone like her pretty much my whole life. And she really is hot.

As the kids say, "FML".

I've got an appointment next week with a dr. where I expect to get generic viagra, because there's no way in hell I'm not going to perform. (And I'm hoping for a 4 hour erection with her).
 
#5
Well, here's an update.
We met up twice since the original post. Drove around Brooklyn while I fingered her in the passenger seat and got her off a few times (I thought she lived near the industrial section- she doesn't, and I only had 45 minutes or so)(plus she was hungover from NYE and didn't want to upchuck all over my car by deepthroating). She constantly texts me how she needs me to be inside her and needs me to own her. Now, remember, I'm more of a sub - a perverted kinkster, but mostly a sub. The last time I played with a real sub was over 20 years ago.

I'm still strapped for cash so I took a recommendation that was made and found a Days Inn in Brooklyn that has hourly rates ($60 for 3 hours) and was going to take her there. And then last night I'm googling and find really nasty reviews of the place (bedbugs, stenches, thin walls etc.) and freak out. I need to be able to get into a zone of just having fun, not worrying that something is going to crawl up my leg. I found a bunch of "dayuse" hotels that, while more than I was hoping to spend, were legit hotels with great reviews and clean. I decided the added cost was worth it for both our sakes. I confirmed with her that she was ok putting it on her card and using her id to register so that I wouldn't get a letter in the mail thanking me for staying.

Yesterday I also got a script for generic viagra, 50mg and raced out to the pharmacy to pick it up. I wish I had known that 30 pills were only $50.00!! long ago! YES! I'm going to be able to keep it up when the condom goes on! Given this opportunity I don't need to blow it with a 26 year old!

She decides that she wants the room at a place that has availability at 8 this morning because she can't wait to fuck and get abused. I pop a viagra at 715 and get a hard on by 735 like I haven't felt in a long time. I'm thinking "this is going to work!"
 
#7
She checks in while I'm a couple of minutes away and texts me. Mind you, she has only ever referred to me as "Sir". This is obviously an important kink for her and I'm loving it. I rationalize it as I know how amazing submission is, how it gets my endorphins going, that I know what turn on pain is and if I can bring a woman those same feelings than, it's a turn on for me. I mean, sure, I'd prefer to be hung upside down and beaten, fisted and anally taken by massive objects, but let's get real- that doesn't happen unless you're paying big bucks for a professional to do it to you.

This is really happening! I meet her in the lobby, at 8:02, and at the elevator I whisper in her ear "If you have to pee or use the toilet, you ask permission- if I grant it, you will do it in front of me". She looks up at me, bites her lip and whispers back "yes Sir". Fuck...... In the elevator and immediately aggressive making out. In the room by 8:04, naked by 8:06 and eating her pussy by 8:09.

I can't believe its taken this long (I think we've been talking for 3-4 weeks) to finally get together, but holy shit, she is so fucking hot. I'm hard thankfully and tell her to suck my cock. SHe's mentioned she wants me to gag her on it and make her choke so....sure. (I soon find that, for me at least, the idea is better than actually doing it). I eat her ass, her pussy, I feed her her juice, choke her, smack her and she's moaning and screaming and loving it all. I'm on top of the world!

"I need you inside me Sir....please...." She told me earlier that she only fucks one guy without condoms and that I'd need to cover up. Which is also why I got the viagra. I also went and got tested a few days ago and came back neg for the big one and told her. I told her to pick up condoms and she brings out a giant box. At this point, I'm thinking ....please stay erect, please stay erect.....and I do. I put the rubber on and go to fuck her and.........FUCK! I go semi. FUCK!!

What's the one thing we men hate to hear from a woman?

"it's ok"


NO IT ISN'T FUCKING OK!

I go back to fingering her, eating her pussy, finger her ass etc. Try again. Same. FUCK!

As my mind goes to what she's going to tell the guy she's going to meet tonight about this older dude who couldn't keep hard, I try to not get into the self fulfilling mode of worrying about a hard on which, for me, only makes it more difficult to concentrate on the task at hand. So, I say out loud "fucking condoms". After a few more attempts I pull the rubber off and go back to manhandling her and bringing her to multiple orgasms.

As I start to rub my cock up and down her soaking pussy, she says "I really need you inside me....." "Please, put it inside me...." She sees there's no condom- shit she just sucked it......and I take the plunge. FUCK YES! Her pussy felt so fucking great.....

We fuck, I'm able to stick my full hand to the knuckles in her bringing her to an even bigger orgasm and just have a blast for the next 4-5 hours. I realize I'm starting to go soft again as I try to enter her ass repeatedly. Then she tells me she wants me to cum inside her. I haven't jerked off in 10+ days and I tell her what I'm going to make her do with the cum.
 
#8
Apparently 50mg viagra isn't enough for me...........every time I go soft I fuck her face. I get hard, can fuck her for a bit, but evrytie I go for her tight ass....caput. About 12 I tell her she needs to get me off. She tries like a champ. She notices that when I'm on top of her and she's touching my chest I get harder. "You did say you like pain" (Shit, if you only knew!) I show her that when she's got a hand on my groin I get harder. I realize it's the human touch I've been missing for years. It's not just errogenous zones, it's that I haven't been touched like this in fucking years and I'm fuckin around with someone half my age and it feels so damn good.

She tries like a champ- I cannot stop eating her pussy and paying attention to her. She sucks my balls and while painful at times, I'm moaning and loving it, even if it does make me semi soft for a few seconds from the pain. I can't cum. I FUCKING CAN"T CUM. Maybe its nerves; maybe its the viagra. Maybe it's ... I don't know but I wanted to..needed to cum.

There's so much making out and caressing- she's worn out and laying with her eyes closed. I go back to eating her pussy and more.

I left her ass bruised, her tits and cunt sore from abuse. Choked her repeatedly, gave her almost everything she sought.........

Took some nice pics of her gobbling my cock.

I covered the room expense.

Came home, showered and trued to j/o. Couldn't. I'm just fucked.

She texted me that the guy she's seeing tonight is going to be jealous of the bruising. I'm glad- but I'm pissed at myself for not being able to fuck her like I wanted- like she wanted.

I'll up the dose to 100mg and see how that works.

Oh, she mentioned to me a few days ago how she's got one SB arrangement (which is funny because I don't recall seeing her on SA (I've got the free version)). I really like this whore.
 
#9
Sooooo.........

After that first time there was constant sexting- and requests for me to meet her during lunch or after work. She'd text me in graphic detail her dates with other guys and about how they used her. Nothing was or is off limits with her.

We met up again at the same hotel. On the way over, I popped 100mg of Viagra this time....and holy shit......within 15 minutes it was like I had the cock of a 17 year old! She texts me that she's left the room door ajar and that she has a butt plug in. BOING!! I get there, and I find her just like that. She starts to rip my clothes off and I start to fuck her straight away. There's no going soft, there's no erection problems at all! We go at it for 6 hours. I've never skull fucked a woman before and didn't think I'd get into it, but damn, I did! My cock was glistening with all her spit and mucous at one point, I just pulled threw her down and rammed it in her soaking cunt.......
Her ass was extremely tight and while I didn't really go soft every time I tried to fuck it, I was able to get it in once- even with lube...I guess my head is just too big. Next time I'll focus on that ass.

She was throughly used and at a few points was too sore and too wasted to go on. Some cuddling and care took care of that. I wasn't able to cum (wondering if it's the viagra or just my brain) but that I'll work on too.

Met up multiple times afterwards for takeouts near her job, and then makeup and bj in car- I'm not super comfortable with the public bj so that was my issue. I haven't j/o in 3 weeks in an attempt to desensitize my self to porn j/o.

I've followed this board for years, envious of mongers. I'm glad I can contribute something.
 
#10
Where, in Manhattan, can one safely engage in getting a quickky bj or fucking without getting busted? I dislike playing in the car. Read that there's a gay bar, The Cock, in the east village with a basement where guys go to have sex, but I don't know how they'd take to a heater couple coming in. (Also, looking for either free admission, low cover and or not having to go to a swingers club late night). You know, like during the day or evening........
 
#11
Where, in Manhattan, can one safely engage in getting a quickky bj or fucking without getting busted? I dislike playing in the car. Read that there's a gay bar, The Cock, in the east village with a basement where guys go to have sex, but I don't know how they'd take to a heater couple coming in. (Also, looking for either free admission, low cover and or not having to go to a swingers club late night). You know, like during the day or evening........
Love the screenname
 

Slinky Bender

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#12
Where, in Manhattan, can one safely engage in getting a quickky bj or fucking without getting busted? I dislike playing in the car. Read that there's a gay bar, The Cock, in the east village with a basement where guys go to have sex, but I don't know how they'd take to a heater couple coming in. (Also, looking for either free admission, low cover and or not having to go to a swingers club late night). You know, like during the day or evening........
That was the location of my last party when the place was still Lit.
 
#13
Where, in Manhattan, can one safely engage in getting a quickky bj or fucking without getting busted? I dislike playing in the car. Read that there's a gay bar, The Cock, in the east village with a basement where guys go to have sex, but I don't know how they'd take to a heater couple coming in. (Also, looking for either free admission, low cover and or not having to go to a swingers club late night). You know, like during the day or evening........
I have seen posts in the events section on Fetlife for swinger clubs that have daytime stuff. I may have used the hotel lobby restaurant unisex bathroom at a place near the Highline and 14th street.
 
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