mrbojangles on Collarspace

7/27/2010 9:23:46 PM

Ok, I've been active on this site for a couple months, I have met so many interesting, beautiful people so far and for some reason; I feel like sharing with you my craziest experience YTD. I know, I might get some flack for this, but it sure makes for a great story and I honestly don't know how I could be creative enough to think of this.

About six weeks ago, I was on the site on a Thursday night at about midnight and began talking to a forty-something lady who said she lived over an hour away from me. Now, it's difficult for me to explain, actually: it’s another topic; but for some reason: me and older women seem to click well. They tend to hit on me more than women my age or younger. Actually, I wouldn’t know what to say to a twenty-two year old. But the bottom line is I tend to draw older ladies, it’s the bottom line, and I enjoy it because I find maturity and intelligence a huge turn-on. Anyway, this woman was forty-something and for about two hours, we talked and flirted in chat.

So, at about two-thirty in the morning, she asked me if I would like to meet and offered to drive out to me. Yeah, I’ve only known this person for not even three hours and suddenly, things were becoming interesting and I sparked an interest. I mean, I’ve had my share of strange sex and within the last five years, I think I’m getting to the point of realizing it’s very much juvenile behavior and something about having sex with a stranger is just weird. I have to get to know her to some point and make the decision or offer to meet. But for some reason, I was feeling an interest in her offer to drive out in the dark. –Not so much horny I felt, but she seemed like a cool, free spirit and I was up for a rendez-vous thinking, "just how far can I take this?" Especially if she’s willing to drive a couple hours in the dead of the night. I thought it was sweet of her.

Another turn-on for me, as I admited to her in discussion is when women dress up and to some extent: role play. But I’m a sucker for girly things, lacey things, lingerie, heels, stockings, outfits, etc. What’s so important to note is the conversation I was having with this far away lady and she said she likes to dress up for her man and with the pictures she was sharing of her outfits, I was blown away. -Not really, but I could tell we had simmilar interests and that always makes me at ease meeting someon. However, something creative was brewing in my mind and I couldn’t resist pursuing a strange request that came to me and waited for the right moment. So I agreed to meet this stranger in the night and invited her over to my place. The following question she asked was, “What would you like me to wear for you?”

In the heat of the moment, I had to think. It's such a strange, dead hour of the night and if she’s coming all this way and take the time to pretty herself to my liking: I’m gonna make it worthwhile and then the idea came to me.

“Can you dress up like a realtor?” I asked.

After a pause, she replies, “Yes, but I work in the medical field so I have something that might work.”

Whatever the medical field business meant, I think it had to do with not having a designer business wardrobe, which makes sense because she was a lab tech at a hospital, and said she could find something to dress up as a real estate agent. So, her next question was she had to ask why and I told her.

“Well, how about you dress up as a realtor, show up with a briefcase and a stack of papers resembling flyers. Then, I will pretend I’m interested in buying my house and you pretend like you listed it and you’re showing it to me. I want you to give me a tour of my own house and try to sell it to me!”

Now, for almost four o’clock, I thought this was one of the funniest, craziest, soon-to-be most interesting encounter with someone from the internet. Besides, this lady even took her time at my request to primp and get ready to dress like a realtor to drive over an hour to a place she’s never been dressed up in business attire and thinking of her role: sell, baby! Give the homeowner a tour of his own place while he’s pretending to be interested and possibly buying it. Brilliant, comical, and highly erotic. I didn’t know what to think or expect. In every case meeting people, I never expect anything because I never know what I’m walking into or showing up.

By six a.m., my cell was ringing and she was minutes away. The dawn was breaking into a beautiful summer morning as she was pulling into my driveway and when I approached the vehicle, it looked like a car a real estate agent would drive and inside, driver side sat an attractive middle-aged lady who looked like a professional realtor. The inside of her car was even detailed and my first joke was asking her If she even had “Open House” signs in the trunk? Shit, with the government center and county jail a block away, my street and sidewalk gets busy early and stays that way all day. I even know a lot of the county workers because they walk by at the same time Monday through Friday. Ugg…and neighbors soon waking up. What the hell are people going to think?

Well, fuck it! Who cares what they think. I decided that if anyone saw me with this suited cougar, I would tell them I was with a real estate agent and I was thinking about buying the place. Duh!

Getting down to brass tax: she showed me my garage and talked about the space and heating efficiency. –Wrong, there’s no insulation or heat in there, but I could tell my realtor was already hot in the panties with certain eye contact and showing off her curves in fancy clothes. Next, we walked all over the yard and she showed me my garden and I asked her about the property line. Her reaction was bold and she pulled through with an answer I wouldn’t have guessed and I thought that was pretty hot as a display of intelligence. But deep down inside, as morning was moving along I was hoping people would see me and wonder what the fuck? I mean, I was so into this whole game I kept thinking how weird it was to have someone show a house at a strange hour. This lady was playing the role of a real estate agent to a tee and it wasn’t like she was dressed in Sunday clothes. I mean, she actually looked like someone you would see on an advertisement on a city bus stop bench and for neighbors to see this, I just love messing with people.

Our next stop, she took me inside and gave me a tour of my own home. We went through all the rooms, and I could tell she was getting flustered standing in my bedroom looking at my bed and in the bathrooms and kitchen, I made her bend over or sit on every countertop. She was really getting off on me checking her ass out. That to me was awesome because women really appreciate that stuff. ! When she showed me the washer and dryer, I had to ask if her panties were wet. And she embraced me, trying to make her move to sit herself on the washer and probably wanted me to have my way with her.

It was such a strange night, so badly I wanted to have sex and there was no doubt she wanted my cock. Instead, we got heavy and in almost every room of my house I made her cum with my mouth. For some reason, I wanted to make this woman cum over and over with my mouth and fingers. To me, it meant something because a female orgasm is exactly like a car accident: there’s a lot of noise and commotion and nobody has a fucking clue what just happened. Over and over, I made her pussy do things she never imagined. I mean, it’s fascinating to witness a female who’s beside herself with her pussy out-of-control like she’s never seen in all her life.

After about four hours of stroking her in every position imaginable, in every room, on top of every appliance, staircase, countertop, and furniture item: every room smelled not so much like healthy sex, but a nice clean pussy over worked and over played. For hours of rough pussy play, and hair pulling, sweating and all sorts of dirty talk , yelling and spanking. I gave this lady exactly what she wanted and that was to feel perma-fucked for the next week. Her clothes barley made her presentable and everything about her was both soaking wet and well trashed: her pussy, her makeup she spent all that time perfecting, her hair from all the pulling, a nice red ass. By the time we ended, and were relaxing, this woman looked to me as if she was a victim of something fucked up like King Kong fucked the living shit out of her. The only exception was her glowing smile and she was speechless with glee.

“There’s milk and cookies in the fridge, help yourself on the way out.” I said jokingly. So, we hung out and cooled down for quite a while, I asked about living out in the sticks, and she started talking about the housing market where she lives and how she bought her house (she may have forgot for a second the theme of the morning, but by this point, I was pretty sick of talking house especially if I’m not looking for one. By 11am, she was cleaned up quite well but when women have that freshly fucked feeling, they can’t hide it and I even told her she should stop at every Super America or Holiday gas station just to show off her glow. –She liked the idea and even showed me she still had a chunk of cum left in her hair from me giving her a Donald Trump.

In case you don’t know what that is, it’s when a guy deepthroats a chick like a maniac and right before he ejaculates, he pulls his cock out and shoots the load above her forehead and then smears the wad up into her hair so it sticks to one side like a comb-over (ie Donald Trump) and then slaps the female in the face and says, “You’re fired!” I never done that before, and never met a woman who was into so much twisted domination. I would never expect a middle age, professional, independent, woman to explain and ask me for these kinds of dirty favors. By the same token: I didn’t think I had it in me to be this creative and meet someone in such a wild, provocative, alluring, and creative way. I really hate taking risks, but sometimes doing something different teaches us something or gives us an enjoyable experience.