Ghetto thickness unmatched
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My experience with one particular dating site has been far less than stellar since I joined about six months ago. It's the six-letter one that starts with "T." Since I'm at the far upper end of the age spectrum (71), I can't imagine I'm a "hot commodity" for most women on there, although I sure attract my share of "fakes, flakes and foreign babes." Judging from my responses alone, there must be an entire section of Hong Kong bursting with gorgeous women anxious to hook up. Yeah -- right!
This past Friday night was the anomaly. At about 10 pm I was alerted to a match. Swiping right to accept, I saw that Emily was a 33-y/o Hispanic woman. I decided to cut to the chase and announce I was horny and looking for a meeting that very night. Since I was ready for bed, I figured it didn't cost me anything to pour on the pressure. Much to my surprise, she admitted a similar interest, and we soon came to a tentative agreement.
Since I'm married, I can't host, She claimed to have moved to Denver recently and had two roommates who were [a] home for the evening and [b] had friends over. She lived in a large apartment complex in one of Denver's north suburbs, so I suggested we meet at a 24/7 porn theater that turned out to be literally 20 blocks from her place. She was skittish about that prospect, so instead she suggested I drive over to the clubhouse area of her complex and we meet for some car play.
Ten minutes later, I was out the door and on my way. My wife and I share a 2BR condo, and one of its advantages is that our bedrooms are on opposite sides of the unit. On Friday nights, she takes a sleeping pill, so it's possible to slip out unnoticed. Emily messaged me twice as I headed north, clearly concerned that I might flake out on her. Thirty minutes after I pulled out of my garage, I was parked in front of her complex's clubhouse and promptly let her know I'd arrived.
She walked up to my car just as I was climbing out. She's about 5-5, 160 pounds, large tits, big butt, and a soft "poochy" belly. We kissed briefly but felt rather exposed under the parking lot lights, so we climbed into the backseat of my car from opposite sides. I drive a Prius, which is hardly conducive to amorous activity, but she was clearly horny enough to want to make this work. She wore a peach-colored mini-dress with thin shoulder straps and a scoop-neck front to show off her cleavage. We kissed some more while trying to find an optimal position for further action.
Reaching up under her dress, I quickly discovered she was naked beneath it, with a smooth hairless pussy that was already getting moist. She pulled down her top to give me access to her nipples -- nothing special, but sensitive -- and shifted into the corner of the backseat as she pulled the hem of her dress up to her waist. Even after she hooked her right ankle up over the front passenger seat to give me full access to her slit -- her thick thighs were spread as far apart as room would allow -- the area wasn't quite spacious enough for me to go down on her.
So instead, I proceeded to rub her pussy with my left hand while using my right hand to massage her tits and tug on her nipples. Over the course of about 20 minutes, I finger-fucked her to at least a dozen orgasms. At various points in the process I had two fingers in her vagina, three in, and four in -- pumping away like a madman as she rode the wave multiple times. I tried to fist her, but my hands are fairly large, so the best I could do was four fingers plus the thumb up to the first knuckle.
She was extremely vocal -- alternately urging me on and announcing each impending orgasm -- so it was a good thing I'd left my car windows closed. Four or five times she reached down with her right hand to brush-bate her clit as i worked my hand in and out of her pussy, and twice she grabbed hold of my t-shirt with her left hand and twisted the cloth (plus a bit of the underlying skin!) as she came. [When I got home, I saw there was a speck of blood in the center of my shirt.] At one point I administered The Shocker (three fingers in her pussy, plus my pinkie deep in her ass), and not only did she NOT object to the intrusion, but twice more in the throes of an orgasm she boldly invited me to do it again. "That's the first time I had someone do that to my ass," she claimed. I kind of doubted that, but I was in no mood to refute her claim.
Twice during our fingering session I took a slight break -- hey, I'm OLD! -- and withdrew my fingers to lick off her juices. The second time, I offered her the first taste, and she greedily sucked two of my fingers into her mouth.
Naturally I was hoping for some reciprocating action, but before I could shift in my seat and start to pull down my gym shorts, Emily said, "Geez, look at the time, My roommates will be wondering where I'd gone." With that she delicately lifted her ankle off the front seat where it'd been resting, climbed out of the car, and did a quick adjustment to her dress so that all the naughty bits were covered up.
I suggested a return engagement for Sunday afternoon, and she seemed quite enthusiastic to meet me at the porn theater a mere two miles from her apartment. Off she went into the night, and I headed home. When I got there, I pulled out my phone to message her about Sunday, only to discover she'd "unmatched" me in the interim. I caught myself thinking, "I bet she did that as I was driving away," and was pissed at myself for not having secured some other way to contact her. She'd gotten what she wanted without having to satisfy me, but I still had fun. "Her loss," I figured, since if we'd actually gotten together on Sunday in a place with room to stretch out, there would have been some serious pussy eating going on.
I had my first sexual experience pretty late, at 19, and it wasn't penetration, but just a hand job. I was a shy young man, and she was this 45 year old, smoking hot, neighbor's trophy wife.
She was always drunk, and in the party mood, my mom did hang out with her, but not so very often, and she would always call her names in private, when she thought I couldn't hear.
So, since they were "friends" I could use their pool whenever I wanted, so I took advantage of that opportunity as often as I could. Her husband was at least 20 years her senior, and never around, so I would just relax, and watch her around the pool - she was a kind of woman who would down a bottle of wine before noon.
She always wore tongue bikinis, and that was an eye full, which I used to satisfy myself, back home. Soon enough, I got braver and changed my saggy boxer swim suit, to the slip one, in an effort to reveal my erection, which was almost constant when she was around. She started noticing, and joking about it. Oh man, at that time, I would cut my visits short, just to get back home and release the tension.
One day, her kids (older than me) were home, and I felt kind of embarassed for the way I looked in those skinny shorts, almost ran away home, but they got out soon enough, to go to the city, and she was merrier than usual, and sat besides me. She, obviously had some thought about my "readiness" I presented each time, since, she flat out asked me "what I got there". Now, as a grown man, I would find something witty to answer, but at that time, I just froze. I swear to God, my heart was about to fail. She was drunk, and laughing, and started posing for me, turning her back to me, asking me if I "still like the old woman she is". Nothing, I was still mute. My hands were shaking, I thought she will shame me, talk to my mother, that my life is over, and that I will be known as a street pervert...
Instead of that, she got on her knees, and pulled my swim suit down, commented that "it is beautiful", and started to stroke me.
She was looking me in the eyes, than at my cock, than my eyes again. Her tits were swinging in the bikini, in front of me. Now I know, that if I touched her, she would, maybe, be ready for more, or that, if I pulled her head down, she would probably blow me. I did none of it, just gasped for air, shaking, and came after a few minutes, shooting three of the biggest ropes of cum, in my entire life.
I basically ran away afterwards, that is how confused I was.
The same night, my mom told me that she called, to let me know that they are emptying the pool for the season (it was still the begining of August). I guess, after sobering up, she realized that she went over the line with her friend's son.
After that, I went to college, and never attended her pool, again. Soon after, her looks deteriorated, but the few times I saw her, on the street, when visiting my folks, she would send me this naughty smile.
I have had more than a dozen of women after that, in a way, that was a catalyst for me to behave more freely around women, but till this day, this was the hottest thing I ever experienced, the mixture of surprise, innocence, fear and excitement, I felt that day, stayed unmatched in the following 20 years of my life.