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My first gangbang..........try  

timelessoul 59M
1 posts
5/19/2011 4:56 pm
My first gangbang..........try


Like so many average guys out there I always liked the idea of having threesomes and gang bangs with women. I had seen plenty of porn depicting that kind of behavior and I wanted to try it. But convince my long term older girlfriend into having sex with me and another guy? Not likely my friend. Find another couple who wanted another guy, and not a girl? Hard to do, most wanted another lady. They might want you to be bi. Not my cup of tea. Or if they wanted a guy he had to have a washboard stomach and a 10 inch cock…..oh and be hot to. This is where I was really lacking. Closing in on 40, thinning hair, very average looks and a very average cock. My chances were slim. I had gotten to think that all that porn was bullshit, all paid actors and actresses doing all that stuff for the camera. Regular people did not have super hot sex like they do in the porn’s. Women having several penises in their pusses, asses and mouth all at the same time. Guys fucking great looking women, shooting cum in their faces. Did normal people have that kind of fun…
Well I had a lot fun finding out that I was wrong, way wrong. Let me tell you of my adventures. How I convinced more then 40 women that they could trust me to plan and stage gang bangs for them. I have staged over 60 GB’s and attended 30 or 40 more. I have sexual adventures that I thought only happened to the super good looking or paid porn actors. If you saw me on the street you would never imagine me to be the type of person who had porn style sex, with soccer moms, secretaries, clerks, nurses, business owners and yes, porn stars.

How it all started

I was watching the beautiful naked girl straddle one guy and lean forward so that the other guy could have access to her ass while the other guys saw sawing his cock in and out of her pussy. He got his cock firm up her ass and the lady started to howl with both a cock in her pussy and another in her ass at the same time. Another guy got his dick close to her face and she wrapped her lips around his dick and you heard the call of “She is Airtight” That went on for awhile then on guy shot his cum on her face. The other guy pulled out of her ass and shot his cum and her back and ass crack. By then I was yanking furiously on my cock and jacking off on my belly as the cum erupted from my cock. I turned off the VCR. Leaning back, wiping my semen up I again wondered if I would ever get to have a sexual encounter like the one I just saw. Damn, I really wanted to double penetrate a lady just once in my life. Most guys liked the idea or could only handle the idea of a threesome if there were two ladies. But I liked the idea of two or more guys just taking turns fucking the hell out of one woman. But where could I find one like that? I had replied to sex ads, but never with any success. Tried the local alternative papers but they seemed to be mostly, if not all fake ads. How could I break in and find that opportunity? I did not want to involve one of my real friends, or even let them know I was interested in that kind of sex. They might think I am gay or weird.
At this time in my life two things changed that might have had a very big impact on what I wanted to do. I have had laser surgery on my eyes and I no longer wore coke bottle thick glasses. It really had the effect of making me look very nerdy. Throw in a slight pot belly, so so looks and your basic six inch dick I did not have much to offer someone who wanted to have casual sex. Typically you would think they wanted the best eye candy they could get. That is how the ads seemed to run. But I also got a computer and the internet was opened up to me and millions of other people who might share my particular interest.
This is what I thought to do. Seeing ads there were women who stated they liked to be gang banged or have multiple men for sex. I thought why not advertise and answer ads for women who wanted to have GB’s and tell them I could supply the guys and the hotel. All they had to do was show up and have a good time. I figured I could gets lots of guys to show up. I answered several ads. Then one day a lady responded back, and it changed my sexual life from that point forward.

Got milk?

That was the headline to her ad. Got milk? What the hell did that mean? There was a photo with her ad but it was very fuzzy and showed a bigger looking woman wearing shorts. I had a rush of adrenaline, Wow I got a response! She had included a phone number. Nervous as a blushing bride and I tried to prepare myself to call and talk about her gang bang. I had no idea how to approach her over the phone, but I figured I would tell her that I knew a few guys . What else to say I do not know. I was going to wing it. Her name was Peggy.
I called and a female voice answered. I remember feeling very awkward a first. “Hi is this Peggy?” Yes it was. I started some small talk. Where was she located? Corona. Damn that was far away. It turned out she had no car and was living on a friends couch for the time being. She was Divorced, or separated. She had never had a GB, but she wanted to try. She was into some mild BDSM, liked toys and nasty conversation. She was open to all kinds of sex, including anal sex. She liked giving oral to completion and you could cum in her face. I could feel myself getting aroused from our conversation. Women who took cock up the ass were rare, I felt. Sure I had done a few there but not many. She had a motel she wanted to go to. It was cheap (all motels are cheap in Corona) and it had a Jacuzzi in the room. It sounded way cool to me. She wanted 5 or 6 guys. We agreed to that Saturday, about four day always. So we agreed to a GB and a day and time. I hung up the phone. Well I had my first live one. Now I had to find some guys. No problem I thought. There had to be lots and lots of guys I could get from the internet. Just put out an ad and gather up a few guys and let’s go fuck Peggy got milk?
What I did was put an ad in personals (it was free back then) for guys who wanted to GB women. It was an ad for the guys to be specifically with Peggy. She was open to race, which not all women are. I got about 6 or 7 guys to show interest, one claimed to be a Dr. I remember him emailing me, that you cannot believe how much pussy there is on the internet. I choose about 5 of the guys. Peggy told me she was going to have a few of her “friends” come over to. So we were looking at about 7 or 8 guys and her. As the week was ending I was getting very nervous. Would she show up? Can I get my dick hard in front of a bunch of guys? Is there going to be any gay stuff with so many guys? What does this lady really look like? Will I catch some venereal disease with all these strange guys and this woman who I know nothing about? The truth is I have only had sex with a stranger once…I was picked up outside of a Casino by this black lady who was claiming she needed a ride home. But that is another story, not this one. So could I perform with a lady who I had never met before? Sure I am guy but up to this point I had never done anything like this. Would I get freaked out with other naked guys in the room. How are we going to take turns? All sorts of questions were going through my mind before the day of the bang.
The time was 4pm and told them I would meet them in the parking lot or leave the room number in my car windshield. With incredible trepidation I drove the 50 miles plus to Corona. What the hell was I getting myself into? I brought condoms, lube and took a few sex toys with me. Well it was time to see if this was something I wanted. I pulled up to the motel parking lot; it was off a main street of Corona. For those of you unfamiliar with Corona it is a hot desert area known for cheap housing and certain unsavory elements. It is not a Palm Springs by far. Peggy had mentioned that she would get the room .
She was standing on the walk way conversing with some slinky looking . Peggy was short and fat. What we euphemistically refer to as BBW (Big Beautiful Woman) Even though we had not met, we both knew each other when you saw each other. It was a look of recognition I have noticed many times after. You are looking for someone who is looking for you. We greet each other and we go to the room. As advertised it had a Jacuzzi. That was a first to me and I was looking forward to trying it out.
We both smiled at each other, I was nervous and hardly knew where to start a conversation. After the small talk Peggy was telling me she invited a few of her friends (fuck buddies) but that they have not called back, I told her that I expected 4 guys on my end. She started to tell me about her sex life before her divorce. I took a hard physical look at her. I already saw she was like 5’2” and 220 plus pounds. Short mousy brown hair, it looked like it had been hacked in a fit of rage. When I looked in her eyes I wanted to shudder. The last time I had seen eyes like that I had worked in a locked psychiatric ward. Outside of a big set of tits there was little else to like on a physical level. She was nice and friendly in a simple slightly off sort of way.
I told her I had to see if any guys were waiting outside, and to leave the room number in the windshield. I had noticed it was about 15 after four. The guys should start showing up. Nobody was waiting in the parking lot. This was before I had a cell phone, so no way to know if they were running late or showing up at all. I went back to the room and listened to Peggy’s story.
She had married an older man who verbally abused and belittled her. They had never consummated the marriage. Horribly overweight, suffering from very low self esteem her life was miserable. After about 7 or 8 years of that crap she found a guy who wanted her, and despite the fact the old man scared the shit out of her she let the guy have sex with her. It was so wonderful for her, the second time she and the guy had sex underneath her husband’s window. She claimed they deliberately had loud sex so she would piss him off. Well that had worked just fine and he kicked her out and she since had explored her sexual side, abet at the expense of a secure home situation.
I looked at the clock; it was after 4:30. No one had shown up and I was getting a funny feeling nobody was. “I do not know where the guys are” I mentioned. It was looking bad. “Yeah I don’t know were Louie and Joe are” Peggy added. “Let’s try out the Jacuzzi” Why not I thought. We both took off out clothes. As she took off her top Peggy brightly said “Can you believe I lost 160 pounds?” With a frozen smile on my face I said you look great, but I was thinking it did not show! This lady was BIG. Her stomach still hung over her crotch. We got in the water, and she looked better with her big titties floating in the water.
Here we were. My guys aren’t showing up. Her fuck buddies have not shown up. I am sitting in a Jacuzzi with the fattest woman I have ever been with naked. What else is there to do? I lean over and start kissing her. I grab those monster breasts and start fondling her nipples. My cock is getting hard and she is responding to the kissing with little moans and aggressively kissing me back. From our conversations I know she is submissive mined and those women always like being lead and told what to do. I stand up and present my hard cock to her mouth and she gobbles it up nicely, like the hungry bitch that she is. Now I have since learned a few things about fat ladies, but they nearly to the woman suck and deep throat any reasonable sized man. Peggy was sucking a mean cock and licking the water off my balls. I lifted those massive tits out of the water a little and started to give her bit of a titty fucking. Since she was wet it my dick slid nicely between her breasts, and I would trust up so she could lick and suck on my dickhead. We got out of the Jacuzzi and dried off and went to the bed. Still no one was knocking at the door, and I had resigned myself to a solo adventure with Peggy, and so had she with me.
Her pussy was sopping wet, but really going down on her was not too fun. Fat belly and thighs, stretch marks galore it was more of a chore. I slipped on a condom and started to fuck her in the missionary position. That big belly was a turn off so I turned her over and started to do her doggy style. She liked her ass getting slapped and being verbally abused. So I gave it to her.
“You nasty slutty bitch you like have strangers fuck you”
“Come on you cum dump, fuck my cock harder” I keep smacking her ass, and using the natural lubrication from her pussy I was working my fingers up her ass.
“You fucking , you nasty piece of shit. You gonna let a total stranger fuck you in the ass? Pulling my cock out of her pussy I ripped the condom off and told her to “suck my dick” Again she enveloped my cock in her mouth “You slutty little bitch, you are going to do anything I say aren’t you? Here suck this cock” I thrust roughly into her mouth and head her head firmly, all the while saying anything nasty I could think of. Then I squatted over her mouth and let her lick my asshole” Clean it up bitch, make my asshole wet.” Really this was hot nasty sex with a woman I would not normally give a second glance to. But she was turned on, enjoyed everything we were doing and so was I. Next on the menu was her big fat ass. I lubed her up and slipped my penis in her ass no problem (I certainly was not the first one there). After awhile I stopped with the verbal abuse, I was tired of talking and was enjoying butt fucking her. She looked around, and in no uncertain terms told me” Keep talking, don’t stop talking!” That was basically the only thing she asked me to do. Keep up the nasty talk.
Two other things happened that day that still stick out in my mind. Both were first for me. At one point I had more then half of a 12 inch dildo up her ass and my cock at the same time. It was tight as hell and she was just moaning in pleasure away. Really I had my way with her anyway I wanted. I remember pulling my dick out of her ass, ripping the condom off and Cumming in her face just like they do in the porno’s. Essentially the experience I was looking for. It was nasty, hardcore and I loved it. The other event was something that was the urban legend to me, or so I thought. Peggy had mentioned that she got really wet and could squirt. It really did not register with me. I had read about squirters, and seen porno’s that were obvious fakes of women squirting. I just did not really think a woman could ejaculate like a man. At some point during the sexual encounter I was working the dildo in her ass and the vibrator in her pussy. She started grunting “Here it comes” and right before my eyes she squirted a massive amount of liquid over my hands and past my wrists. I could not believe what I just saw. I felt my hands and they were wet. The sheets were soaked. I reached up and smelt my hand and there was virtually no smell, tasted my finger and there was no taste. But it was like a watery lubricant similar to the natural fluids a woman produces. I was amazed! I got her to squirt a few times more, but nothing like that first time.
After a couple hours of sex and soaking in the Jacuzzi I was done. We both seemed sad no one else showed up, that was the point of the encounter. We had made the best of it. We hugged, and parted ways. I had a long trip back home, and despite the wonderful nasty sex with that less then attractive fat woman, I was bummed out and pissed off that the other guys had not shown up. That was my first lesson about guys from the internet. I also felt bad that I had promised Peggy and GB and 4 other guys and I did not deliver. Still I had not had my first threesome, foursome or more some. I did hook up with a woman, and without meeting her or dating her I had sex with her. That was new to me. Never been with<b> squirter </font></b>before, I had thought it was all fake before that. So this whole thing was not a total failure, only because I got laid. But the woman was sort of creepy and quite frankly, unattractive. I did not think I would be hooking up with Peggy again. I was even more determined to make this happen. I was going to get my gang bang.

rm_loveslilies 57F
36204 posts
6/7/2011 12:43 pm

I'm with voluptuous.

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