I guess this may qualify as a gangbang, LOL
Substitute Stripper (first Gang Bang)
As you can tell from our many stories we try to live out our fantasies. One of Elaine's was to be a stripper at a bachelor party. I was about to decide that would never happen as she was get older and did not know where we would ever find the right situations. Back then Elaine was about 45 and still semi hot. Some old friends and I were having a “bachelor party” for Dan, a guy we’ve known since about seventh grade and one of the last single, never-married, and straight guys around. Since we’re all in our forties, the bachelor party was pretty lame. Afternoon at Rick’s house, good beer, and college basketball. Nothing wrong, but not much of a party. We did have a stripper lined up as a surprise for Dan, but even that seemed like just a formality for the party and the agreement Rick made with her was pretty tame, just tits, maybe a peek under the g-string, a little nipple play for Dan and that seemed fine.
As time went by, and the beer loosened us up a bit, the thought of a college girl’s tits in Rick’s living room seemed more interesting. She showed up just a few minutes late, but there was a problem. Apparently her boyfriend, who was waiting in the car, had developed a problem with his girl stripping privately for other guys. Rick was talking with her, semi-privately, in the kitchen. She was a nice looking girl, kind of petite, great ass in her jeans and very big tits that her t-shirt couldn’t control. She was really sorry but she couldn’t go through with it so she was returning the money Rick had given her up front.
At this point I had an idea that I had to try. I stepped out on the patio and called Elaine. As I explained the situation she figured out where I was going and immediately gave a “you can’t be serious” answer. But I was serious, so I kept trying to convince her what a great chance this was to fulfill her fantasy of stripping. She made me go through the list of who was there, twice, then went silent. Finally she said, “check back with me in ten minutes…I have to think by myself”. I figured there was less than a 50 percent chance of her going through with it but my cock started to throb in my shorts at the possibility.
I ran the idea past Rick while I was waiting and, after he picked his jaw up off the floor he said he’d much rather see Elaine strip than our young stripper. In fact he was really excited . I held my breath as I called her back. I listened to her silence again for a few seconds, then she asked if we could somehow get one of the guys, Dave, to leave. She works with his wife and didn’t think he’d keep things to himself, and she was probably right. If we could do that she would come over. I quietly spread the news around to the guys, not telling them the new stripper would be Elaine and they agreed to pretend they were ready to leave. Dave isn’t much into parties and at the suggestion he was the first out the door.
I called Elaine back, and it seemed she was getting warmed up to the idea. She asked what she had to do and I told her to just wear something sexy and take it off slowly. She caught me off guard when she asked “Well, am I supposed to suck Dan’s cock? I thought the guy getting married usually got something special”. Wow! I told her it was definitely up to her but it sounded incredibly hot. She had always thought Dan was good-looking. Then she said, “Ok, I’ll be there in an hour and a half” and hung up. Could we wait that long?
An hour and a half later the doorbell rang. I answered the door and understood immediately the reason for the wait. Elaine was seriously dressed up. Her black dress, the one that I had only seen once at a formal party, clung to her and accentuated her beautiful, body. The long slit up the back revealed legs in sheer black stockings and sexy heels, extra makeup, and some unusual jewelry added just a hint of slut. We shared a long wet kiss I groped her ass for a second then led her down the hallway to the living room.
The guys went silent when they recognized her and there was nothing but the sound of the tv basketball game in the room. A couple mumbled “Hi Elaine” and she just grinned and took in the scene. She walked to the TV, bent over farther than she had to, ass very high and plenty of leg showing and turned it off. She pulled a CD out of her purse and asked Rick to put it on. As slow, sultry jazz filled the room Elaine moved slowly around, gently pushing the guys onto chairs or couches. Elaine isn’t the kind of woman you would expect to strip on a pole, but she was taking charge of the room in her own way.
She gently moved her back side in front of me and, from years of experience, I knew to slide her dress zipper down. Very slowly she moved to the middle of the room and worked the snug dress down. She turned to give me a shot of a new piece of lingerie; a black bra with the French-cut cups that just lifted her tits, leaving her nipples exposed. I assumed she had run out to by it for this occasion. She turned to let all the guys take this in while she slowly worked the dress lower. As her waist came into view, I was pleased to see her lacy black garter belt, and as the dress slipped to the floor, there was nothing more than stockings and heels. She seemed to shiver a little with excitement as the guys admired her bare ass and the pretty triangle patch of hair between her legs
