Brown Bagging It


Caution: This Sex Story contains strong sexual content, including Heterosexual, Safe Sex, Oral Sex, Anal Sex, Masturbation, Petting, Sex Toys, .

Desc: Sex Story: Jack and Steve end up brown-bagging it together

"You can't be serious," I told Jack. "Where the hell did you hear about this anyway?"

Jack was my best friend, had been for years. He'd been the high school basketball star, moved on and did well in college though he'd opted for a job in marketing where his good looks, charm and bright white smile made him a favorite amongst the ladies.

"A friend of a friend," he said simply. Yeah sure, I'd heard those stories before.

"Well I don't believe it," I told him. "No star, no icon would go out and purposely do something like this, and even if as you say, no one knows who she is, what's the point?"

"The point my friend," Jack began, "Is that you get a chance to do anything you want to with her, you have the knowledge that it IS someone famous, even if you don't know, or are not sure if she really is who she claims to be. The fact is, it's possible, maybe it really is someone famous. But the bottom line, it's a free-fuck with obviously a good looking woman with a hell of a lot of money, so what's to lose?"

He had a point there, but I was still leery of the whole thing. "O.k., so how's this work?" I asked. Jack was grinning now.

"So you are interested then?"

"We'll see," I said simply. "After I hear a bit more."

The marketing firm Jack worked for had a list of some pretty prestigious clients, one of these had told one of the V.P.'s of the firm about an experience he'd had, and had sworn by it that it was true. The client had even gone so far as to give Mark, the Executive V.P. the email address to contact, and the code that went along with it.

"So then what?" I asked.

Jack laughed, "Steve, your hard-on's showing, I knew you'd be interested!"

I actually did have one as I sat there thinking about it, but I knew he was only referring to my frame of mind and not my actual condition as he'd had to have been looking beneath the table to know that I did.

"Like I said Jack, then what?"

"You email them the code, along with three photo's, one a full face photo, the second a full body photo but distinct enough to know that it's still you, and finally, a fully nude photo of yourself in an aroused state."

I shook my head, "You're kidding me."

"Nope! That's what Mark told me he had to do when he went."

"So he really went, and she, whoever it really was, or wasn't, was actually lying there in bed, naked, with a brown paper sack over her head."

"Yeah, she was. I know it sounds weird..."

"Sounds weird? Fuck Jack, it IS weird!"

"Regardless, Mark said he had the time of his life, and that she had an obsofuckinglutely gorgeous body."

"And he went with this client friend of his."

"Yep, I guess she prefers it when it's two guys at a time, if not three."

I thought about that, I could handle doing something like this with Jack easily, we'd actually fucked a pair of sister's in the same room before and had even switched partners, so doing something like this with him was no big deal, even though Jack's monster sized prick made my average sized one puny in comparison.

"So after we send off the photos, then what?"

"We wait to see if we've been accepted. If we are, then we get another email giving us a time and place to be. We show up, a limo arrives to meet us, we're then blind-folded and taken to her home as I understand it."

"Holy shit!"

"Yeah, that's what I said!"

Nearly a month had gone by since Jack and I had submitted our photos to the anonymous email address. So far we hadn't heard a thing and I was beginning to think that it was either a poorly conceived practical joke on us, or that we'd actually been rejected.

I had heard the "ding" on my computer informing me that I had mail, I opened it and read:

"Be at David Letterman's star on the Hollywood walk of fame Friday night 8:00 sharp. You'll have a five minute window, don't be late."

I read the message again. "You've got to be kidding me!" I thought, just as the phone rang.


"You just get what I got?" Jack asked.

"Yeah, what's up with that?"

I heard Jack laughing. "That's the other thing Mark told me about, apparently whoever this woman is, she's appeared on his show a number of times, sort of has a thing for him as I understand it, whoever she is."

I realized after this, I'd have to start watching his show a hell of a lot more often.

"Well that sort of makes it a bit more interesting doesn't it?" I had to admit. "So ... we're going?"

"Hell, why not?" Jack said.

There was an address where we could of course find Letterman's star, though I drove down at noon to make sure I knew exactly where it was. On Friday, Jack and I arrived fifteen minutes early, feeling a bit foolish as we stood there waiting for a limo to pull up along side us.

"This could still be someone's idea of a practical joke," I told Jack. "We could be on camera right now with someone laughing their asses off at a pair of idiots who actually believe they're soon going to be fucking some famous woman."

"Nah ... I think this is legit," Jack stated smiling. "Here comes the limo now!"

He was right of course, I watched as the limo turned the corner, then pulled towards the curb stopping where we were standing, though no one got out to meet us or even acknowledge that we were even there. Jack was the bold one, finally reaching for and opening the door. I stood there watching. "Well? You coming with me?" He grinned. I quickly slid onto the seat beside him, closing the door.

The panel separating the driver's area from where we were was up. The lights stayed on for a moment longer, and then went off. Almost immediately after that the car pulled away from the curb and began moving again.

"Gentlemen? You'll find a pair of black masks located in the small box in front of you. When I tell you to put them on, please do so. Until then, you're invited to enjoy a drink from the fully stocked bar if you'd like. I'll now be darkening the windows so that you can no longer see where it is we're going, as well as locking the doors. If at any time you wish to leave the limo, please say so before our arrival and we'll return you back to where we picked you up. Any questions?"

"Ah ... no," Jack answered for us both. "Thank you," though neither of us heard any further response.

"Well? What would you like to drink?" Jack asked grinning from ear to ear.

After about twenty minutes we heard the anonymous voice speak to us once again. "Please finish your drinks gentlemen, and then place your blindfolds on. We'll be arriving at our destination shortly. Once we have done so, remain seated. Someone will open the door and help you step out. You will then feel an additional head covering placed over you, you will be led from the car into the house and into an elevator. Once inside, both your head covers and masks will be removed. You'll be given further instructions then."

Jack and I quickly did as we were told. A few minutes after that we both felt the car slow, then the sound of some sort of security gate being opened. If I'd had any doubts or reservations up until now, they were gone. Whoever this mysterious woman was, she obviously did have a lot of money at the very least.

Seconds later the car pulled to a stop and I heard the sound of the front doors opening, then closing. Then someone opened our door, and I felt a hand on my arm. "If you'll step out please?" The gruff sounding voice asked. I soon heard Jack being helped from the car in much the same way as I had been, then felt it as someone placed some other type of head covering over my head effectively shutting out what little light there had been to begin with. We where then led up a short walk to a door, escorted in, where the sound of some sort of tile beneath my feet gave an echoing ring to what have must have been an enormous entry way. The next thing I heard was the sound of an elevator door opening.

"Please step inside," we were told. "Once the door has closed, you may remove your masks, at that time you will also be given some last minute instructions. Please follow and obey them to the letter, or you could be bodily harmed!"

Personally, I wasn't too fond hearing that, but simultaneously, I also heard the elevator door closing, and quickly removed the head covering, and then the blindfold I'd been wearing. There was a box on a stand next to us, and Jack and I both dropped the coverings in there. Though we looked at one another waiting for our eyes to readjust to the light, we merely grinned saying nothing.

"Please be aware, you will be watched and monitored at all times. Should you make any effort whatsoever to learn the identity of your hostess, you will be immediately and bodily removed from the premises. Beyond that, you are invited and encouraged to enjoy yourselves in whatever manner or fashion that you desire, within reason, and along with whatever additional desires or requests that your hostess might ask of you."

At that point the elevator actually began to move up, stopping a few short floors later, finally opening. Much to our surprise, we were met by an older, kindly faced gentleman who was wearing a very typical butler's uniform. He stood holding a folded terry-cloth bathrobe for each of us, atop of which sat a pair of expandable slippers.

.... There is more of this story ...

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